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Sep 15 2014
On The Cover Of A Magazine: Madonna's 200+ Greatest Magazine Covers Comments (0)
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Above: A gallery of 30 more, unranked Madonna mag covers! 

Unlike any star since—and unlike only a precious few before—her, Madonna has made the act of being on the cover of a magazine into an art form. A gung-ho participant in creating a visual record of her beauty, her aesthetic, her political and quasi-punk challenging of social norms and her status as a visual icon, Madonna has always taken her covers seriously, in some cases as seriously as other rockstars take music videos or even albums.

As a rabid collector of Madonnabilia, I specialize in ephemera, especially in magazine covers. I would hate to be presented with a calendar and shown exactly how many months of my life I've spent tirelessly pursuing new, old and new-to-me old magazines with Madonna on their covers, valuing some for their uniqueness (she posed specifically for the cover!), some for their status within her career (it was her very first time on a cover!), some for the exotic nature of their home countries (Japan! Japan! Japan!), some for being totally weird (ugliest Madonna cover ever!) and some just for the sake of fulfilling my desire to have one of everything.

Song Hits May 87 copyChoosing Madonna's best covers took forever, and it will take another forever for us to duke it out in the comments over my rankings, over which ones I forgot, over which ones I personally detest and excluded on purpose...these kinds of lists are a recipe for dissent.

But if you're into this shit, you're into it, and the time spent is as good as the time spent inhaling and exhaling oxygen.

V Summer 2014Madonna's still causing a cover commotion in 2014...

Please enjoy this list, and please comment on it. If I have forgotten any major ones, I'll happily amend my list. And if you have Long Island's Nightlife and/or Hamptons '85, I'm all ears and am ready to buy them.

Each entry contains the magazine's title, the country (it's the United States unless otherwise specified), the date of publication and then a credit for the cover photographer. In cases where I was unable to quickly determine the ID of the shooter, it's listed with a question mark. If you think you have info on any of who any of these photographers may be, I'm all ears for that as well.

One more thing: This 32,000-word post is my gift to you. But I would appreciate it if you would consider contributing any amount to my Kickstarter so that I can produce a 20th anniversary edition of my book Encyclopedia Madonnica. Click here! Tell your friends!

Thanks! Now, on with the list...


Starline 1987  copyShe's the one you're/Dreamin' of...


Starline Presents A Tribute to Madonna and the Pop Music Queens of the '80s (1987) by Herb Ritts

This cover might not look as exciting to a non-American Madonna fan, but since U.S. Madonna worshipers were not given the official “True Blue” music video (instead, we were serviced a fan-made video, the result of an MTV contest), images from that video are somewhat more exotic for us.


This special Starline issue contains a wealth of early Madonna images (though very few are out of the ordinary), and also squeezes in some coverage of Cyndi Lauper, Tina Turner and other '80s ladies. Publishers would sometimes put out specials like these in order to capitalize on the hotness of a current star, and then introduce a few other stars into the mix just so the main focus—in this case Madonna—wouldn't be able to sue them for creating the appearance of an official magazine.

As a sidenote: It takes a lot for Madonna to sue someone. It takes very little for others to sue Madonna.


199 MLC March April May 87 copyFans in 1986: “Madonna looks...different.”


MLC (Canada, March/April/May 1987) by Deborah Feingold

A 1986 pose from director James Foley's “Papa Don't Preach” video—in which Madonna unveiled her first major re-invention—was used as the fetching first cover of the Xeroxed fanzine MLC. Hard to believe, but there was no fan mag for Madonna until several years after her first single release. MLC was a worthy, if unauthorized, kick-off title, featuring collectibles (this magazine is where I first saw the fabled Japanese promo calendar with images by Curtis Knapp), unusual pictures, news (back then, news was so dated by the time it was printed it should've been called olds) run by a husband-and-wife team, the Weinzettls.

Peter Weinzettl pointed out that the magazine—which was in publication for over five years—was a success because they had no competition, but it was also a hit with fans because it was by us and for us.

Linda Weinzettl, speaking at the first-ever Madonnathon in Southfield, Michigan, made a point of saying, “She's our favorite star, not necessarily our favorite musician.”


198 Ongaku Senka June 85 copyHow often do you see Madonna in sneakers?


Ongaku Senka (Japan, June 1985) by Deborah Feingold

Madonna's session with Deborah Feingold led to some truly classic images—you'll find many examples on this list as you read, along with a bit more detail on her work.

In this case, Madonna demonstrates her remarkable ability to chew gum and work a lollipop at the same time. Cute but deadly, like that little dinosaur in Jurassic Park (1993).


197 copySinging “Holiday” while resplendent in Downtown funereal Goth-girl chic


Mais (Portugal, 1985) by ?

I'd never seen this magazine until a couple of weeks ago, when it sold on eBay, but I had to include it because it's such a bizarre cover—it looks like a blown up Polaroid, like a test shot for the outfit...Madonna's not even looking straight ahead...and she is reversed.

This image appears to have been shot while Madonna was backstage before or after her performance of Holiday on Solid Gold in 1984. That's such an unusual track performance for her in that she didn't have her own backup dancers and didn't perform alone, but instead was forced to dance and sing/get up and do her thing in front of the iconic (in the bad way) Solid Gold dancers, all of whom look like they're auditioning for the John Travolta flick Perfect (1985).


FM FAN 1984 copyGot her covered


FM Fan (Japan, December 3—December 16, 1984) by Steven Meisel

Hey, look, this is just a magazine with Madonna's second album's cover art stuck directly onto its cover. That makes for a design statement that isn't exactly exciting, and's from Japan and it's a legit full cover from 1984—there are only a handful of mags on whose covers Madonna appeared prior to 1985. Therefore, this is a must-own.


195 City Entertainment 2 20 3 5 97 copy


City Entertainment (Hong Kong, 1997) by David Appleby

For me, the most important Evita-era magazine covers are the ones with quirky images—those widely distributed portraits that were everywhere quickly lost their appeal for me. I've never seen this picture on the cover of any other magazine, and all the text just accentuates the film's international appeal.

I believe all set photography is credited by David Appleby, unless this image is a screen grab. It's definitely from one of my favorite scenes in Evita: “I'd Be Surprisingly Good for You”.


194 Elle 2 06 copyHit the “Rhoda”


Elle (February 2006) by Gilles Bensimon

Madonna's head almost looks placed onto someone else's boy-body-with-boobs here, but there's also an essential prettiness to it—I think it could be argued that Madonna was at her post-30 most attractive during the Confessions era, and the gorgeous shoot by Gilles Bensimon would be a star witness in that case.

Elle_scans_newsMore Madonna to love

In the piece inside, the writer tries to get at Madonna's anti-nostalgia, but instead gets some advice:

“The mistakes we make are as important as our successes. You can't regret it if you look back and think, 'What can I learn from this?'”

What I learned, looking back at this shoot, is that—impossibly—a dude who married Kelly Killoren (b. May 1, 1968) was also capable of turning in a crackling-good Madonna spread.


193 GQ Taiwan 4 99 copyEverybody goes to Bollywood...


GQ Taiwan (Taiwan, April 1999) by David LaChapelle

As I explain further up the list, I wasn't a fan of LaChapelle's Rolling Stone cover of Madonna, but I do think this alternate take for GQ Taiwan is sufficiently better to be dazzling to this day.


191 Collezioni Donna .j spring summerpg copy“If that makes me a bitch, okay.”


Collezioni Donna (Italy, January/February 1995) by ?

This phonebook-sized magazine cost me $50 in NYC's Garment District back in '95, but it was worth every penny, even if I probably bounced a rent check.

Where else do you get a cover of Madonna modeling haute couture for Gaultier while cudding a sweet puppy, a puppy who had just made its entrance pushed in a baby carriage?


192 Graffiti 1985 vol 1 no 4 copyTraveling back in lime


Graffiti (Canada, Vol. 1 #4, 1985) by Helmut Werb

This early Canadian music mag called it early: “The girl they love to hate.” Though it's hard to defend a girl who'd wear a lime-green sweater with yellow fingernail polish.


190 Primeiros Toques 1995 copyShaken and stirred


Primeiros Toques (Brazil, October 1994) by Patrick Demarchelier

This Brazilian mag is a favorite for its use of this image of a thoroughly debauched Madonna, unrepentant just a few years post-Sex, still flaunting her prowess in bed.

P.S. Remember the Bedtime Stories PJ Party in NYC?


189 Spin 1998 copyThe Ray of Light years


Spin (April 1998) by Inez van Leemsweerde & Vinoodh Matadin

When Madonna dropped her most artistically sound, most exploratory and—arguably—her best album with 1998's Ray of Light, she was rediscovered by the music-media establishment and given props as a great artist. Finally. All props were later removed a decade later when she was caught in possession of a hot body and a sex drive past the age of 50.


Marrying “Veronica Electronica” (her nickname at the time) with fashion shooters Inez van Leemsweerde and Vinoodh Matadin was an inspired move on Spin's part, leading to a confident cover and a spooky, surreal interior image perfectly suited to the album at hand.


188 TV Media Austria June 26 Jul 2 1999 copy“It's not true! Max!”


TV Media (Austria, June 26—July 2, 1999) by ?

TV Media, an Austrian magazine, has published a slew of quality Madonna covers, but I like this one best as a prime example of just how stunning Madonna's Max Factor promo shots were.

Madonna-Max-FactorThe commercials were lighthearted, but her poses with Raoul Bova (b. August 14, 1971) were seriously sexy.

Much later, unretouched images surfaced showing all of Madonna's wrinkles, which I'm sure she enjoyed immensely. (Why is Madonna so prone to these types of leaks? I suppose because she's the most hated, loved and famous woman alive, all four things—including alive—at once.)

At any rate, Madonna was pretty cute even without the Photoshop facelift.


187 vogue_brasil_501 copyBlack-and-white cookie


Vogue Brasil (Brazil, December 2008) by Steven Klein

Madonna's Sticky & Sweet Tour became her #1 tour of all time, a record that may be hard for her ever to top considering how frequently she's overfished various major markets in the past decade. One of the most arresting moments of the tour was the unfurling of the video sequence “Get Stupid” (a song made up of parts from the ebullient, shamefully overlooked “Beat Goes On”) , filled with provocative and stunning images; the Madonna portions were overseen by Steven Klein, who provided exclusive photos to Vogue Brasil since Madonna was set to play five nights there.

The resulting cover is ice-cold, austere and—ironically, since “Get Stupid” advocates for the little guy—authoritarian. It's Aryan Madonna as anti-Nazi with a dash of “Mrs. Danvers”; more of the same inside.

And don't forget about the killer stems.


186 Who 10 11 93 copyThere's a sinew girl in town...


Who (Australia, October 11, 1993) by Neal Preston

As Jayne Meadows said on the Ab Fab rip-off High Society (1995), “Late thirties are hard on Italian women.” Madonna was only 35 on her Girlie Show Tour, but I always thought she looked pretty haggard, chasing a year of public scorn with a grueling touring schedule.

Madonna-AustraliaMeeting Ironmen lifeguards during her first and only Australian tour

But this cover of Who is electrifying, and Madonna—while stick-thin—retains her showgirl glamour. This is also decently representative of a rarity: A time when Madonna took a tour to Australia! She waited until she was 10 years into her career before visiting the continent with a world tour, and she's been promising to return ever since. She has so far avoided the continent for 21 years running.

Madonna typically states that the extra leg would take away time spent with her family, but the fact is that taking a huge tour to Australia is just too expensive for the pay-off.

Hopefully, Madonna will rectify this situation for her Aussie fans when she world-tours, as she is likely to do, in 2015.


185They've got her number.


Number One (UK, February 9, 1985) by Brian Aris

Number One was a popular teen mag in the UK from 1983 until 1992. Along with Smash Hits, it was an essential pitstop for any act hoping to win the hearts and minds of the teen set. Madonna was far more likely to win covers in the British teen market than the American one; the latter banked on cute boys to the exclusion of cool girls, at least when it came to covers.

The inside piece wraps up Madonna's early life, including quoting her on the positive role played by her gay dance teacher, Christopher Flynn (1930/1931—October 26, 1990).

But ultimately, it's all about that orange sweater.


184 Panorama 19 Marzo 89 copyItalians do it bolder.


Panorama (Italy, March 19, 1989) by ?

Nothing like an action shot, and it doesn't get much more action-packed than dancing in front of a field of burning crosses.


183 Penthouse Italia 87 copyZip! I'm a heterosexual...


Penthouse (Italy, October 1987) by ?

A collector could go mad trying to collect every foreign variation of Playboy and Penthouse magazines—there's no such thing as a Madonna cover of either one of them that isn't desirable in one way or another. The men's magazines really knew their stuff when it came to choosing cover images.

Playboy-PenthouseNo chance they're among Madonna's faves, but Playboy and Penthouse covers rule.

I like this hard-to-find issue with its intimate live shot of Madonna on her Who's That Girl Tour. Her hair was a bit matronly, at times, for this tour, but it's perfectly tousled in this moment. It's a great shot of Madonna doing the one thing she is almost never given credit for when her brilliant career is recounted: Singing.


182 Madonna Superstar of the Century 1996 copyEverything you ever wanted to ask about Madonna...but were afraid to know.


Biograph Presents MADONNA: Superstar of the Century (December 1996) by Eugene Adebari

This is the all-Madonna special I edited and published to coincide with the release of Evita (1996). I Madonna-Evitadon't think it's showing off to include it on the list of best covers of all time since I didn't shoot the cover, but was instead lucky enough that Madonna's publicist, Liz Rosenberg, graciously donated this stunning Eugene Adebari image from the “You'll See” video. It's not an image that was commonly found on other magazines, which was maybe one reason the issue sold pretty well. Along with another special issue called Gold Collectors Series Presents A Tribute to Madonna: Viva Evita! (December 1996) that came out at the same time (pictured), this was one of the last all-Madonna magazine specials ever published in the U.S.—there probably won't be any more unless Madonna dies young (Michael Jackson special-issue magazines sold millions of copies when he passed away)...but let's hope it doesn't come to that!

The cover was originally going to be a racy Bedtime Stories shot; I still have some promo flyers showing that variation.


181 Gioa 2 8 93 copySuits me!


Gioia (Italy, February 8, 1993) by ?

My copy of this lovely Italian magazine is still in its shrink wrap, so get a gander at what's inside right here. In this period, Madonna was, in private, sobbing over the drubbing she'd received as an actress, musician and wannabe provocateuse in the wake of her Sex-ual shenanigans, but she was bravely promoting her film overseas when this unique shot was snapped on the set of a TV talk show.

On the show, Madonna was asked about her tempestuous relationship with her fans. She replied:

“Sometimes they love me, sometimes they hate me, sometimes they're angry with me...”

And how!


*Vanity Fair March 98 copyThe kid stays out of the picture.


Vanity Fair (March 1998) by Mario Testino

Madonna-LourdesIn this issue, Madonna did something that surprised a lot of her fans—she posed for portraits with her infant daughter Lourdes at the time she was promoting Ray of Light. The interview, by Ingrid Sischy (b. ?), is filled with thoughtful examination of her status as a new mother, established singer and bored member of the glitterati.

She tells Sischy:

“I'm always running. I'm like a chicken with my head cut off. I'm making my record, planning videos, doing photo shoots. I'm doing interviews. I'm trying to take care of my daughter. I'm reading scripts for movies, and Guy [Oseary]'s calling me up, going, 'You've got to listen to this and make a decision by tomorrow morning.' And I'm like 'O.K.' I have no free time.”

Not hard to hear the rap from “American Life” germinating in her brain all those years earlier.

It's painful reading about how Madonna was geared up to appear in the movie version of Chicago (2002), which never came to pass, at least not with her in it:

“She's enthusiastic about her upcoming outing as 'Velma Kelly' to Goldie Hawn's 'Roxie Hart' in the film version of the late Bob Fosse's musical Chicago, now in revival on Broadway. 'I can do 'em in my sleep,' she says of the Fosse-style dances. The project looks like it's a go. 'I think it's happening,' she says. 'It's just been a really long process of finding the right director, and I think pretty much we've found somebody, but it's not a hundred percent sure.”

The man they'd found, Nicholas Hytner (b. May 7, 1956), was not the man who wound up directing. That was Rob Marshall (b. October 17, 1960), who seems to have fired Madonna and Goldie (b. November 21, 1945), going instead with the younger Catherine Zeta-Jones (b. September 25, 1969)—who I think sucks in the movie, despite winning a frickin' Oscar for it—and much younger Renée Zellweger (b. April 25, 1969), respectively.


179 Look In 6 1 85 copyYou are the one.


Look In (UK, June 1985) by Deborah Feingold

Feingold's 1983 session got a lot of use once Madonna broke through in 1985, but I like this shot in particular. It's Confrontational Madonna at her best...and she still looked about as threatening as a Chihuahua. (But those dogs can really bite.)


178 Kinejun 1990 copyWarren's piece


Kinejun (Japan, December 1990) by Herb Ritts

This Japanese film magazine had a far better cover than the crappy one used by America's Premiere a few months earlier. Madonna's stare is killer in this uncommon (not exactly rare, not exactly one of the more oversaturated images) “Breathless” snap.


177 Interview april 08 copySquat are you lookin' at?


Interview (April 2008) by Steven Klein

HardCandyAlbumCoverMadonna was a bit obsessed with boxing, considering her Klein and Tom Munro shoots from this era. She was also rather stuck on spreading her legs—this cover along with her Hard Candy cover seeming to stress her...secret garden.

Some fans are turned off by this tough cover. To me, it has a “Die Another Day” ferocity, but she still looks hot. I actually think it would have been a better and less controversial Hard Candy has more context.


176 Hits 9 10 90 copyThe video vanguard herself


Hits (September 10, 1990) by  ?

This is my lowest-ranking of several examples of Hits that made my list, but there was never any question I'd leave it me another magazine whose cover captures the moment Madonna, appearing at the MTV Video Music Awards, cattily gave closeted George Michael (b. June 25, 1963) an award while referring to him as a “diva.”

That same evening, Madonna gave the world its first taste of her take on vogueing: She incorporated a vogueing break  into a sensational live performance of her #2 smash “Express Yourself”. Madonna was apparently proud of this night—when it was time to tweak Lady Gaga over her sound-alike “Born This Way”, Madonna's official YouTube account suddenly uploaded this, and not her official music video for “EY”.

I think this has gotta be in Madonna's Top 3 live, live-vocal performances.


Elle UKMay 2008 copyShe's got a lot of rope...


Elle (UK, May 2008) by Tom Munro

One of Madonna's most forgettable music videos, especially in comparison to the potential of the song, has to be “Give It 2 Me” by Tom Munro. At the time it was shot, Madonna posed for fashiony shots by Munro that went to lifestyle magazines and that were also used to promote her Sticky & Sweet Tour.

Tourbook-sticky-sweet-outtakes-tom-munro-35This Steven Klein-esque shot by Munro is much more up my alley than his more standard beauty shots.

Canteen_fantasy_8Never been a big fan of Munro's work with Madonna. I do think his boxing-themed stuff is pretty raw (I always liked the severe bangs on that wig...nobody else seems to), but his shoot of Madonna and Andrea Riseborough for Harper's Bazaar (December 2011) was distressingly literal and most of his work shot the day magazine #175 was shot is pretty unspectacular. Maybe it's Madonna's fault, as I think Munro's work for her recent L'Uomo Vogue—which coincides with Madonna looking less cheeky than she had in 2008—is much more exceptional. I didn't rank the latter magazine only because it's so recent. Maybe in an update!

I do like this particular cover and image. I like the tension between Madonna and the rope. It has a Betty Grable quality to it, minus the J.Lo floppy hat.


174 Asahi Graph 6 26 87 copyReturning Japanese: Madonna hits Japan in '87 for the first time in two years.


Asahi Graph (Japan, June 26, 1987) by ?

With so many portraits of Madonna flying around in 1987 (don't forget that a fresh batch of what would be free hand-out images would have been serviced to news outlets in advance of her tour), it's unusual to find a magazine that blew those off in favor of a candid snapped at the airport. 

CHris-FinchFinch (L to R) as a teen, in 2003 and in 2013. He should be about 40 now.

This image of Madonna arriving in Japan to kick off her Who's That Girl Tour has a great sense of motion thanks to the blur, and also has a bespectacled (and be-excited!) Chris Finch, her cutie-pie dancing partner on tour, just over her right shoulder.

That's-breath? Kinda unregal. But at least no one handed her hydrangeas.


173 2 Thailand January 2006 copyBending over backwards now, would you be pleased?


2 (Thailand, January 2006) by Steven Klein

This oversized publication bears a wonderfully abstract Klein shot of Madonna from her Confessions on a Dance Floor packaging shoot. A frame is in order.


172 Sky 5 89 copyWas Madonna one of “Italy's baby gangsters”?


Sky (UK, May 1989) by Arthur Elgort

Examples (and details) of Elgort's images of Madonna being used on covers appear further up this list, but this cover sure is a keeper in its own right. Ravishing in red.

For the better part of a century, magazine editors have lazily used “so-and-so talks!” to hype simple interviews; it goes back to Greta Garbo (September 18, 1905—April 15, 1990), whose fame as a silent-movie star was on the line when she made her first talkie, 1930's Anna Christie. At that time, the movie's PR guys used “GARBO TALKS!” to hype what was legitimately a remarkable thing...for the first time, her public would hear Garbo's seductive, Swedish-accented voice.

Madonna had done plenty of talking by 1989.

Great photo, though!


171 Sunday Times The Magazine 2 5 95 copyFrozen stairs


The Sunday Times: The Magazine (UK, February 5, 1995) by Mario Testino

Madonna's '90s Versace campaign, shot by Mario Testino, was multi-tiered, created across different years. There were images of Madonna with medium-length, streaked hair, wearing a partially plastic gown, and also some witty platinum-blonde set-ups portraying Madonna as a rich mom, as a busty socialite listening intently to a Great Dane and, in this wickedly beautiful pose, as a modern-day “Sleeping Beauty” who's just bitten into a poisoned apple.


170 TV Sorrisi e Canzoni feb 7 13 93 copyDo I make you thorny, baby?


TV Sorrisi e Canzoni (Italy, February 7—13, 1993) by Wayne Maser

Let's just say that Madonna was feeling a little persecuted after the wave of negativity over her sex-obsessed 1992 creative output, so she donned a literal crown of thorns for Maser in a shoot that would also include Madonna chomping on a huge cigar. The same shoot also led to a Newsweek cover (see higher up this list), and probably helped Madonna decide to work with him again—for a very famous Esquire cover (also further up the list).

I am not fond of Madonna or anyone who has not been nailed to a cross presenting themselves as comparable to Jesus, but this usage of this image is great design.


169 Tiger Beat 12 87 copyRed alert


Tiger Beat (December 1987) by ?

From 1985 on, Madonna was of interest to American teen magazines, but not being a girlish boy you'd secretly love to cuddle, like Kirk Cameron (b. October 12, 1970)—then, not now—she rarely achieved full covers. She was more likely to get a full, special issue devoted solely to herself than she was to steal cover acreage from anyone with a Y chromosome.

This lively Who's That Girl Tour cover is a rare example of the latter happening, and it appears to have happened mostly because the magazine was able to secure a second-rights interview. Interestingly, the stars who received cover chips (small photos on the cover) on this particular issue are all still active. Unfortunately, two of the stars mentioned on the cover by name are already pushing up daisies.


168 TV 11 27 to 12 3 96 copyVeil away, veil away, veil away...


TV (Germany, November 27—December 3, 1996) by ?

Madonna's scarlet Givenchy gown at her Evita premiere was a little haute couture for the masses, but this cover makes the most of it. She looks happy and radiant in red. Definitely my favorite Evita-premiere shot.


167 Madonna the Spirit and the Flesh 85 copyLove makes the world go 'round, but lucking into having Madonna appear in your student film is pretty cool, too.


Madonna: The Spirit and the Flesh (1985) by ?

A rare Live Aid cover, this one-shot by Signet is highly desirable to own thanks to the scads of rare images of Madonna from her pre-fame movie debut, the student film (I hope the director flunked) A Certain Sacrifice (1979/1985), that are inside.


166 Madonna Flaunt It 1985 copyIf ya got it...


Madonna: Flaunt It! (UK, 1985) by George Holz

Borderline_madonna_us_vinylIn the infancy of Madonna's career, she posed for some interesting photos taken by George Holz, photos in which she is dressed in all her flashy-trashy Boy Toy regalia, but which nonetheless have the vibe of old-school Hurrell of Hollywood glamour portraits. So classy were these images that one was used on the cover of her debut album when it was released overseas as Madonna: The First Album. The shots were also used for her “Borderline” single.

Starblitz-MadonnaMore examples of Starblitz mags

In 1985, as Madonnamania swept ev-uh-ry nay-shun, a publishing outfit called Starblitz in the UK specialized in producing quickie Madonna one-shot magazines. There are quite a few of them out there devoted to Madonna, all worth owning, but I like the cover of Madonna: Flaunt It! best. Not a typical teen fan-mag cover image, eh?


165 Like a Fanzine vol 1 issue 2 winter 90 copyFlag hag


Like a Fanzine (Volume 1, Issue 2, Winter 1990) by Bernard Belair

In 1990, Madonna and her Blond Ambition backup dancers José & Luis (who aspired to be singers in their own right) cut a humorous PSA on behalf of Rock the Vote, at the end of which Madonna warned:

“And if you don't vote, you're gonna get a spanky!”

This played off of her contemporaneous hit “Hanky Panky”. No word on how many spanks Madonna received when she, herself, neglected to vote in the very next election. She had never even registered in her entire life. But then she made good by doing another PSA in 1992 and owning up to her laziness while sending up her diva attitude (and referencing the fact that most of her Blond Ambition dancers had since sued her ass over their unpaid inclusion in Truth or Dare):

Love Bernard Belair's snaps of Madonna on the set—nothing elaborate, but she was a real sex kitten at that point. Madonna's official fan publication, renamed Icon an issue later, really scored with this cover. Wanna see the rest of the issue? Click here.


164 LaserVision 10 87 Hiro Ito copyShe's got the moves, baby.


LaserVision Quarterly (Japan, October 1987) by Hiro Itoh

There aren't zillions of magazines with live shots from the Japanese leg of Madonna's Who's That Girl Tour, and this one is so fetching I was thrilled to find it 25 years after it was published.

Ito had shot Madonna during her early promo-tour visit to Japan as well as live. I especially love a poster made from his work that was offered in a March 1985 copy of Ongaku Senka.


163 Juke 9 28 85 copyLog cabin fever


Juke (Australia, September 28, 1985) by Helmut Werb

Madonna's been on the cover of this Aussie music mag a number of times, but I like this early and offbeat and uncropped Werb shot the best.

Inside, the magazine attempts to figure out if or why she's the pop princess of the '80s. Gotta love this part:

“Is she as pure as the driven slush? Is she as cold and calculating as the portrait the world media has painted?”

Nice live shot by Nancy Kaye awaits inside as well.


162Her bosoms will float.

#162 TIE!

Vanity Fair (October 1992) & Glamour (France, November 1992) by Steven Meisel

I really could not choose—this Vanity Fair flirted with a major taboo (she looks like a kid, or at least a kid with big boobies), but the Glamour, on which she looks like Barbara Eden, is just so much sweeter, even with the horrible job silhouetting her hair around the logo.

The risqué VF cover made a lot of news at the time, including an Entertainment Tonight piece that forced John Tesh (b. July 9, 1952) to say words like “sadomasochism.”


161 Hits 1 14 91 copyPermissionary position


Hits (January 14, 1991) by Stephane Sednaoui

You will find another example of Hits higher on this list, and you will find another example of Sednaoui's “Justify My Love” photography higher on this list, but this is still a scorching-hot cover. You can't see her hands, and you gotta believe there's a reason.

The song and video were so instantly everywhere, it was only natural for Madonna to help spoof it on Saturday Night Live.


Important programming note: This was the era of “Rico Suave” by Gerardo (b. April 16, 1965).


160 Icon Vol 2 issue 3 number 7 copyAlways comfy with a big top


Icon (Volume 2, Issue 3, Seventh One, 1991) by Brian Hamill

Madonna has had the good fortune to work with some of the most accomplished actors and directors in history. She has had the misfortune of working with them in pieces that were not always their best: George Harrison (February 25, 1943—November 29, 2001) producing Shanghai Surprise (1986); Sir John Mills (February 22, 1908—April 23, 2005) acting in Who's That Girl (1987); Julianne Moore (b. December 3, 1960) acting in Body of Evidence (1993); Spike Lee (b. March 20, 1957) directing Girl 6 (1996); John Schlesinger (February 16, 1926—July 25, 2003) directing The Next Best Thing (2000); the list goes on!

SfIn 2013, Mia Farrow tweeted this never-seen pic of Madonna on the set of Shadows and Fog with Mia's kid Ronan.

Madonna-and-Woody-Shadows-and-FogAnother case in point: Madonna didn't get Manhattan (1979) Woody Allen (b. December 1, 1935), nor did she get Blue Jasmine (2013) Woody Allen, she got Shadows and Fog (1991) Woody Allen...dammit, his next three movies were brilliant!

Kidding aside, the movie—an Expressionist pastiche—has much to recommend it, and the experience did afford Madonna the opportunity to work in scenes with John Malkovich (b. December 9, 1953).

A news item claimed Madonna's acting was so stinky that Allen had cut most of it out of the film, like cancer, but Allen defended his actress's ability in the press.

Still, the film is not regarded as one of his best, nor even as one of his most interesting. If a Woody Allen fanatic were asked to name all of his films in 10 minutes or less, he or she would be forgiven for forgetting this one.

But the portraiture of Madonna as circus performer “Marie” by Brian Hamill that emerged from the project is decidedly soft compared to many of Madonna's poses, and therefore anything but forgettable. Much of Hamill's shoot was hard to find until the Internet, you know, happened.

Icon, Madonna's official fan publication, offered this, the most recognizable image of Madonna from the film—it's one of the only magazines you'll ever see with a Shadows and Fog Madonna cover.


6a00d8341c2ca253ef01a511d476eb970c-800wiLike the sun I never had...


Interview (June 1993) by Herb Ritts

Madonna was allegedly toast in 1993 following her successful (but off-putting) release of Sex (1992) and her unsuccessful (and off-putting) release of Body of Evidence (1993), yet she soldiered on, releasing singles and preparing for a scaled back (ha!) world tour in the fall.

Madonna-Girlie-Show-BookThis Interview cover came at a time when her face probably was not selling as many magazines as it had two years before.

The cover itself is quintessential Ritts—look at the light on her face! Inside, Ritts tried several different approaches—a somewhat unconvincing floral summer dress, totally convincing sepia-toned '40s-style Barbara Stanwyck (July 16, 1907—January 20, 1990) poses, funhouse-distorted goof-offs—and wound up shooting some images Madonna would use for the aforementioned Girlie Show Tour (1993), including as the cover of a book about the tour, and as PR images to promote the release of her semi-hit single “Rain”.


158 Bravo 9 26 85 copyThe cover's 29 years old, but Madonna, George Michael, Sylvester Stallone, both Eurythmics & Depeche Mode are still working!


Bravo (Germany, September 26, 1985) by ?

Just as Smash Hits was the go-to teen mag in the UK, so is Bravo the grandmother of all teen mags in Germany. Madonna's been on it and in it so many times it's almost pointless for any collector, no matter how fervent, to be comfortable in saying he or she has every single appearance.

Madonna's adorable, no-frills smile (it's as if she had no time to really think about how to pose here; for sure she had no clue it would be turned into a cover) was shot during her brief 1983 promo tour of the country and has never shown up anywhere else as a cover.

You can see the issue's contents here.


157 7 paris 9 26 to 10 2 90 copyBelting the “Breathless” blues


7 à Paris (France, September 26—October 2, 1990) by Herb Ritts

Isn't this a wonderfully atmospheric (aka, blurry...but on purpose) cover by Ritts? Madonna's character shimmers mid-note, which perfectly illustrates how she—as a tiny cover line suggests—hovers between wanting “Dr. Tracy” and Mr. Beatty (b. March 30, 1937).


GIrls-of-Penthouse-Madonna-nudeOn her side


The Girls of Penthouse (September/October 1988) by Bill Stone

Publisher Bob Guccione just couldn't resist using Madonna's pre-fame nudes (in this case, shot by Bill Stone—more here) over and over again on covers. I recall buying this at a convenience store in my hometown of Flushing, Michigan, where I'd grown up. I was 19 years old but felt like a total perv buying a porn magazine from a middle-aged lady who had seen me buying 25-cent candy bars in the same store throughout my childhood.

This special edition of the porn rag has an especially nice shot on the cover, so dreamy and romantic...a far cry from some of those hairy-underarmed photos of Madonna taken during the same period that people make fun of to this day.

You'll find more of Bill Stone's work and more Penthouse covers elsewhere on this list.


GOldmine copyCollect 'er? I hardly know 'er!


Goldmine (July 24, 1992) by ?

An androgynous “Open Your Heart” on-set pose appears on Madonna's first Goldmine cover. The feature inside is an exhaustive piece by mega-fan Bruce Baron, which laundry-lists Madonna musical trivia the likes of which fans had never seen gathered all in one place. A collector's dream, and a long time coming for Madonna to have been recognized by the publication as one of the greats.


154 dem Glamour 12 90Fuller airbrush girl


Glamour (December 1990) by Patrick Demarchelier

Demarchelier took a cool, vampiric glamour portrait of Madonna for the cover of Glamour's “Women of the Year” issue, but the magazine's creative staff played God, giving her a tan, making her hair more yellow, brightening the whites in her eyes, bonding the gap in her front teeth...what didn't they change about the image?

Glamour-Madonna-DemarchelierA similar shot, retouched (check the neck and chest) but before the mag got a hold of it.

Madonna was reportedly unimpressed, and did not attend the magazine's party for the issue. It's still a classic cover.


152 madonnahightimesmag copyAlways thought Madonna looked very Marlene Dietrich (December 27, 1901—May 6, 1992)-esque here


High Times (May 1985) by Herb Ritts

Though the cover suggests otherwise, the actual feature inside the pot-smoker's bible is an interview with Desperately Seeking Susan's director—not its stars!—Susan Seidelman (b. December 11, 1952).


153 April 1989 copyCornered


Spin (April 1989) by Herb Ritts

I kind of think Spin got the least spectacular of the Ritts Like a Prayer portraiture for its cover, but it's still nice enough. You can totally smell the patchouli, no?

Inside, while talking about the “New Madonna,” the magazine never gets a quote from the woman herself, instead having to use her latest album and poses as clues.


151 Music_Connection_Magazine_March_1985_Cover_with_Madonna copyExperience soon made her rich.


Music Connection (March 28—April 10, 1985) by Mary Lambert

This isn't a very high-quality screen grab from Madonna's high-quality music video “Material Girl”, but I like offbeat covers like this. Also, any Madonna cover from 1985 or earlier is a keeper.


150 People 5 13 85 copyThe last time Madonna had even the slightest amount of body fat anywhere near her mid-section, not counting pregnancies.


People (May 13, 1985) by Neal Preston

Preston, a veteran event photographer, has shot Madonna often over the years. His first major Madonna cover was her second People cover of 1985, documenting the wildfire success of her first tour.

How can you not adore a magazine that coins the term “MAN-SMASHER” on the cover?

In the piece, Madonna is quoted as referring to friend Prince (b. June 7, 1958) as “the midget”; she may have been a little more magnanimous and a little less of a cunt considering how inspired by Prince her Virgin Tour paisleys were.


149 Bild + Funk Ger 9 13 85 copyBracelet yourself for impact!


Bild + Funk (Germany, September 7—13, 1985) by Ken Regan

This is one of quite a few covers to make my list that are from Ken Regan's 1985 People session. (You'll find that particular mag higher up this very list.)

Did you know that her rubber bracelets, mimicked by wannabes everywhere, were designed and manufactured at Madonna's stylist Maripol's (b. 1950s) direction? They're not just hardware-store stock.

Speaking to W in 2010 on the occasion of her partnership with Marc Jacobs (b. April 9, 1963) to design retro-'80s pieces in her inimitable style, Maripol said:

“I understand why the antiglobalization protesters are there. Even back then, banks wouldn’t lend me a penny. If one of them had, I’d be a multi­millionaire now from my rubber bracelets...

“Originally I thought of them as antiwar symbols, because soldiers in Beirut used black rubber bands to tie up their things. And I liked the idea that you didn’t have to take off your bracelets to get into the shower...

“Remember the look-alike contests? It was great, but that’s when I started getting copied, so that part wasn’t so great. It’s flattering, but not when you’re not making any money from it.”

Show of hands: Who wishes they'd had the money to lend Maripol back in the day?


Screen Shot 2014-07-21 at 6.58.12 PMGotta hands it to her...


Q (UK, March 1998) by Rankin

I think Madonna's work with Rankin is an interesting counterpoint to her Ray of Light Mario Testino packaging—it's much more grounded and earthily erotic (those nipples!). I love this cover because: Are the bitten hands a sign of a pensive or a raring-to-go Madonna...what is she hiding?


147 Billboard 9 11 99 copyIt ain't over until the skinny lady sings.


Billboard (September 11, 1999) by David LaChapelle

I'm not the fan of LaChapelle's I was when I first discovered his work and owned an early image he'd taken of his late assistant, but then, LaChapelle is not the fan of Madonna's he was before they worked together a few times, either.

After shooting her for Rolling Stone [she looked like Kirstie Alley (b. January 12, 1951) on that cover, post- post-production] and for this fab Maxfield Parrish-ish (July 25, 1870—March 30, 1966) MTV Video Music Awards promo image that graces the cover of Billboard, he was set to direct her “Hung Up” video in 2005, but decided she was too “nasty” to have to deal with. The New York Times reported in 2011:

“When, in the middle of a telephone call from Madonna, the singer began haranguing him about a video the two were planning, Mr. LaChapelle suddenly took the mobile phone he was holding away from his ear and snapped it shut.

“'My agent was shocked,' he said. '“Did you just hang up on Madonna?” It was a pivotal moment in my life, because it was the first time I said I don’t want to do this anymore.

“'It was liberating,' he added, 'to think that I didn’t have to work for pop stars or magazines anymore, and that I would never have to shoot the latest video by Britney Spears again.'”

LaChapelle was still talking about Madonna's nastiness in 2014.

His gain is our gain; the video wound up being a worthy addition to her catalogue, and quite possibly her last truly great clip before she seemingly lost interest in the medium.


23323439-23323585-large copyCowgirl, you got Ciccone-mail


Rolling Stone (September 28, 2000) by Jean-Baptiste Mondino

Looking like Judy Collins (b. May 1, 1939) with an Urban Cowboy (1980) cowgirl hat, Madonna appeared on Rolling Stone at the time of her Music album's assault on the charts.

“Music”, the single, is her most recent U.S. #1 hit. That just ain't right.


146 Forbes 10 1 90 copySeeing dollar signs


Forbes (October 1, 1990) by ?

Though a variety of Forbes writers take turns denigrating Madonna currently, there was a time when the mag was high on her biz acumen. In 1990, the magazine's surprise use of her on a cover and its close examination of her affairs was at least in part responsible for what is one of the longest-running (and not necessarily least true) clichés about Madonna: That she is one heckuva businesswoman.


145 Special Report 11 89 1 90 copyNever forget your roots.


Us (September 7, 1987) & Special Report (November 1989—January 1990) by Alberto Tolot

Screen Shot 2014-07-21 at 6.26.08 PMMadonna was promoting her 1987 Who's That Girl movie and tour when she talked to Us, but the juiciest part of the story is when Sean Penn (b. August 17, 1960) shows up:

“Back at the restaurant on Sunset Strip, 'the coolest guy in the universe' has made his appearance, arriving with the director of photography for his upcoming film Colors (a cop story directed by Dennis Hopper). He's wearing a sport coat, a tan, a short haircut and a half-grin. 'The interview stops here,' he says, but then talks amiably enough about a mutual acquaintance. A few minutes later, Sean interrupts Madonna to complete a story without realizing it's going onto the tape. When he sees the reels turning, he grabs the machine and maladroitly tries to find and erase his words. But the tape recorder has no speaker, and as he finds himself stymied, there's a lingering, unamiable pause. Finally, he hands the recorder back, unharmed.”

Imagine a 2014 issue of Us with a story containing the word “maladroitly”?

BarbramadonnaI love Special Report, even though it came out a couple of years later, because it's huge and the magazine didn't last long. The gimmick was that the magazine had a whole different slant each issue, this one being on personalities. It takes issue with comparing Madonna to Marilyn Monroe (June 1, 1926—August 5, 1962):

“If one were to make comparisons, Madonna seems closer to Cher (boldly honest and frankly sexual) and to Barbra Streisand (toweringly ambitious, sure of herself, with a great desire for complete autonomy in her work).”

Madonna made the cover because she was, the magazine stated without hesitation, the world's biggest celebrity.


144 Sm Hits June28 July 11 1989 copyOooh, Bobby Brown poster!


Smash Hits (UK, June 28—July 11, 1989) by Arthur Elgort

Madonna was a teen idol—don't forget that! But she became so huge so fast that the teen mags desperately seeking content on her often had to run the dribs and drabs of what larger publications were running because...c'mon, do you think Madonna was going to cooperate with teen magazines once she'd been on Vanity Fair?

This issue of the legendary Smash Hits is a great example of how to work around Madonna—you pay second rights fees to fashion photographer Arthur Elgort for a great picture of her not used when he shot her for an inside (!) feature for a blink-and-you-missed-it mag called Fame (December 1988).

I wonder what the fee was back then? When I ran a teen mag in the U.S., a large set of 100 unused High School Musical (2006) portraits, being sold for unrestricted second-rights use, went for about $100,000. I imagine Madonna, Inc., had the right of approval when it came to Elgort's shots, so they probably kindly allowed Smash Hits to use this one for a reasonable rate.


143 Vogue10 92 copyWearing clothes, for a change


Vogue (October 1992) by Steven Meisel

I actually vastly prefer the Italian Vogue with an alternate cover from this shoot (it's further up the list), but there's no doubting how great Madonna looks in her hippie gear...and how off-brand, and therefore singular, this cover is.


142 Qjpg copyAt this point, she was an American wife


Q (UK, May 2003) by Craig McDean

The American Life era was a hard one when it came to all-time classic magazine covers, but I managed to include some on this list.

This one does a good job of camouflaging how unflattering all the war gear was—there is a glamour to it, as well as an edge. Of course, most of her facial features are scrubbed into non-existence, but they're still nice pictures.

The tranquility of the images—which look like the satisfied aftermath of some surreal conflict—are still a far cry from how unbelievably daring her original “American Life” music video was; it would've been more organic for Madonna not to have been so prettied up in the accompanying imagery.


141 Sound & Vision International July Aug 90 copyMother of Pearls: Sinewy Madonna as “Hortense Hathaway”


Sound & Vision International (July/August 1990) by Paula Court

Madonna is practically synonymous with bad acting on the big screen. Sofia Coppola (b. May 14, 1971) comes to mind, too, but can you think of many other actors who were given so many chances to be good, and who were called outright bad over and over?

In point of fact opinion, Madonna's actually given some fine performances—at least as many good as bad—but because she has appeared in so many creaky vehicles over which she has had too much control, and because Madonna is not a gifted actress but rather like a wild pitcher, some of her most (in)famous film performances have also been her worst.

Madonna-Bloodhounds-of-BroadwayI would argue that one film for which Madonna was neither crucified nor lionized, simply because it was so small it came and went, is Bloodhounds of Broadway (1989)—and both it and she in it are utterly charming. (Okay, she got a Razzie nomination, but they always nominated her and would have done so even if she'd walked in front of a movie camera accidentally.)

Directed by Howard Brookner (April 30, 1954—April 27, 1989), who died of AIDS before it was released, Bloodhounds of Broadway is based on several Damon Runyon (October 4, 1880—December 10, 1946) short stories and features performances by a dozen famous folks. Most interesting to Madonna fans is her duet with BFF Jennifer Grey (b. March 26, 1960), I Surrender Dear.

I love this obscure BOB cover of Sound & Vision International—actually the back cover, or flip cover—because I always felt Madonna's 1920s Theda Bara (July 29, 1885—April 7, 1955) look from this film was scandalously underexposed since the film itself barely played in theaters.

There is also a really gorgeous cover of a 2007 publication called The Knowledge with an until then never-seen portrait of Madonna by Paula Court, but as much as I like it, I tend to discriminate against covers that feature images, even unseen, so long after they were taken. I find covers with images that were current at the time of publishing—or within a few years—a bit more special.


140 Spin 4 87 copyThere's a great Ritts shot inside that also has no eye contact.


Spin (April 1987) by Iain McKell

For Madonna's second Spin appearance, the photo editor confidently uses an image of Madonna that lacks one thing most effective covers rely on in order to generate sales—eye contact. This sultry shot (which is a reverse image) has great tension and eroticism, though, precisely because Madonna's lids are at rest.

Inside, Madonna states:

“People don't want to like me. And that's because you're not supposed to be flirty unless you're an airhead...I'm doing it because I like it. If I don't like it, no one's going to. I do it because it turns me on.”

I don't believe this exact McKell shot has ever been used as a cover elsewhere, making it all the more special.


139 NY Talk Aug 85 copyThe free New York newsprint magazine is extremely uncommon to find today.


NY Talk (August 1985) by Bill Stone

This cover had the artsy gravitas to get away with capitalizing on the topical furor over Madonna's pre-fame nude modeling. I've always found it to be an especially nice example of a nude Madonna cover...even if the design puritanically covers her up.


138 Mixmag 3 2000 copyNote the red Kabbalah string on her wrist.


Mixmag (UK, March 2000) by Dah Len

Madonna had a sort of pre-Confessions on a Dance Floor look in this session with Dah Len; there is a slightly 1970s sleek, disco feel, even though she was plugging Music (2000) back then, and COADF was just a gleam in her eye.

Madonna was beginning to brace us for a long stretch of dance music, broken only by American Life (2003), saying:

“We're always dancing in my house or office or the kitchen. Dance music is in my molecular structure.”

She also speaks at length about the difference between electronic and techno music, and explains why she loves the former and hates the latter.


137 Bazaar Nov 13 copyRichardson jumped from Gaga to Madonna and lived to tell?

#137 TIE!

Harper's Bazaar (November 2013) & subscriber's edition, both by Terry Richardson

Madonna-BazaarI would hazard a guess that this remarkable cover shoot will be much higher on a list like this in a few years—I hesitated to rank such a new cover so high. But in spite of my reservations about Richardson as an artist, I think he did a fine job making Madonna look regal, sexy and yet still mature. Yes, it's Photoshopped nearly to death (and you thankfully can hardly see her gold grills), but it's pure eye candy, as is the fetishy shoot inside.

Inside, Madonna repeats her story of being raped on a rooftop in NYC, though the media reacted to it as if this were the first time it had ever been told.

The piece is in the form of an essay by Madonna, who writes with gritty determination about surviving her early years in the city that would make her:

“This wasn't anything I prepared for in Rochester, Michigan. Trying to be a professional dancer, paying my rent by posing nude for art classes, staring at people staring at me naked. Daring them to think of me as anything but a form they were trying to capture with their pencils and charcoal. I was defiant. Hell-bent on surviving. On making it. But it was hard and it was lonely, and I had to dare myself every day to keep going.”

Foreign editions and the mag's subscriber's edition use an equally nice shot of Madonna squatting.


136 Bazaar 2 99 copyWith the greatest of Japanese


Harper's Bazaar (February 1999) by Patrick Demarchelier

Madonna's so-called “WHOLE NEW LOOK” this time was a whole new race. Apparently so enchanted by the book Memoirs of a Geisha (1997) by Arthur Golden (b. December 6, 1956) that she was hoping to appear (!) in a future movie adaptation (Geisha director Rob Marshall, who'd kept Madonna out of his Oscar-winning 2002 Chicago movie adaptation, kept her out of Geisha, too), Madonna's “Nothing Really Matters” music video and this cover appearance featured her take on kabuki realness.

This sort of cultural appropriation is frowned upon more and more; back in 1999, I don't recall much, if any, of an outcry. It did lead to a fearlessly avant garde video with some fierce “Elaine Benes” dancing. (And yes, the latter's dance moves pre-dated Madonna's by just over two years.)


135 Record 5 19 84 copyMadonna was very lucky with stars.


Record Mirror (UK, May 19, 1984) by Helmut Werb

This extremely early UK cover appearance is a ton of fun inside and out, thanks in part to a fetching Helmut Werb snap.

Inside, Madonna gives a lengthy interview, one that's crammed onto one page. She previews her forthcoming Like a Virgin album by recounting a visitation from another genuine icon during the recording sessions with Nile Rodgers (b. September 19, 1952):

“Oh yeah—last week one of my idols came down—Diana Ross. She'd been recording downstairs and she and Nile are real good friends. Her kids really like my stuff so she brought a bottle of champagne and toasted my success—I was so flattered.”

Miss Ross (b. March 26, 1944) wasn't the only sweet superstar with whom Madonna was rubbing elbows back in 1984:

“You hear so much about celebrities being horrible and then you meet them and they're not that way at all. I met Barbra Streisand and she was the same—enthusiastic and encouraging.”

Streisand (b. April 24, 1942) had just had what would be her last—so far—U.S. solo Top 40 single, 1983's “The Way He Makes Me Feel” from Yentl (1983). Ross's last U.S. solo Top 40 single was right around the corner, 1984's “Missing You”.


134 ASCAP Playback Mar Apr 95 copyThe cure for what veils you


ASCAP Playback (March/April 1995) by Frank Micelotta

Rarely given proper credit for her songwriting prowess, Madonna enjoyed some love from ASCAP Playback, a trade publication, when her “Take a Bow” single became the longest-charting #1 hit of her career. Though this was 20 years ago, it was also her second-to-last #1 far. Does anyone really believe Madonna doesn't have another #1 in her?


133 Redbook 1 97 copyI always thought this session had a Barbra Streisand, I'm-a-serious-film-person feel.


Redbook (January 1997) by Herb Ritts

When Madonna committed to Evita (1996), she committed—and she promoted the hell out of the movie, doing interviews with many unexpected outlets. Many fans never thought they'd live to see the day that Madonna would grace the cover of stay-at-home-mommy stand-by Redbook (and probably many Redbook readers felt the same), but as the star of a big-budget dramatic musical that hoped to clean up at the Oscars, Madonna was a good choice for this cover.

And the photo editor made a great choice in selecting this hand-out shot of Madonna in a feminine, hot-pink top and wearing her strawberry blonde conservatively.

The interview focuses on her movie re-invention and her recent experience with motherhood. But it also touched on Madonna's aging fame. She expressed, perhaps without believing it was possible:

“Maybe in five years people won't be chasing me around as much as they do now. That would be nice.”

Dream on, white girl.


132 Rolling Stone 12 1 05 copySomeone is a big fan-Margret


Rolling Stone (December 1, 2005) by Steven Klein

Either Klein or Madonna herself was evidently on a major Tommy (1975) kick around the time of Confessions on a Dance Floor—an image that wound up on Q (further up this list) was a total Tina Turner (b. November 26, 1939) “Acid Queen” tribute, and this Rolling Stone cover is more Ann-Margret (b. April 28, 1941) than Ann-Margret.

Ann-MargretMadonna can both see and feel Ann-Margret.

The cover story goes over Madonna's fall from grace with American Life and her improbable rebound with Confessions.


Tutto Musica & Spettacolo gennaio 1990 copyA photo shoot of sketchy origins


Tutto (Italy, January 1990) by Edie Baskin

Madonna's thrilling stint on Saturday Night Live in 1985 as host (but not as musical guest—she was making a point about being an actress) kicked off what has been called the show's worst season. (Far worse was waiting down the line, IMHO.) The ratings were sensational, and Madonna's comic chops were undeniable in a variety of skits, some with better writing than others.

Madonna was hilarious croaking out “Take On Me” by a-ha in a Spanish-language-themed singing sketch, had Lana Turner (February 8, 1921—June 29, 1995) realness in a spoof of When a Stranger Calls (1979) and was brave enough to appear in a very early sketch (called “Pinklisting”) about AIDS that made fun not of the disease but of the paranoia surrounding it:


As spot-on as she was sending up Joan Collins (b. May 23, 1933) in “Pinklisting”, she was less convincing as Princess Diana (July 1, 1961—August 31, 1997) and Marilyn Monroe in other sketches.

This photo shoot by Edie Baskin was Madonna's SNL portrait session, so it's quite weird that it was recycled some five years later for an Italian cover. But that's what makes it somewhat special—the session was not used on many covers, and Madonna was just plain purdy in it.

A different shot from this sweet sesh appears on Pop Gear (Japan, May 1990) and is darn near as appealing.


130 Switch 11 06 copyOn bed with Madonna


Switch (Japan, November 2006) by Steven Klein

Featuring a pic of Madonna that originally appeared in W (slightly higher up on this list), the Photography Issue of this posh Japanese mag chooses the inscrutable, offbeat image of a Madonna sporting a cheap wig, hairpins and fishnets.

Dirty and divine.


129 Time Out London 7 10 17 91 copyTriple threat


Time Out (UK, July 10—17, 1991) by ?

Madonna's greatest live vocal ever was at the Oscars in 1991, where Dick Tracy's “Sooner or Later” was nominated for (and won) Best Song.

Unfortunately, this visually clever cover illustrates another annoying piece by annoying, war-mongering, trans-bashing provocateur Julie Burchill (b. July 3, 1959), who's welcome to her opinion, of course, but...must she have so many stupid ones?


128 TV Guide Aug 10 16 85 copyActually, proportion is a girl's best friend...but I love it all the same.


TV Guide (August 10—16, 1985) by Bob Peak

Madonna was lucky enough to be immortalized for the ultimate TV-lover's bible by Bob Peak (May 30, 1927—August 1, 1992), called the father of the modern movie poster.

Madonna-Bob-PeakThe full illustration

Peak's most famous creations include the key art for the My Fair Lady (1964) and Apocalypse Now (1979) movie posters.


127 W by Klein copyPole position


W (April 2003) by Steven Klein

Madonna's creative partnership with Steven Klein has stood the test of time. For over a decade, they have created some of her most important latter-career (well, we hope to term it mid-career one day!) imagery. More importantly, Madonna is comfortable enough with Klein that she has engaged in some time-consuming and off-the-beaten track shoots just for art's sake.

This one, which was truly mind-blowing when installed in NYC's Deitch Gallery (and which led to a you-must-find-a-copy coffee-table book called X-Static Process), was splashed across 44 (!) pages of W Magazine, showing Madonna at her least digestible, most confrontational. I mean, popstars aren't supposed to do stuff like this:

Steven-KleinHerb Ritts would have been like, “WTF???”

This era, it turned out, was not going to go down easy with the public—the accompanying album, American Life (2003), was called a bomb. But it was worth it for the music it contains, and for these Klein pictures, which even his biggest critics (fans seem divided on his contributions to Madonna's oeuvre) would have to admit are adventurous and boldly original.


126 Icon May 2005 quarterly copyI always thought this somber pose (well, there's a tombstone in it) looked like a silent-movie still.


Icon (May 2005) by Herb Ritts

In the dying days of Madonna's official fan club publication Icon, this out-of-nowhere flashback to 1989 made the cover. Never seen before it appeared in fans' mailboxes on the cover of this limited-edition magazine, the outtake from the Like a Prayer promo shoot is a shocker—it's so good, it's hard to believe it was never used in the first place. I mean, we got a picture of her fucking hands for that album's cover! The image is so grand its inclusion on my list breaks my previously stated desire to avoid magazines whose cover images were taken many years before their publication dates.


125 Q Nove 06 copyThe woman in red


Q (UK, November 2006) by Steven Klein

Q-MadonaFor its 20th anniversary, Q issued an array of covers, featuring some of the biggest music icons of all time. Madonna's cover is a devastatingly glittery Confessions on a Dance Floor-era number, clearly inspired by Tina Turner as “the Acid Queen” in Tommy (1975).

No acid queen she, Madonna—in the quickie Q&A inside—tells Q her fave drug of the previous 20 years had been a double espresso. This is also the interview in which she first references Elliott Smith (August 6, 1969—October 21, 2003) and his “Between the Bars”, a song she would cover in 2013 at her secretprojectrevolution premiere party.

Also of note, Madonna is asked what's left for her to accomplish, something her fans would have a hard time guessing. But she replies in the opposite direction:

“What's left? I haven't even gotten started.”

Well played, bitch.


124 Penthouse 9 87 copySnatching victory from defeat. (You can blame bush for the censorship.)


Penthouse (Germany, September 1987) by Herman Kulkens

Madonna posed for a series of rather literal and crudely fetishized nudes with photographer Herman Kulkens allegedly around 1977, when she was 19. Some of the naked shots made it into Penthouse over the years, but many others were never seen until its publisher's death from cancer and an ensuing auction of original slides.

It's my guess that Kulkens was going for a Bunny Yeager (March 13, 1929—May 25, 2014) knowing kinkiness, but at least in the case of this nekkid cowgirl shot, wound up with something more laughable than boner-inducing.

The image is so ridiculous, I can't help loving it. Madonna was probably wishing those boots were made for walking.


123 News of the World Sunday 6 1 86 copyField of nightmares


News of the World Sunday (UK, June 1, 1986) by Herb Ritts

A colorized portrait of Madonna and childish hubby Sean Penn that was part of Herb Ritts's highly engaging 1985 Interview (up much higher on this list) shoot is repurposed here, for a piece on all the negative rumors about the couple—were they really deserving of the nickname “the Poison Penns”?

Well, since the press came up with the name, it's not hard to guess what the press would decide upon considering that question. But as Cher (b. May 20, 1946) once told me at a Marshall Field's event in Chicago in the late '80s—just look at the pictures and don't read the articles.


122 Moda 8 90 copyWaiting to exhale


Moda (Italy, August 1990) by Herb Ritts

I don't know about you, but Madonna was the first person I'd ever heard of having her lips jacked up—and boy, were they jacked up in 1990. She seemed to luxuriate in the knowledge that her naturally thin lips could so easily (if so temporarily) be fluffed into auto-pucker plumpness.

This image comes from a famous Ritts shoot, from which images were used in Madonna's Immaculate Collection packaging.

For a woman who professes not to smoke, she does it a lot when the camera comes around.

This magazine, by the way, is thicker than Brahim Zaibat's (b. circa 1988) calling card, so expect to pay a ton in shipping if you buy it online.


121 Interview 5 89 copyShort and suit


Interview (May 1989) by Koto Bolofo

MadonnaWhen Madonna posed for Koto Bolofo in a Diane Keaton (b. January 5, 1946) white suit with pearls, waltzing up and down the beach, it produced her only posed cover to feature her short-lived blonde streaked brunette hair—she'd also posed for Vogue (much further up this list) with this look, but Vogue had airbrushed her into 100% brunettedom. Moda (Italy, September 1989) is probably the most prominent title that used a second-rights shot from this shoot on its cover.


Inside this umpteenth appearance on Interview, Madonna is interviewed by Becky Johnson about all the hullaballoo surrounding her Like a Prayer album. But my favorite quote is:

“I dislike men who totally suppress their femininity.”

I guess this is why Sean Penn had to go.


120 Icon vol 1 issue 3 spring 91 copyMadonna was peeking in 1991.


Icon (Volume 1, Issue 3, Spring 1991) by Steven Meisel

This could be one of the most overexposed images of Madonna ever taken. Shot by Steven Meisel during Madonna's Truth or Dare ramp-up, it's also compositionally masterful and captures both Madonna's personality and the character of her documentary perfectly.

Though this image was everywhere in 1991, the very first time anyone saw it was on the cover of Madonna's official fan magazine. Icon was the be-all, end-all back then, as was this portrait.


119 Hits 5 2 2003 copyBeret of light


Hits (May 2, 2003) by Craig McDean

Irreverent industry magazine Hits was not sold on the newsstand, so was tough for fans to get a hold of. I used to call them up and beg for multiples...and then sell off the overstock! Its high-end covers (the magazine was frequently able to swat down pick-of-the-litter images from photo shoots handed over free of charge by publicists eager to help their clients get coverage) were always coveted collector's items; Madonna has appeared on its cover many times, and every appearance is a winner.

Hits is now propelled by a massively influential (and oddly jokey) Web site. Print publishing...? What's that?

Craig McDean's packaging shots for Madonna's overlooked American Life album (2003) are not my favorites. In fact, I hate that album's cover, which is IMHO an embarrasssingly literal Che Guevara (June 14, 1928—October 9, 1967) tribute that comes off far more Patty Hearst (b. February 20, 1954) than anything else.

But I do love this portrait, in which Madonna looks scary-beautiful, as lithe and deadly as a cobra.


118 Ciao 2001 apr 25 2006 copy2001: A gives-good-face odyssey


Ciao 2001 (Italy, April 25, 1986) by Gary Heery

Not that long ago, if you talked about the year 2001, people thought of futuristic gadgets or maybe apes freaking out over a monolith; we didn't realize quite how close 2001 was. Now, people think of 9/11 and/or a year that happened forever ago. It's not futuristic, and it's not romantically of the past. It's just...old news.

The music mag Ciao 2001 (1968—2000) was as short-sighted as the rest of us in deciding upon its title.

I love this cover, though—and as you'll see throughout this list, I'm partial to colorized solutions to familiar or black-and-white photos. Colorizing it [in this case, in a bit of a Peter Max (b. October 19, 1937) more than an Andy Warhol (August 6, 1928—February 22, 1987), way] was a stroke of creativity that made it pop in 1986, several years after it had already been used as the cover of Madonna's debut, eponymous album.


117 Columbia Film View Summer 85 copyGot a light comedy?


Columbia Film View (Summer 1985) by Andy Schwartz

Over time, I feel like Desperately Seeking Susan (1985), Susan Seidelman's '80s take on a screwball comedy, has become misremembered as some crappy Madonna vehicle, like Who's That Girl (1987) arguably was. But in truth, it's an excellent, scrupulously paced, well-acted and inventive comedy, one deserving of the mostly very positive reviews it elicited upon release.


Pauline Kael (June 19, 1919—September 3, 2001), one of the most famous film critics of all time, said of Madonna's performance in the title (but not lead) role, that she had “dumbfounding aplomb.”

Later on down the line, though, Kael would concede:

“I thought she was going to be great fun when I first saw her in Desperately Seeking Susan, but she hasn't been great fun since. And somehow she's blown it by now. She's never really scored in front of the camera the way she gave promise of doing. There's something iron-plated in the way she meets the camera.”

I've always loved this tough-as-nails still from DSS on the cover of Columbia U's film mag, a publication that existed from 1984 (as Columbia Film Review in its first year) until 1989. Madonna does not need Beyoncé (b. September 4, 1981) to make the most of a jail scene.


116 Bazaar May 88 copyBecoming slightly dotty


Harper's Bazaar (May 1988) by Francesco Scavullo

Bazaar-MadonnaThis exclusive shoot captures a demure Madonna at the moment she was rehearsing for her Broadway debut, in David Mamet's (b. November 30, 1947) Speed-the-Plow (1988). The reviews were largely negative, but the New York Times liked her, and Madonna kept the show a red-hot ticket throughout her run with it.

The shoot bows to spring fashion. I'm not sure Madonna looks fully comfy in anything but the mauve tights and jaunty skirt, but it's great to see her in this period through the lens of someone besides a paparazzo.

Madonna-BazaarMadonna and that damned apple. (Slightly different image from the one used on Colombian Bazaar.)

The shoot also produced some fun, if awkward, covers elsewhere, such as the infamous Colombian Bazaar cover (September 1988), on which Madonna sports a pretty fruity hat.

In the interview, Madonna comments on what by then had already become her penchant for physical fitness, saying:

“There's no doubt about it. My voice, mind and body feel strong when I'm standing on strong legs.”

Madonna-theaterMadonna with (L to R) her Goose and Tomtom and Up for Grabs casts

Too bad her stage career didn't have legs—aside from Goose and Tomtom (1987), S-T-P and her (wonderful...I was front row!) London debut in Up for Grabs [(2000)...did you know Danny Pino (b. April 15, 1974) of Law & Order: Special Victims Unit (2002—) was in it?), Madonna hasn't had any other occasion to tread the boards.


115 Bizz July 90 copyTransparent motivations


Bizz (Brazil, July 1990) by Lorraine Day

When Madonna released her video for “Vogue”, she was wearing a straight-up see-through lace blouse in it. In spite of the fact that her breasts were totally visible, MTV played it without hesitation and it is played to this day on TV (on occasion) with no bars or other modes of camouflage. This lack of concern over her breasts on the part of MTV was one reason Madonna gave for believing that the network would have no reason to ban her next video, “Justify My Love”.

Day's shots of Madonna from the set of “Vogue” are, like everything associated with that perfect storm of a production, iconic, capturing Madonna at the peak of her beauty. This lovely color shot, rendered on a slant, elevates this copy of Bizz into my countdown. It's just great.


114 Bazaar 3 06 copyGetting up and doing her thing

#114 TIE!

Harper's Bazaar (March 2006) & Harper's Bazaar (March 2006) subscriber's copy, both by Solve Sundsbo

Madonna-SundsboTo promote Confessions on a Dance Floor, Madonna did an original sitting for Harper's Bazaar that resulted in two very different covers—for the newsstand, it's a sweetheart of a pose that presents Madonna as a fragile flower; for subscribers, it's a dramatic, active, modern dance-infused montage of images that plays up Madonna's artsy side.

Inside, the feature was all about the modern-dance side of things, appropriately, since she was in the midst of de-inventing herself back into a disco dolly. Madonna comes off as pretty hifalutin in the interview, raving about wines and foie gras and other not-so-down-to-earthy pleasures. But asked to write a letter to her 19-year-old self, she gets a bit deeper:

“You’re not going to believe what’s going to happen to you…But remember these things: Never take any of it personally. If you really want to be a revolutionary, you have to be prepared to be unpopular. Don’t do it if you don’t really mean it, and—what else?...None of it is real.”


113 Arena Jan Feb 99 copyNothing really matters, but nice boobs are pretty important.


Arena (UK, January/February 1999) by Luis Sanchis

Madonna-Nothing-Really-MattersThis dedicated shoot by Sanchis was a show-stopper back in early 1999, when Madonna's Ray of Light had almost lost its steam after a year-long run on the charts. “Nothing Really Matters” was her next single, and while it didn't become the smash it deserved to, it was a stand-out recording from her, one whose single was adorned with an image from this session with Sanchis. The cover image was also used on a promotional-only counterstand on behalf of the album...because in those days, there were brick-and-mortar stores that sold CDs, and those stores had counters!

Madonna New Era spoke with Sanchis about the shoot. He confirmed it was a limited shoot done in the Hilton Hotel in New York, but couldn't remember what music was playing:

“I was so busy with my assistants and you have such a little time to shoot five or six different images in a few hours that I don't remember if we had music or not. We probably had music playing. It was in the beginning of my career and I didn't have the experience I have now so to shoot Madonna I guess it was a big deal.”

I guess it was.


112 1985 copyMad, plaid and dangerous to know


? (Japan, 1985) by Mark Bourdillon

Sorry, I don't have a correct translation of this magazine's title, but in spite of that hideous plaid sweater and Madonna's purple eye shadow, I think there's something special about this pose from Bourdillon's sessions with Madonna, conducted in London in January of 1984. She doesn't look as sold on it as I am, though!


111 7 Italy 9 12 87 copyTokin' woman


7 Corriere della Sera (Italy, September 12, 1987) by Herb Ritts

Making use of a lovely image of Madonna from sessions that went on to decorate much of the Who's That Girl Tour program, this oversized Italian mag definitely came away with an artful—if unhealthful—cover. The next time Madonna had short hair was on her 1993 Girlie Show Tour. She's kept it long ever since, resorting to wigs for any looks that required a less-is-more approach to hair.


110 Cut 1 93 copyHypnotic/Hypnotic/Put your hands all over my body...


Cut (Japan, January 1993) by Steven Meisel

Madonna's flirtation with the '20s via Rolling Stone '91 (up a ways higher on this list) was too fun to go unused elsewhere. Rolling Stone wasn't going to put a black-and-white Madonna cover out there, but Japanese interview mag Cut had no such reservations.


Star Hits Dec 84 copyObviously not taken during her date with David Lee Roth!


Star Hits (February 1984) by Eric Watson

One of Madonna's first American cover stories was on this U.S. version of the British teen mag Smash Hits.

In the interview inside, the mag spills the beans that Madonna's next album would be called Like a Virgin and even correctly name-checks several tracks, months before it was finally released. Being a teen mag, Star Hits just hadda ask Madonna if she'd rather go on a date with Rick Springfield (b. August 23, 1949), Simon Lebon (b. October 27, 1958), Lionel Richie (b. June 20, 1949) or David Lee Roth (b. October 10, 1954):

“Ugh. UGH. Yeeeuch! C'mon. I wouldn't go out with any of them, if you want to know the truth. If I had to choose, I'd go out with David Lee Roth, but I wouldn't dress up for him.”

Most hilariously, when asked what she wouldn't wear in public, 1984 Madonna contradicts her near-future blank:

“Well, underpants. I wouldn't wear just sexy underpants in public.”

Her then-fave item of clothing was something she just so happened to be wearing on the cover— Vivienne Westwood (b. April 8, 1941) skirt with a Keith Haring design on it. She had worn the skirt in her “Borderline” video.


Eric Watson did this shoot with Madonna in 1983, and it went everywhere—everywhere! He was then one of the go-to photographers for Smash Hits (so his work was probably more readily available to the American sister publication) and a close associate of the magazine's assistant editor, Neil Tennant (b. July 10, 1954). Tennant, of course, formed Pet Shop Boys with Chris Lowe (b. October 4, 1959) shortly thereafter, and Watson became the duo's photographer and video director for a spell in the '80s. Sadly, Watson died of a heart attack at age 56.


109 Cahiers du Cinema 11 93 copyA different kind of drag queen


Cahiers du Cinéma (France, November 1993) by Lorey Sebastian

93_dangerous-game_001When Dangerous Game (née Snake Eyes) debuted to disastrous b.o. in 1993, Madonna was dubbed by at least one NYC tabloid the “Queen of the Bombs.” But forget the braying of the mainstream media about how the film was another piece of trash that proved Madonna shouldn't be acting—it's an interesting (if uncharming) film, and Madonna is not only good in it, she's great. As charismatic as she is in Desperately Seeking Susan (1985), as funny as she is in A League of Their Own (1992) and as moving as her performance is in Evita (1996)—her other great performances—Madonna's best acting to date is in this smugly unpleasant Abel Ferrara (b. July 19, 1951) film.

1993_dg07Nobody's putting a gun to your head, but you should check out Dangerous Game.

Along with it being a good, if insufferable, movie, it gave fans some fantastic images of Madonna looking chic and bored. The still used on Cahiers du Cinéma is one of the best.


107 Nuke 6 copy


Nuke (#6, 2008) by Maripol

Maripol was a close friend of Madonna's from before Madonna was MADONNA. She styled Madonna as the architect of the Boy Toy look that millions of teenage girls (and not a few teenage boys) would attempt to copy throughout 1983, 1984 and 1985, creating for Madonna an endless supply of rubber bracelets and industrial/punk bracelets, necklaces and pins that eventually led to Maripol preparing to launch an accessories line in 1985...which went south when Madonna changed her look unexpectedly.

While they were besties, Maripol took lots of intimate and striking Polaroids of Madonna, most of which were not published until decades after the fact. One of the most out-there would have to be this image of Madonna in a pink wig, which finally got its due almost 25 years on this special publication.


106 Schlager June July 1985 copyMotherpucker


Schlager (Germany, June/July 1985) by Deborah Feingold

The best thing about this over-the-top, sexed up Madonna cover might be the promise of a feature inside about a “SEXPLOSION!” that encompasses everything from Madonna to the 1984 camp-classic TV movie Lace!

The magazine's title translates to Hit in English, which both of those things definitely were.


105 Sunday Mirror Magazine 6 18 89 copyThe original barebacker


Sunday Mirror Magazine (UK, June 18, 1989 ) by Alberto Tolot

This magazine was inserted into regular editions of the British newspaper The Sunday Mirror, which made Madonna into quite a high-end Page 3 girl—“MADONNA NUDE”, it screams, and it doesn't lie...exactly. Still, while Madonna may be starkers, it's only on the cover and the photo is arranged so that you don't see any of the good stuff.

Was she ever hotter-looking than in her “Express Yourself” video? If so, when?


104 Video 11 85 copyShooting up, shooting up for your love...


Tele Cine Video (France, November 1985) by Steven Meisel

Goodness, gracious! Imagine if this image by Meisel from the Like a Virgin sessions had been that album's cover instead of the well-known Boy Toy bridal shot? I can't say this is Madonna's softest look, but that's why it's such a valuable and interesting (and rare) early cover.

Madonna-MeiselMadonna & Meisel in a degraded Polaroid from the LAV shoot

Looking Like a Heroin Addict, Madonna's gauntness is enhanced by the severe lighting. Even the colorized touches don't do much to soften this pic's edges. The image itself has never been a cover elsewhere, that I've seen.


103 Movie Scene Oct 85 copyIt really was the Madonna movie...


The Movie Scene (UK, October 1985) by Andy Schwartz

This quirky little movie magazine adventurously uses a candid of Madonna taken during the filming of Desperately Seeking Susan as its cover, which hit newsstands in the UK when the movie went into general release there. Well, maybe it wasn't adventurous so much as frugal—small publications don't have thousands of dollars for exclusive portraiture, so why not pay way less and make do with a perfectly nice photo of Madonna grinning?


Only problem they had to deal with, aside from how it would look blown up, was cropping out Rosanna Arquette (b. August 10, 1959), who was in the original on Madonna's right...which they almost accomplished (her shoulder got some love).

I've never seen a magazine that gives cover credit to its editor, but you go, Robin Bean (1938/39—February 2, 1992)!

Bean was actually a noted movie expert. He'd edited Films & Filming, Films and finally Movie Scene, the latter of which only existed for a year. The cover image was confirmed to me to be by Andy Schwartz, who shot the on-set DSS imagery.


102 Entertainment Weekly 5 17 91 copyMadonna the movie star


Entertainment Weekly (May 17, 1991) by Steven Meisel

This vulnerable pose from Meisel's session for Italian Vogue '91 (way further up this list) makes for a fetching cover, but gone are the days when EW could put one celeb on the cover and expect to Alek-Keshishianmove copies.

All the best images from the session appear inside this issue EW, including the controversial topless shot (though that one is postage stamp-sized), plus a lengthy profile regarding 1991's Truth or Dare [quote at right is from its director, Alek Keshishian (b. July 30, 1964)]. The profile contains numerous priceless quotes from Madonna's confidantes [Sandra Bernhard (b. June 6, 1955) bluntly says Madonna had bitten off more than she could chew but needed to do so to keep herself from being bored], but my favorite is from Herb Ritts, and it's because he provides a little insight into their first session:

“The first time I worked with her was when I was doing the poster for Desperately Seeking Susan. She marched in with this little cigar box full of jewels and trinkets that she wanted to wear. She knew exactly how she wanted to look. I liked that. She's very open to trying and doing.”

An even better, more elaborate story of Madonna's first meeting with Herb Ritts is here.

It's probably also worth repeating that Madonna issued a warning to potential critics of her movie, a warning that turned out to be much more generally applicable:

“If you take everything I do at face value, you're going to be horrified. Or intimidated. Or insulted. Or bored.”


101 Blitz jan 89 copyAll ears


Blitz (UK, January 1989) by Herb Ritts

This cuh-lassic shot of Madonna—who was, don't forget, called “Minnie Mouse on helium” in at least one unkind review early in her career—by Ritts was snapped while she was in Japan in 1986 and became a part of her Rolling Stone '86 (higher on this list) cover story.

For some odd reason, the image enjoyed a new life in 1989, making the cover of Blitz (which was writing about Ritts, not Maddy, as fans called her before that IMHO gross nickname Madge was born) and being used as the official single cover for “Dear Jessie” when it became a non-U.S. single.

If an image like this doesn't prove how much can be done with so little—a hotel room, a prop, a bed sheet for modesty—I don't know which one will.


100 Esquire aug 89 copyI would've zoomed in on Madonna and not used that hideous Roseanne Barr caricature, for starters!


Esquire (August 1989) by Alberto Tolot

Though I am not fond of the cover design here—so stark, so much unnecessary white space—the image of Madonna in her suit is fearsome.

The best part of this placement is that Madonna was, in 1989, the #1 woman beloved by Esquire's editors. I think now she would probably be on their list of loathed, not loved, women.

Inside, there is a delish Tolot shot of Madonna luxuriating in a bubble bath that harkens back to the Golden Age of Hollywood imagery.


99 ESQUIRE GER 11 89 copySuccess suits her


Esquire (Germany, November 2, 1989) by ? from an image by Alberto Tolot or from the “Express Yourself” video by David Fincher

Madonna-Esquire-1994Though I'm not sure who created this illustration, it's one of my favorite Madonna-in-art examples of all time. I gotta say that I prefer it to the less exciting cover the American edition of the mag used (see below), also of Madonna in her pinstriped suit.

Also more attractive than American Esquire '89 is Holland Esquire '94 (inset), which uses a black-and-white Tolot shot instead of recycling the Wayne Maser shot that was on American Esquire '94 (further up this list)—it's an artsy way to doll up what was by then an out-of-date (but timeless) photo.


DETAILS 1994_12 copyDetails, Details...


Details (December 1994) by Bettina Rheims

199412DetailsMadonna5of5Like Madonna herself, Details has gone through a number of incarnations. I remember it when it was a Downtown NYC party mag. Then it was kind of a general pop culture publication. It finally became a men's fashion bible with a glass-closeted slant toward gay men.

Madonna posed for Rheims during the general-interest era of the magazine. Their collaboration captured Madonna during her new jill swing period, showing her looking like a first-day-on-the-job crack whore in a tacky boudoir—or perhaps an hourly-rate hotel? Or a French bordello?

In the interview inside, Madonna is testy at a pattern in interviewer Chris Heath's questions:

“I feel like you're trying to be my psychiatrist. Maybe I should pay you when this is over.”

She didn't pay him when it was over. The cover story did little to tamp down any upset over Madonna's brazenly sexual, temperamental image.


97 Ad Lib 2 85 copyI love that this is from a time before Madonna knew how to blend her makeup.


Adlib (Japan, February 1985) by ?

For some reason, this Japanese magazine isn't as valued as I think it should be (although it usually changes hands for $100+), considering how very early it is in Madonna's covermag career, and how garishly charming the posed cover pic is. I mean, you can't get much more Boy Toy than this, folks.


96 Studio Voice 2 93 copySimply the breast


Studio Voice (Japan, February 1993) by Herb Ritts

Madonna-Herb-RittsThis high-end mag has the good taste to rescue a heretofore unused (as a cover), busty Ritts shot. Inside, the feature is extravagant, including an interview with Ritts and pieces on Madonna's greatest musical collaborators, such as Shep Pettibone (b. July 10, 1959), Nile Rodgers and Jellybean Benitez (b. November 7, 1957).

Along with a Warholian two-page spread, the issue offers around 80 different Madonna images, most prominently portraiture by Ritts and Helmut Newton, but many small shots by everyone from Steven Meisel to random paparazzi.


95 Elle France 7 2 90 New Time Hong Kong 6 8 87Back-to-back Madonna

#95 TIE!

New Time (Hong Kong, 1986) & Elle (France, July 2, 1990) both by Herb Ritts

This great shot of Madonna by Ritts was originally taken for Vanity Fair in 1986 (see the Top 10 of this list). Because it was already an old, second-rights shot in 1990, Elle's French edition can't be considered quite as big of a deal as a mag with an original shoot or with a very unique cover image—but it's still breathtaking, non?

I'm equally fond of the more timely use of this image on New Time (Hong Kong, 1986), which went with a more sepia presentation.


94 Pop spring summer 2002 copyStella!...Stella!


Pop (UK, Spring/Summer 2002) by Mert Alas & Marcus Piggot

Madonna's first encounter with Mert & Marcus led to this image of a woman who, 10 years after the Sex book, seems to be using her near-nudity casually, less defiantly, more comfortably. At this point, we were so used to seeing Madonna topless, that aspect of the cover hardly caused a stir. But at the same time, the stark quality did cause heads to turn, and played well with the magazine's bold declaration: “ICON”.

Madonna-Mert-MarcusThe retouching is rather aggressive, lending her a slightly reptile-goddess quality.

Inside, she looks mercilessly lean in Stella McCartney (b. September 13, 1971) and shows more nipple than Farrah Fawcett (February 2, 1947—June 25, 2009) in that red swimsuit from the '70s.


93 Vanity Fair 11 96 copyThe subscriber's edition, with limited cover text, is a work of art.


Vanity Fair (November 1996) by Mario Testino

Madonna is very fond of the work she's done with Mario Testino, and was so happy with this Vanity Fair cover story that she returned to him to shoot her career-redefining Ray of Light album cover. No doubt, Testino's take on Madonna as Eva Peron is quite strikingly different, and more vulnerable, than Meisel's (further up this list)—I imagine Madonna was pleased to have Evita's steely glamour as well as her humanity captured amidst all of that incredible wardrobe.

Oddly, Testino recorded Madonna's thoughts on the cover and released the tape:

Testino told the Telegraph in the UK of working with Madonna in 1997:

“At 2pm she said, 'OK, I’m tired. We’re done.' And I said, 'But I don’t have the pictures yet.' She said, 'You’re working for me and I say we’re done.' I said, 'No, we carry on.' The picture she used on the cover came after that. She didn’t intimidate me, you see. I thought, 'I have to push my luck here,' so I started kicking her like this, with my foot.  She was, like, 'Hey, what are you doing?' And I was, like, 'Move here, move here,' and suddenly this created an intimacy. When these people come across someone who treats them as an equal, it puts them at their ease.”

Madonna was the first non-model Testino shot. Next up? Princess Diana. After working with Madonna on a series of high-profile projects (including a Versace campaign), Testino became the fashion-photography powerhouse that he is today.


92 Paris Vogue Oct 93 copyMadonna was already having to say in 1993: “Shut up? I'm not ready.”


Vogue Paris (France, October 1993) by Ellen von Unwerth

MadonnaA female photographer for a change of pace! Relatively few women have shot Madonna over the years—and guess how many have shot her more than once?

Von Unwerth's images of Madonna for Vogue Paris are a change of pace for Madonna—they are far less about idealized glamour (Meisel) or idealized natural beauty (Ritts), instead providing a louche showgirl character for Madonna to inhabit. The spread is atmospheric and has depth and originality.

The black-and-white images, shot to help promote Madonna's short world tour The Girlie Show, were never used in or on any other magazine that I've encountered.


91 LA Style 3 89 copyShe had L.A. Style/She had L.A. grace...


L.A. Style (March 1989) by Herb Ritts

CherishOne of the prettiest portraits from Madonna's brunette Like a Prayer phase was this Ritts masterpiece. (It's reversed, but looks as good the other way, too!) A slightly different variation was used as the single cover for “Cherish” (among the last of her U.S. singles to be pressed as a 45), but I'm grateful for the more generous crop on this aspirational style mag, which was launched by L.A. Weekly and owned by AmEx before being sold and dissolved in 1993.

The magazine, which is oversized, is not easy to find today.

Madonna's work with Ritts litters this it should! Madonna has said of Ritts:

“What does it mean to get Herbified? It goes a little something like this: He talks you into going to the beach. Then, he talks you into taking off your clothes. He talks you into dancing and frolicking in the sand like an idiot. He talks you into getting into the freezing cold ocean, and before you know it, you have a sunburn and you’re freezing your ass off and you’re sure you’ve just made a huge fool out of yourself.”

An exhibition of Ritts's work in 2012 was also entitled “L.A. Style”.


90 Amica 1985 copyKen Regan thought Madonna was a hooker when he first saw her...


Amica (Italy, December 1985) by Ken Regan

This hard-to-find '85 relic is an oversized publication that sports a fabulous outtake from Ken Regan's People session on the cover.

But as people who aren't pretty are fond of saying: It's what's on the inside that counts. Part of what's inside this issue is a session of a drag queen emulating Madonna's Boy Toy look—they're not real, and they're spectacular!

Above, check out the late Regan recalling his special shoot with Madonna (which he thinks was only on 24 covers around the world, but I believe that number is way higher). Interestingly, he confirms that Madonna had requested him to do on-set shots of the film she directed in 2011, W.E.


89 Booklist 11 15 89 copyClownin' around


Booklist (November 15, 1989) by Matthew Rolston

Madonna-RolstonMadonna's only appearance on the official publication of the American Library Association came in 1989. It's not a substantial appearance inside-wise (certainly not compared to the magazine at #88 and others with original shoots), yet this usage of a Rolston image from 1986 makes for a very collectible and highly unusual cover.

As great as it is, it would've been extra-special had Booklist opted for the outtake above and left. just to change things up and to not do things quite the book.


88 Vogue 10 96My Peron and only!


Vogue (October 1996) by Steven Meisel

Madonna-EvitaPeople were actually rooting for Madonna in 1996—she'd crashed and burned in 1992, had regained some footing by 1995 and was about to give birth to her first child. She was the star of a seemingly quality film—Evita—in which she had landed the role she'd been born to play. And hey, the reviews were mostly pretty good, too!

For this, her greatest Evita-era cover, Madonna is delivered as a high-fashion icon in a spread of unforgettable Meisel images that are actually so style-driven you sort of forget about the photographer and the subject and even about the subject she's mimicking.

In a first-person piece inside, Madonna sums up her sartorial preferences:

“American designers don't inspire me that much. I can't really describe it, but do I look like a Donna Karan girl? I can appreciate some of them, but I don't wear any of them—oh, maybe bits and pieces of Marc Jacobs and Victor Alfaro. There's no J. Crew in my closet. No Gap. I don't own a pair of chinos or a pair of blue jeans. To me, the Japanese and European designers are closer to what I do as an artist, which is explore things, push the envelope.”

Less than 10 years later, she was strutting around with Missy Elliott (b. July 1, 1971) in her Gap denim!


87 American Film July August 87Madonna declares that Jamie Foley is “a genius“ in this issue.


American Film (July/August 1987) by Alberto Tolot

This cover was a nice placement for Madonna, who had done well with her first couple of mainstream movies (no one counts her pre-fame filmic abortion A Certain Sacrifice) then had stumbled badly with Shanghai Surprise (1986). With Who's That Girl (1987) coming, it made sense for her to try to be all over the then-numerous movie-themed publications out there. American Film (which published 1975—1992) was pretty mainstream, too, available in grocery and convenience stores and targeted at average-joe movie buffs in spite of being run by the prestigious AFI. It's a great picture that they use on the cover, showing a giddy Madonna—perfect to plug a screwball comedy.

But as we all know, Who's That Girl was a dud. More interesting to me in the candid interview inside is Madonna commenting on turning down Evita in 1987:

“I had several meetings with Robert Stigwood, and in China [while filming Shanghai Surprise] I read tons of literature on Evita, but Stigwood really insisted on doing an operetta kind of thing, and the only way that doing Evita would be interesting to me is as a drama, so it didn't work. I'd love to do a movie someday where I sing, but it's hard to make a transition if I do movies about singers.”

Oh, Madonna...

She also comments about turning down the 1987 Bruce Willis movie Blind Date [because he was in it—Lee Grant (b. October 31, 1925) would agree with her there!] and loving Mary Lambert's Siesta (also 1987) but not loving the required nudity. On the topic of nudity, Madonna was down with the flesh in Betty Blue (1986), but:

“I was disturbed by the nudity in Blue Velvet and felt it was done for the sake of shocking the audience.”

Heaven. For. Bid.


86 Cinema Ger 11 92 copy copySsssmokin'!


Cinema (Germany, November 1992) by Steven Meisel

You can read more of what I think about the image used on this cover at #11 on this list, but I think it speaks for itself, too, as a powerful—and powerfully aphrodisiacal—piece of work.

Published to coincide with Sex, this cover's image was actually shot at the end of 1990, but it fit with the theme like a love glove, so recycling it didn't lead to a dated-looking issue.


85 Globe Dec 90 Jan 91 copy


Globe (France, December 1990—January 1991) by Stephane Sednaoui

Madonna shares this cover, technically, with her then-squeeze Tony Ward (b. June 10, 1963). I love this about-to-kiss pic from her “Justify My Love” video, and the Globe logo is a chic part of why I also love this cover. It's got almost a hint of the '20s to it, but whatever the decade, it certainly it reeks of decadence.


84 Interviu 9 1 87 copySandy, can't you see?


Interviu (Spain, September 1, 1987) by Herb Ritts

Though all the rest of the images from Madonna's Virgin Tour packaging shoot with Herb Ritts in Hawaii look very high-class and arty and very woman-as-force-of-nature, I've always found this shot to be so incongruous with Madonna's image: She looks like any other dime-a-dozen disco dolly here, and she looks like she's wearing a bathing suit from Woolworth's.

Madonna by Herb Ritts 1985 (4)A more interesting variation, but not as commercial.

It was, in fact, so common that it was selected to be marketed as a poster, one of her first.

But its weird vibe—she almost looks like E.G. Daily (b. September 11, 1961—is why I live for the picture, and why I love it as a cover—even years after it was first shot.

Note: The image is reversed. Photo editors never really did their homework when it came to that beauty mark.


83 Movieline 9 12 86 copyIs Madonna forever blonde? So far, so good.


Cashbox (July 5, 1986), Movieline (September 12, 1986) & L.A. Weekly (November 10—16, 1989) by Herb Ritts

Gah, there are sooo many “Papa Don't Preach”-shoot covers to choose from for this list, but I've always found these three—which use different but very similar images in wildly different ways—to be equally outstanding.

First, I love Cashbox for using a full version of this Jean Seberg (November 13, 1938—August 30, 1979)-inspired Ritts portrait, and I think the handwritten cover line is a nice touch.

Madonna cashbox

Steve-MeyersI cherish the very rare Movieline cover and find it to be exceptional not only because of the scarcity of the magazine (it's from when Movieline was still a local publication, just a year into its existence) but also for the pop-art colorizing.

And finally, I think L.A. Weekly is not only even more fabulously pop art (and deliberately meant to mimick Andy Warhol's style), but the feature is a great summary of Madonna's status as a pop icon. I so loved the Steve Meyers (b. ?) illustrations used inside that I paid to reproduce them in my book, Encyclopedia Madonnica (1995)—donate to the Kickstarter if you'd like to see me do a sequel!

I kinda wish that one of Steve's drawings had been the cover of this publication instead—would've been even more fabulous.


Madonna-Rolling-Stone-1992-MeiselThat hooker is a looker!


Rolling Stone (June 13, 1991) by Steven Meisel

For Madonna's Truth or Dare-era Rolling Stone cover, she and her frequent collaborator Steven Meisel turned in a 1920s brothel spread, in which Madonna plays both a saucy chickadee who's on Madonna-Rolling-Stonethe menu and a sullen john who's sampling the fare. Most infamously, she drinks water from a glass held with her feet.

The interview is juicy, conducted by Carrie Fisher (b. October 21, 1956). At one point, Madonna identifies Dita Parlo (September 4, 1908—December 12, 1971) as a big inspiration and her namesake while staying incognito in hotels (we wouldn't hear more about her until Erotica arrived the following year) as well as Louise Brooks (November 14, 1906—August 8, 1985), both of them silent actresses. Asked who else she admires, Madonna says:

“Bette Davis. Oh, everybody I like is dead.” 

She goes on to say she's developing Martha Graham's (May 11, 1894—April 1, 1991) life story and wants to do Frida Kahlo's (July 6, 1907—July 13, 1954), in the process confirming that she will one day be a director.



81 Who 10 19 92 copyAs common as this image was in promo materials, it was uncommon on mag covers.


Who (Australia, October 19, 1992) by Steven Meisel

Madonna_sex_08This image of Madonna—with her head lolling back in languid pleasure—was used to promote her Sex book, particularly in a variation in which it is tinted blue. It was on the outside packaging of the Japanese version of Sex (which came in a cardboard box) and was also used on large placards hung in bookstores to announce the book's arrival.

Inside this issue of Who, the magazine highlights some of the book's racy poses, but—unlike Madonna—can't quite muster the balls to go all the way.


80 Us June 12 1989 copyGiving us the slip


Us (June 12, 1989) by Alberto Tolot

It's hard to believe, but it's been 25 years since this icy-hot pose showed up on newsstands. Madonna's “Express Yourself” video had debuted to great controversy, with some calling the homage to Fritz Lang's (December 5, 1890—August 2, 1972) Metropolis (1927) genius and others getting hung up on the gender-bending, the crotch-grabbing and the carefully photographed nudity.


79 Photo 11 92 copyThe magazine's seal is unbroken, Madonna's is not.


Photo (France, November 1992) by Steven Meisel

One of the most famous photos Meisel shot of Madonna for her Sex book—excuse me, *their* Sex book—seemed to be too risqué to adorn any magazine cover. But not in France! Photo gave this explicit shot the cover treatment (in a sealed edition) as part of its spotlighting of the most scandalous images from the work.

I have to wonder if the Madonna of 2014 would allow the very natural and normal folds of skin around her mid-section to show in a photo. Glad the Madonna of 1992 did—it's a memorable image, as is.


78 Stars May 85 copyI assume Eastwood fired his agent after taking third billing behind Madonna and Morris Day.


Stars (May 1985) by Harold Becker?

Stars was an in-school publication meant to engage students with topical stories on popstars, movie actors and famous athletes in order to quiz them after as a test of reading comprehension. As much Stars USA April 1986 preview 400of a taboo topic as Madonna has always been, it's a bit hard  to believe that she was on the cover of this publication at least three times—though I think the best, most interesting, cover is this one.


Sadly, I am unsure of the photographer of this shot, taken during her performance of “Crazy for You” for the movie Vision Quest (1984), directed by Harold Becker. I do not believe this was taken by Richard Corman (b. ?), who snapped Madonna during the shoot; it appears to be from the same series that resulted in her “Crazy for You” 7" single cover. Becker is as good as guess as any.


77 Musik Express Sounds Ger 4 85 copyIn bed with Madonna


Musik Express Sounds (Germany, April 1985) by Steven Meisel

This beauty almost can't be attributed to Steven Meisel—they clearly used his original image, but the airburshing (which is what it was 30 years ago, pre-Photoshop!) is so extensive that this almost constitutes a separate, derivative work.

Musik-express-sounds-germany-magazine-1985-[2]-1247-pThat headline: “THE BITCH”

However you classify it, it's hot!


76 Record March 1985 copyNever forget your rubbers!

#76 TIE

Record (March 1985) by Deborah Feingold & The Quiet Storm (Thailand, August 1985)

Record, in an early cover feature by a serious music mag was, naturally, skeptical of the pop tart's sudden rise to fame. The gimmick of the feature is to try to theorize why Madonna became successful, with theories ranging from her walking all over others to her possibly being—gulp!—kinda good.

In three out of the five images of Madonna used on/in the issue, she has something in her mouth, so I'm thinking one of the mag's theories is unspoken but implied.

The Quiet Storm 8 85 thai copyLooks like this was printed from a daguerreotype!

I couldn't choose between Record and The Quiet Storm, mainly because as classic as the former is, the latter is just such a rare magazine to possess. Plus, I love seeing how different magazines with the same cover images look thanks to design and, in this case, aging newsprint!


75 Bazaar 5 94 copyMadonna watched her step around Martha Graham.


Harper's Bazaar (May 1994) by Peter Lindbergh

Tumblr_m6cn14E8Ed1r90m4vo1_1280Though it could be argued that there isn't much of Madonna left in this image thanks to post-production, it's also a lovely portrait, something that looks like Man Ray (August 27, 1890—November 18, 1976). Madonna is paying tribute to Martha Graham in this photo feature.


The text is a first-person remembrance by Madonna of her first meeting with the late Graham, which occurred when Madonna was a lowly dance student breaking the rules by not being in her classroom on time. Of Graham, Madonna recalls:

“She stopped dead in her tracks to see who the violator was. I was paralyzed. She was part Norma Desmond in Sunset Boulevard. The rest of her was a cross between a Kabuki dancer and the nun I was obsessed with in the fifth grade, Sister Kathleen Thomas. In any case, I was overwhelmed, and all my plans to disarm her and win her over were swallowed up by my fear of a presence I'd never encountered before.”

Madonna ends the piece by encouraging Bazaar's readers to follow their inspirations in life, as she and Graham, presumably, both did.


74 Chat 7 27 91 copyNailing it!


Chat (UK, July 27, 1991) by Bert Stern

This charming cover would have been further up on the list had it not been released a solid six years after Bert Stern shot the image that decorates it. It's a supercool shot, though, carefree and cute.

Another terrific cover that's a couple of shots away from this one is Rockin' On (Japan, September 1986).

Check out Picture Week from December of '85 higher up on this list for more Stern dish.


73 taxudguos december 90 copyA little touched


Mailman (Greece, December 1990) by Stéphane Sednaoui

Madonna was at her sultriest in the Jean-Baptiste Mondino-directed video for her sizzling #1 hit “Justify My Love”, so it's no surprise that images taken during the shoot by Stéphane Sednaoui do not disappoint. Still, Sednaoui really went above and beyond with his work, which captured Madonna with genuine eroticism and style. He was rewarded with, among other assigments, the chance to direct Madonna's music video for “Fever” in 1993.

I've always been particularly into this portrait—Madonna looks so sculptural and so dialed into her video character's sexual odyssey. This rare, oversized Greek mag really gives the image room to breathe.

There are quite a few astonishingly beautiful Greek cover magazines to be found out there, and many are uncommon among collectors in the Americas—this is a prime example.


72 Video News Brazil 90 or 91 copyAre you fur real?


Video News (Brazil, November 1990) by Herb Ritts

Madonna received mixed but mostly positive reviews for her turn as “Breathless Mahoney,” the moll and—SPOILER ALERT—the villain in her lover Warren Beatty's big-budget comic-turned-movie Dick Tracy (1990).

72 Video News Brazil 90 or 91 copyFlipping out: Here's how she looks when she's not reversed.

I give two thumbs up to this rare cover from Brazil, which utilizes an uncommon Ritts portrait. Yes, the focus is set to The Doris Day Show-fuzzy, but it's still a knock-out...even if the image is reversed. 


Madonna-w-magazine29 copyCream of the crop


W (June 2006) by Steven Klein

Madonna-horseMadonna had previously appeared on and in W in a series of dozens of images, and her second appearance was even more winning.

Turning lemons into lemonade shortly after a fall from a horse left her injured, Madonna incorporated equine imagery into her Confessions Tour tour program and this set of images by Klein.

71 W Mag May 2006 Korea W June 2006 Italy Van Fair 8 10 06The same cover image decorates W Korea (Korea, June 2006 ) and Vanity Fair (Italy, August 10, 2006).

In 58 pages (!), Madonna gets naked, communes with horses, wears a harness and flaunts her taut jawline, all the while playing with a riding crop. Klein has at times gotten a bit pedestrian in his work with Madonna over the years—hey, they can't all be amazing—but here, Madonna appears to be inspired as well as looking way better than she had throughout the early 2000s.

Take a peek inside this issue of W here.


70 Hamptons July 4 1990 copyParting is such sweet sorrow.


Hamptons (July 4, 1990) by Francesco Scavullo

Scavullo's instantly unique shoot of his old muse Madonna for Cosmopolitan (May 1990) traveled a bit, with that issue's cover image (or close variations) popping up on select publications around the world.

However, this shot of Madonna in a different (and more out-there) outfit from the Cosmo cover feature didn't go anywhere but straight to Hamptons, which ran its second of two nearly-impossible-to-find Madonna covers, both July 4 issues, albeit five years apart. (The 1985 issue is somewhat higher on this list.)

These colors definitely work on Madonna, and I like how she is sort of floating into the shot, like all that descending-angel action from her 1989 “Like a Prayer” video.

I only tracked this one down for my collection within the past year!


69 USA Weekend 6 8 to 10 90 copyDon't ever tell her to stop.


USA Weekend (June 8—10, 1990) & RTR Countdown (New Zealand, August 1990) by Herb Ritts

This beauty shot of Madonna in character as “Breathless Mahoney” is one of the best ones to come out of Dick Tracy, so it's no surprise the film's studio, Touchstone, gave it to the massively distributed USA Weekend.

Dick Tracy, often thought of as a bomb today, finished the year of 1990 as one of its Top 10 films, scored 7 Oscar nominations [Madonna's winning performance of “Sooner or Later” preceded the song's win for songwriter Stephen Sondheim (b. March 22, 1930)] and inspired her hit album I'm Breathless: Songs from and Inspired by the Film Dick Tracy.

RTR Countdown 8 90NZ copyI wonder who won the trip to the Dick Tracy premiere?

I couldn't decide between USA Weekend and New Zealand's RTR Countdown, as they're almost the same shot and RTR Countdown is also (1) a wider crop and (2) hella hard to find.


68 People 3 11 85 copyElizabeth Tayor appeared as an inset on Madonna's next People cover, too!


People (March 11, 1985) by Ken Regan

Ken Regan's fabulous portaits of Madonna in her HEALTHY/SWIMMER tank make several appearances on this list, but this is the originating publication—People hired Regan to snap the shots for what would be its first cover story on Madonna. She was riding such a wave of notoriety, the cover only needed one her image to sell it:


For my taste, Madonna's closeup pucker is less dazzling that some of the other shots from the session, but they're all ravishing, and they were taken at the very height of Madonna's Boy Toy phase. (Regan also shot images of Madonna working out, all dolled up, that have been compared to famously incongruous images of 1950s Marilyn Monroe pumping iron, but this seems to be—for once, when it comes to Marilyn homages—a coincidence.)

Madonna-schoolIn the profile, Madonna addresses her already bad reputation as a girl who goes all the way (gasp!):

“I've been called a tramp, a harlot, a slut and the kind of girl that always ends up in the backseat of a car. If people can't get past that superficial level of what I'm about, fine.”

Hilariously, People also quotes a friend of Madonna's from her school days defending her by saying that Madonna:

“...came from a good moral family. She is nothing like what she portrays.”

Well, maybe not nothing like it.


67 Premiere June 1991 copyBed head


Premiere (France, June 1991) by Steven Meisel

The most famous image of Madonna from her Truth or Dare documentary is this look from her Vanity Fair (April 1991) shoot. She's actually wearing an outfit meant to emulate one worn by
Madonna-CannesMarilyn Monroe in Bus Stop (1956), and while Monroe is also closely associated with several images showing the icon stretched across a bed, I think this particular shot of Madonna looks like pure Madonna and doesn't really evoke Marilyn. Either way, it's forever attached to, all things considered, her most successful movie.

Madonna's appearance at Cannes that year was a sensation—making her way up the grand staircase toward her Truth or Dare screening (it was such a hot ticket and so packed that many attendees were turned away and the theater wound up sporting lots of empty seats), Madonna turned and opened the wrap she'd until then held closely around her, flashing the world in her Gaultier bullet bra-and-girdle set.

Thanks to Madonna's spotty film career, this is one of the few examples of a serious film-oriented publication giving her the cover treatment.


66 Rolling Stone France Jan 4 to 30 89 copy“That's just an accessory, Harry. There's a difference,” Madonna told ET in 2012 of her smoking poses.


Rolling Stone (France, January 4—30, 1989) by Steven Meisel

This issue of Rolling Stone makes use of an interview Madonna granted to the writer Harry Crews (June 7, 1935—March 28, 2012) that ran in Playboy. The rest of the interior is nothing special—old images to decorate a second-rights piece. The cover, however, is another matter.

Making use of an image Meisel had shot of Madonna five years earlier, the cover is an '80s gem, not only because the image is extremely uncommon on any cover, but also because of the jaunty colorization.

It's a winner, even if RS France probably goofed by running a cover so close to Like a Prayer, yet too far out to have any info on what would become such an important record to Madonna's career and to pop music in general.


65 Vogue Espana July 1990 copyRain(coat)...I feel it...


Vogue Espana (Spain, July 1990) by Helmut Newton

You'll find Vanity Fair (April 1990) much higher on this list—it's the publication in whose cover shoot this image originated. While I rank VF much higher than this issue of Spanish Vogue, I think it would be pretty easy to argue that this particular image is more beautiful, and every bit as iconic.

Madonna in Spain, July 29, 1990 (the voice = gone!)

What I love about Newton's image here is that it's not referential; this is Madonna: Superstar, not Madonna: Superstar (Paying Homage to So-and-So: Superstar). The incongruity of the see-through vinyl raincoat, the fabulous diamonds and Madonna's yellow-blonde hair make for a bit of a surreal pose. That there is some dude hanging out in the background contributes to my impression that this could pass for a lost Pedro Almodóvar (b. September 25, 1949) still.


64 Vogue Italia 11 92 copyNo hippie chick


Vogue Italia (Italy, November 1992) by Steven Meisel

In 1992, when Madonna was catching hell for having not enough clothes on her body, she paused to do this unique fashion spread for Vogue Italia, shot by her then-photog of choice, Mr. Meisel. At that point, Meisel had been shooting her off and on for a decade. 

MadonnaInside, the renowned fashion illustrator Thierry Perez (b. ?) contributes high-cheekboned sketches of Madonna in '60s gear and also of various Madonna incarnations from her recent past—A League of Their Own, “Erotica” video, Sex book, Blond Ambition and more.

Parisian Perez, BTW, is the guy who did that stunning Sex party invitation illo that is arguably the best example of Madonna-in-art we're ever going to see (at left).

Tumblr_mmkj0rxEsN1sp5mf4o1_500Her name is, for real, her name really is Dita.

The mag also generously offers details on Dita Parlo, the woman whose name Madonna took for her Sex-era character, and a list of famous people affiliated with Madonna.

It's got a lot of bang for your buck, this smashing issue. It's findable on eBay if you're not counting your lire.


63Such a beach!


Rolling Stone (September 10, 1989) by Herb Ritts

The rock 'n' roll paper of record sure knows a good thing when it sees one. How else to explain the fact that Madonna got the cover twice in the space of about six months in 1989?

After her Like a Prayer cover story with an image by Ritts (elsewhere on this list), she was back with this carefree beach shot (also by Ritts) to illustrate the magazine's special photo-album issue. It's easily identifiable as having been taken on the set of her “Cherish” video, the first music video Ritts ever directed. [He would go on to direct videos for Janet (b. May 16, 1966) and Michael Jackson (August 29, 1958—June 25, 2009), Chris Isaak (b. June 26, 1956), Jennifer Lopez (b. July 24, 1969), Britney Spears (b. December 2, 1981) and others before his untimely death.]

Inside was an image of Madonna photographing Ritts as he photographed her.


62 Air Check 6 13 1987 copyServing you bolero jacket Mitsubishi realness


Air Check (Japan, June, 13, 1987) by Herb Ritts

I love any Mitsubishi imagery, and this unique cover by Ritts (almost) takes the cake. I've never seen it used as a cover anywhere else, it's a great action pic and the magazine is itself hard to find.

Madonna's ads for Mitsubishi in Japan became legendary among non-Japanese fans; it was hard for us to find the images, let alone see the commercials, since there was no easy way to view them on our VCRs even if we could locate a Japanese citizen willing to send us tapes, and the whole point of doing commercials overseas is to take the paycheck and do everything in your power to make sure the audience Stateside never sees them.


 I could watch these things all day, even in this shitty quality.


61 Switch Oct 86  copyWhen a man loves a woman? But the devil is a woman...


Switch (Japan, October 1986) by Matthew Rolston

Japan's Switch Magazine is one hell of a posh publication. It spares no expense, and has great taste in covers—always. Switch has had more than one eye-popping Madonna cover, and this is definitely a stand-out—a Rolston image that had just been seen earlier in '86 inside Rolling Stone (found higher on this same list).

Incidentally, the quote on the mirror comes from the 1930 Josef von Sternberg (May 29, 1894—December 22, 1969) film Morocco, in which Marlene Dietrich and Gary Cooper (May 7, 1901—May 13, 1961) fall for each other—hard. It's the film in which Dietrich performs in a tux and kisses a dame, a look Madonna mimicked in 2013 to great effect.

Rolston first shot Madonna this same year, 1986, but would later direct her “The Power of Good-Bye” video. His first shoot with Madonna was haunted by Dietrich, but his music video with her was haunted by Joan Crawford (March 23, 1904—May 10, 1977) in Humoresque (1946).


60 Starlet Sweden 1985 copyIt's Madonna time!


Starlet (Sweden, 1985) by Gary Heery

This rare teen mag became a hot commodity among global Madonna collectors only after the advent Madonnaof eBay revealed that it existed! I certainly had not seen it in the '80s or even the '90s. I love it because of its bold name and the unique, never-used-elsewhere cover image by Heery, taken from the shoot used for her first album cover.

Those images were taken in 1982 and this magazine was released three years later, but the power of an unseen image is something all magazine editors know. A variation, with the same glasses and with the addition of a cap, is seen at left, above.


59 Photo Mar 91 NY Post 5 3 91One man's tramp is another man's treasure.

#59 TIE!

Photo (France, March 1991) & New York Post (Friday, May 3, 1991) by Jean-Baptiste Mondino

I couldn't choose between these two variations of the iconic Madonna-as-Marlon-Brando (April 3, 1924—July 1, 2004) image by Mondino, a shot that graced Madonna's “Justify My Love” single, because each is important and effective in its own way.

Photo came out first, and beautifully frames the work with simple, black-and-red text for its special issue devoted to rockstar portraiture.

But the godawful New York Post gets points for coming up with so laughable and hyperbolic a headline that the cover became a popular bootlegged T-shirt for years afterward. Fans were reclaiming the tramp stamp in the same way Madonna always has.

It's actually a peculiar image for the paper to have used in that it doesn't exactly telegraph sluttiness, as so many other Truth or Dare hand-out photos do.

Oddly, the Post's hack writer Kerrison (b. ?)—described in the paper's 2012 obit for his wife as “being best known for his insightful coverage of horse racing”!—felt Madonna's schtick was to “amuse the jaded,” and castigated her for speaking to The Advocate (the cover of which makes my Top 10 on this list), cattily noting:

“She has given a two-part interview, appropriately, to a homosexual magazine...”

What a tramp? What a homophobe.

Kerrison's right-wing rage against Madonna has been replaced by Andrea Peyser's (b. ?) right-wing rage at the Post; Peyser has ripped Madonna a new one more than once over the years. Peyser also loathes President Obama (b. August 4, 1961) and Christiane Amanpour (b. January 12, 1958), so at least Madonna is in good company.

Shockingly, the Post recently ran an article defending Madonna's cougar status. The Post, it is a changin'.


58 New Woman 1 92 copyLove how unretouched this is—the flesh-colored material that makes her look  nude in other versions is clearly visible.


New Woman (Australia, January 1992) by Steven Meisel

Though the images were published widely in 1991, this shoot with Meisel turned out to be the gift that kept on giving. This absolutely terrific shot turned up on this Aussie women's mag at the beginning of 1992, many months before still other shots from the session would be repurposed to promote Madonna's Sex book.

When was the last time a magazine proposed to tell us why we should all be more like Madonna? Oh, about January of 1992.

Unfortunately, the piece is by ridiculous, pseudo-liberal, anti-feminist Camille Paglia (b. April 2, 1947), so it's a lot of balderdash. But the cover is gold.


57 Panorama Spain 7 30 90 copyVote Pedro!


Panorama (Spain, July 30, 1990) by Juan Jose Gonzalez

Oh, how I love this magazine!

Madonna-AlmodovarThe cover is a random candid by events photographer Gonzalez, but it's worthy of my affection because it's unique, it captures a moment in time, Madonna looks as beautiful as she ever has and it's even got a very young Almodóvar thrown in for good measure!

This weekly or biweekly newsmag coughs up no fewer than 13 then-fresh, still-unique images of Madonna and her camp yukking it up with Almodovar and his camp, including a shot of Madonna and Almodovar actor Antonio Banderas (b. August 10, 1960)—pre-U.S. fame, before he would become her silver-screen “Che”—joined at the hip. Except, you know, they're joined at the front part of the hip. Oops. Did the wife miss that photo? Banderas seriously looks like he is giving Madonna a feel of that which she allegedly, as seen a year later in the Truth or Dare footage from this night, could not have.

Seeing Madonna with Almodovar's most famous stars really sickens me to this day that she never somehow did a movie with him. She could have fit right in as some sort of wacky American actress walking around reading her lines in Spanish and taking lovers of both genders.

Almodovar-MadonnaMadonnAlmodovar: Through the years

My only complaint about this treasure is that they chose that photo as the cover...if you see the others inside, there are several that would've worked even better.


56 IL MONELLO 4 18 86 copyMesh you like crazy


Il Monello (Italy, April 18, 1986) by Fryderyk Gabowicz

This rare issue of an Italian magazine that had Madonna on the cover multiple times contains a startlingly unique early image that sums up her Boy Toy look succinctly. That black mesh tank sure got a lot of use in her early track-date days.

Madonna-GabowiczAnother shot from the Gabowicz session

Inside is a two-page piece on Madonna's rising star. The article is a lot more current than the photo, which while unusual and stunning was older (1984) by the time it appeared here.

Gabowicz shot countless images of rock and pop acts on promo tours in Germany, servicing teen (Bravo) and other magazines for decades. Some have said this image is actually by Gunter W. Kienitz...I'm open to input!


Madonna-Venice-June-1991Via eBay: Right back atcha!


Venice (June 1991) by Steven Meisel

One of Madonna's hottest promo shots for Truth or Dare was this topless snap from behind, which gives us a crack at understanding that Madonna meant for the film to provide ALL ACCESS. It's actually a pretty simple photo—even the handwriting on Madonna's back appears to have been done quickly (and off-center). But it's a great shot nonetheless, and one that does not appear—unlike quite a few others from this period—to have been an homage to a previously existing star or image.

55 Lui 4 92 copySpines like us

My copy of Venice eluded me in my search, so I'm also providing a scan of Lui (France, April 1992) from the following year.


54 Us June 13 191 copyGreat quote from the annals of no-shit


Us (June 13, 1991) by Steven Meisel

This pre-pucker shot from Madonna's Truth or Dare promo session with Meisel looks downright demure when cropped, but had Us run the whole enchilada on the cover, it's hard to believe Walmart would have swallowed the semi-taco she was presenting:

In this staple of any Madonna fan's collection, the interviewer speaks to Madonna for what reads like hours. It's unimaginable today that any article in Us would run even 1/12 as long as this one. Choice quote comes when Madonna is asked if her fellating a bottle in Truth or Dare is shocking:

“My giving head to a bottle? Why? You see people doing it in movies all the time. It's a joke. What's shocking? Why don't you know if it's shocking or not? Don't you know your own feeling? It's a joke! The idea of Truth or Dare is a joke. It's like all those childhood games; 'I dare you to do this.' It's all a game. If everybody put on film what they did in those games when they were children, or what they did in their fraternity games, I mean, my God, they'd all be arrested.”

Well, that's true when it comes to Madonna's childhood games—just ask Moira. If she doesn't lie!


63 Rolling Stone 5 9 85 copyPlenty of pearls of wisdom inside


Rolling Stone (May 9, 1985) by Herb Ritts

Madonna doesn't always blend well in dual shoots, but her chemistry with Desperately Seeking Susan co-star Rosanna Arquette is a perfect microcosm of their characters' relationship in the classic (yes, classic—it's an '80s masterpiece) film: Madonna as sex bomb, Rosanna as pretty but tentative doppelganger.


Madonna-RS_RittsThe cover features one of Madonna's patented just-put-your-jewelry-in-your-teeth poses, and the other two-shot inside presents the women in a neat, retro floral motif. Madonna poses in Hawaii in a series of beach-fashion looks for Ritts, surrounded by a bevy of surfer boy toys.

The feature details the making of DSS, including a candid admission from Arquette:

“Madonna laughs off bad press, but I still get hurt.”

No doubt it later smarted when the press (and Orion) called DSS “The Madonna Movie,” but hopefully she got over it—Arquette's performance is the heart and soul of the film, even if it's Madonna who makes it cool. And both ladies bring the requisite laughs and sex appeal.

From the Encyclopedia Madonnica vault: I own several original test Polaroids from Ritts's shoot with Madonna and Rosanna. They're among the handful of things I would rescue in a fire, right after my dogs and right before my cellphone.


52 Playboy Japan 12 87 copyGiving us the bold shoulder


Playboy (Japan, December 1986)

OMG. I think my soul fluttered out of my dead body like in those old “Bugs Bunny” cartoons the first time I laid eyes on this Japanese Playboy cover in Charles Criscuolo's (b. ?) Flashback shop in Chicago in 1987 or 1988. I bought it instantly for I think $40 or so.

Madonna-Yes-BeautifulM&M: Madonna & Mitsubishi

Inside, the images are mostly familiar shots from 1985 and 1986, but the magazine's back cover is a dazzling Mitsubishi ad—and I'm a lifelong sucker for absolutely anything relating to Madonna's bleached-blonde, blingy Mitsubishi looks in any form. They're nice images and some of them were exclusive to Japan. The ones in this ad have popped up elsewhere, but it's still a beautiful ad. Yes! Beautiful.


51 Bazaar Ger 1 87 copyErotik, erotik...


Harper's Bazaar (Germany, January 1987) by Alberto Tolot

Madonna-TolotTolot's glamour shoot with Madonna in 1986 was recycled many times over, but one of the most desirable covers that resulted was this classy Bazaar edition from Germany. It's almost impossible to track down now.

Madonna's expression is utterly blank, inviting any interpretation you'd care to bring, rather like a facial mood ring.

Inside, the magazine generously offers 16 shots from the session, a rarity—magazines pay up the wazoo for each image they use, particularly approved portraiture such as these. It's a bit jarring to see Madonna in a white fur vs. Madonna Mickey Mousing around, but it was invaluable at the time (pre-scanning, pre-Internet) to have so much of Tolot's shoot in one place.


50 Esquire 8 94 copyPopstarget


Esquire (August 1994) by Wayne Maser

When Madonna crashed and burned after littering a hostile appearance on David Letterman's (b. April 12, 1947) show with multiple F-bombs (an appearance that would later come to seem hilarious to some fans, even though it made America hate her at the time) and a drug reference, she became Public Enemy #1. Mailer-MonroeThat's why this Esquire cover story was such a wise move and so visually clever—it's a sexy image that plays off of Madonna's then-recent Sex book provocations and that puts her on a target to immediately communicate the situation in which she found herself in 1994, and the story is an imaginative coup—her first encounter with Norman Mailer (January 31, 1923—November 10, 2007).

Mailer had famously written of Marilyn Monroe, a human being, an actress, an icon...and a recurring theme that runs throughout Madonna's career. Having him quiz her at this juncture of her life was genius.

1994-madonna-esquire-04Mailer's interview (he didn't write the introductory piece) is unhinged and cranky. He openly tells Madonna why he disliked her Sex book:

“Once you have to compromise an idea, maybe it’s better to do without it. I thought you were going to say, as you did in Sex, 'I’m not interested in porno movies because everybody is ugly and faking it and it’s just silly,' and yet you were going to attempt to shock people, then you should have had a beaver shot yourself. Given the number of nude and seminude pictures of you in costume, I thought that was an evasion, as if you or your advisers were saying, 'Beaver shots could hurt us commercially. What we want is soft porn.' So, the fact that Sex was designedly commercial got a lot of people’s backs up. They felt you were promoting yourself without large enough commitment. This sets up a dismissal of the reader.”

Yes, because the reason Madonna was crucified over her Sex book was the lack of beaver shots.

Mailer also goes on a tirade against condoms, even if they helped to stop the spread of HIV. It was 1994!


49 Rolling Stone March 23 1989 copyBrown/derby


Rolling Stone (March 23, 1989) by Herb Ritts

Madonna-potWhat a breath of fresh air it was when Madonna washed that blonde right out of her hair and presented herself as the brunette Michigan girl she'd been born and had always been underneath the glitz and the look-at-my-tits. Herb Ritts perfectly captures Madonna's desire to be seen as a singer-songwriter, not just a provocateur, in this famous RS cover.

Of course, she almost immediately scandalized the world with her controversial “Like a Prayer” video, and then dyed her hair blonde again.

Speaking to Bill Zehme (b. ?) inside, Madonna earned some bitterness from La Toya Jackson (b. May 26, 1956) by allowing herself to be quoted snarking on the latter's “major tit job” in Playboy.

But she also comments on what turned out to be her crumbling marriage to Sean Penn by way of commenting on her song “Till Death Do Us Part”:

“I wanted the song to be very shocking, and I think it was. It's about a dysfunctional relationship, a sadomasochistic relationship that can't end. Now that's where the truth stops, because I would never want to continue a terrible relationship forever and ever and ever until I die.”

And she didn't!


48 Paris Vogue Klein 2004Hair apparent


Paris Vogue (France, August 2004) by Steven Klein

Paris-Vogue-MadonnaMy highest-ranking Klein cover is the magazine with this closeup, one which confidently obscures nearly all of Madonna's face, and yet is still unmistakably her.

Inside, Klein's hallucinogenic images show Madonna prepping her Re-Invention Tour, including a portrait of Mama Madonna holding her toddler-aged son Rocco (b. August 11, 2000).

It's a unique layout, and in total represents one reason by Klein has become—in the absence of Herb Ritts—one of Madonna's go-to shooters.


47 Entertainment Weekly Nov 6 92 copyHow far am I goin'??? All the way!


Entertainment Weekly (November 6, 1992) by Steven Meisel

The best image from Madonna's Sex book with Steven Meisel—of the star hitchhiking nude—somehow found its way onto the cover of a magazine that needed to be stocked on all the check-out Marilynstands of every grocery store in Middle America. EW had solved the problem of the nudity by dressing Madonna with a big, bold question mark. It's a brilliant design work-around.

Outrageously, this photograph was once mistaken for being a long-lost image of Marilyn Monroe! (Check out a young MM hitching at left.) A man found a print of it in a storage unit and a Marilyn Monroe expert authenticated it as being of Monroe. Just before it was unveiled on a morning news show, reporters from Associated Press viewing it were quickly able to ID it as Madonna. There is nothing in the image to suggest that it is 2001-EWof Marilyn Monroe or that it could possibly have been taken in the early '60s, so I'm pretty sure that Monroe expert's phone hasn't rung much since.

After the Sex era, EW turned on Madonna, even declaring her career over in 1994 after she admittedly made a fool of herself with David Letterman. She only had one more cover from the magazine—which says a lot considering it was a fellow Time-Warner holding and needed to fill 50+ covers a year!—after 1992, an acknowledgment of the big deal it was in 2001 when Madonna finally returned to touring after an eight-year hiatus.


46 Max German 8 91 copyThe nipple effect


Max (Germany, August 1991) by Steven Meisel

French-Max-MadonnaMeisel's Marilyn Monroe shots of Madonna from Vogue Italia (February 1991) didn't reveal this exact hot shot. French Max (June 1991—pictured at left) had an almost identical cover, but cropped it just before the nipple.

To this day, this cover jumps out at me as both a work of art and Playboy-ready. 

The issue itself is a must-have for Madonna fanatics, packed with 22 pages (!) of Madonna images, many of them full-bleed.

As you read this list, you'll probably discern that I have a bias toward Madonna's 1989—1991 era. I just think this is when she was making the strongest visual statements and looking the most bewitching. Am I wrong?


45 Rolling Stone June 5 1986 copyI keep my copy between a painting by Phyllis Diller (July 17, 1917—August 20, 2012) and a photographic work by Slava Mogutin (b. April 12, 1974).


Rolling Stone (June 5, 1986) by Matthew Rolston

The first time Madonna went through a radical image and look overhaul was in 1986, when the “Papa Don't Preach” video came out. Sure, the “Live to Tell” video threw some of us for a loop, but Madonna looked like she was playing a period character or something. But in “PDP,” it was like a whole new Madonna—slim, sleek, short-haired, classic.

Rolling Stone was the magazine that got to introduce us, photographically, to this new creature, who would be further rammed down our throats via the True Blue album cover by Herb Ritts. But for the magazine, Matthew Rolston was our “Henry Higgins,” giving us a demure wallflower (wellllll...she is up against a wall and she does have a flower in her cleavage) version of the woman who not long before had been caked with makeup and layers of flashy, trashy, Downtown-chic glad rags.


Inside, the images could not be less like the Madonna of yesteryear: She poses a la Marlene Dietrich in front of a mirror and as a circus ballerina next to a clown.

In the interview by Fred Schruers, Madonna articulates the difference between an actor and a singer:

“When you're an actor, you do your work and you go home, and people deal with what's up on the screen. When you're a singer, obviously it's you. That's what the music is all about. It's a lot more accessible. You're saying, 'This is me,' so people know you intimately.”

Interesting to keep in mind while listening to “Gang Bang” (2012).


44 Paris-Match-9 4 87 Max Marzo 87Get up, stand tall/Put your back up against the wall...

#44 TIE!

Paris Match (September 4, 1987) & Max (Italy, March 1987) by Herb Ritts

Throughout this list, I am giving alternate examples of magazines using the same image. However, in this case as in several other cases, I'm not just using these two as separate samples, I'm declaring them equally amazing and worthy of being ranked.

RIchard-MisrachThe reason I love Paris Match is that it has the original, black-and-white, unadorned Ritts portrait (which looked great on a Who's That Girl official concert tee, too, BTW). I'm not the only one who loved it—artist Richard Misrach (b. July 11, 1949) shot Ritts's image with bullet holes through it, called it Playboy #92, and created a separate work—prints of which now sell for thousands. (His The Playboys series is a set of images showing old issues of Playboy Magazine that had been shot up for target practice on a military base.)

The reason I love Max is that it's still a stark, beautiful image, but it has that Warholian, heavy-handed colorizing. It's also a large-format magazine and is extremely hard to find. It came first, so it would hardly seem fair to rank it above/instead of Paris Match.


43 King Moda 6 87 copyDress her up in true blue


King Moda (Italy, June 1987) by Herb Ritts

This gigantic mag set me back 15 bucks when I was in college and surviving on 50 bucks a week, literally. But it was worth it. It's almost 12" wide and 16" tall, so it's a big'un. And that cover photo by Herb Ritts—and I know I'm cheating a bit because it's very similar to Vanity Fair (December 1986), which you'll find higher up on this list—is divine.

White hair, ice-blue gown, cocked head. It makes for a grand display.


42 Interview 2010 copyDon't ever try to cross her.

#42 TIE!

Interview (May 2010) by Mert Alas & Marcus Piggott, both versions

Marilyn-Monroe-Bert-SternIt may seem impulsive to rank a relatively recent cover so close to the Top 40 of all time, but it's been four years (!) already and damned if this cover by Mert & Marcus isn't a glorious return to form that merges several important elements of what makes a memorable Madonna cover: The gorgeous eyes, the Boy Toy styling (Maripol, your influence lives on!), high drama and even a subtle reference to Marilyn Monroe's Bert Stern session via the cross (see image above at left)—which also harkens back to Madonna's previous obsession with Catholicism.

In short, it's perfect...and best of all, it's twins: There were two, slightly different covers released.

Madonna_interviewmagazine2010_5 copyIn the equally perfect interview, Madonna speaks with filmmaker Gus Van Sant (b. July 24, 1952), whose film Good Will Hunting she once told an interviewer was her favorite of 1997. It's a Q&A  in which she responds to a question about Van Sant's 2008 film Milk with a long response regarding her own past experiences with gay men:

“I did when I was younger. But you know, what the movie triggered for me was all my early days in New York and the scene that I came up in-you know, with Andy Warhol and Keith Haring and Jean-Michel Basquiat and Kenny Scharf. It was just so alive with art and politics and this wonderful spirit. So many of those people are dead now. I think that's one of the reasons I cried. In fact, the character that Richard E. Grant plays in the film I directed, Filth and Wisdom [2008], is this blind professor who was based on my ballet teacher, Christopher Flynn. Growing up in Michigan, I didn't really know what a gay man was. He was the first man-the first human being-who made me feel good about myself and special. He was the Madgefirst person who told me that I was beautiful or that I had something to offer the world, and he encouraged me to believe in my dreams, to go to New York. He was such an important person in my life. He died of
AIDS, but he went blind toward the end of his life. He was such a lover of art, classical music, literature, opera. You know, I grew up in the Midwest, and it was really because of him that I was exposed to so many of those things. He brought me to my first gay club-it was this club in Detroit. I always felt like I was a freak when I was growing up and that there was something wrong with me because I couldn't fit in anywhere. But when he took me to that club, he brought me to a place where I finally felt at home.”

Whtbj laugh

It doesn't get much better than this. And here is as good a place as any to say: Fuck anyone who compares Madonna in her fifties (she was 52 here) to characters/caricatures like “Baby Jane Hudson” or “Norma Desmond.” “Baby Jane” never had beauty or talent or success as an adult, which can't be said of Madonna by any serious person.


“Desmond” was at least a character who had beauty and talent and success, but one who failed to realize her age made her undesirable to a youth-obsessed world. Madonna in her fifties remains a lovely and more importantly an intellectually engaged artist, someone with a clear-eyed view of herself and only rarely given to the flaw that every famous person possesses—that detachment from everyday normalcy that leads her to occasionally pontificate. And she's still filling arenas. No one is asking, “Who was Madonna?”


It's not Madonna who is deluded about who she is and what she has to offer; it's her detractors who are suffering from a derangement brought on by the fact that Madonna, whom they're welcome to find annoying or shallow or amoral, is still a major force. She's more current and relevant than any other popstar of her age ever (you should pardon the expression) has been. And she's not done yet.


But just for the sake of OMG!!!, Madonna is older than Bette Davis (April 5, 1908—October 6, 1989) or Gloria Swanson (March 27, 1899—April 4, 1983) were when they played those characters. She's also older than Rue McClanahan (February 21, 1943—June 3, 2010) was when Golden Girls (1985—1992) first aired.


41 Cosmo July 87 Japan Aug 87I slightly prefer the Japanese version, in which Madonna's wrinkles survive.

#41 TIE!

Cosmopolitan (July 1987) & Cosmopolitan (Japan, August 1987) both by Francesco Scavullo

1984 scavullo (2)Madonna had posed for Scavullo earlier (pictured at left), in one of her best-ever, most out-there shoots—which consisted of wild, gelled hair, dragon jewelry and heavy makeup—so was certainly familiar with him by the time she came for her 1987 shoot, which resulted in her first cover for the important fashion mag.

In the Chris Chase (January 12, 1924—October 31, 2013) interview, Madonna reveals of her ups and downs with the media and her then-hubby, Sean Penn:

“I've been dealing with the media since the very beginning of my career, and Sean never really had to. I wanted it, and I was sort of ready to deal with it, and he wasn't.”

The piece is flagged with a stop-the-presses announcement that Madonna had filed for divorce from whom she would eventually stay married until 1989.

Dig through the rest of the issue here.


40 Newsweek 11 2 92 copyGolden girl


Newsweek (November 2, 1992) by Wayne Maser

You will not find a magazine more recent than 1992 in my Top 40. This is not because there are no good—even great—Madonna covers in the past 22 years, it's simply because the power of the older covers has had a longer time to seep in. I would hate to toss a hot, new cover (like 2014's squeal-inducing V, for example) way up on the list and deprive a more time-tested winner its recognition.

I think the best cover from Madonna's Sex era, which was marked by quite a few covers that were simply outtakes or shots lifted directly from the book, is this cynical Newsweek cover, which uses an image of Madonna to tackle the larger issue of the marketing of voyeurism. Her first flirtation with a gold tooth wasn't actually very much more attractive than her 2014 re-flirtation via a gold grill, but you'd be hard-pressed to prove that in this striking image, which is a work of art.

Madonna-goldMadonna goes for the gold in 1992 and 22 years later.

Inside, in an interview with David Ansen (b. ?)—who also spoke to her for Cosmo's May 1990 issue—Madonna compares herself to Robert De Niro (b. August 17, 1943) when asked what she'll do to top herself, and complains:

“It's just that the arena that I choose to express myself in is sexuality, and sexuality has always been a taboo subject. But I'm trying to change that. When people say, 'What are you going to do next?' I just laugh, because I'm just going to do what I do, and I'm going to keep doing it.”

And she did.


39 Amica Italy 87 copyLeather & face


Amica (Italy, August 17, 1987) by Alberto Tolot

I love this oversized cover from Italy, which uses a rarely-seen shot by Alberto Tolot. During this same session, Madonna cavorts with a Mickey Mouse doll and sports a tiny li'l cap, but this leaping, leather-skirted variation is the one for me. I like my Madonna clothing my men.

Madonna-Mickey-MouseSlipping her some Mickey

Taken right around the time of her “True Blue” non-U.S. music video shoot, this shows off Madonna at the height of her short platinum look. The issue is next to impossible to snag today, but don't give up—it took me over 20 years after its release to find my copy.


38 LIke a Fanzine fall 1990 copy“Breathless” with anticipation!


Like a Fanzine (Fall 1990) by Herb Ritts

Like-a-Fanzine-Marcia-DelVecchioWhen Madonna finally got an official fanzine up and running, her people didn't mess around—the publication, initially named Like a Fanzine but renamed Icon by issue #3, was a slickly produced color affair that almost always featured new-to-us images of Madonna. So prized was this 'zine that early issues regularly sell for hundreds of dollars today—when you can find them.

It's a testament to the late editor-in-chief Marcia DelVecchio (?—June 1999) and her husband Rob (b. ?), who worked on the magazine together with support and materials provided by Liz “The Validator” Rosenberg (if you think I'm giving away Liz's birthdate, you're crazy), that a complete set of Icons is must-have for any serious Madonna collector.

I was totally plugged in to the Madonna-fan scene back in 1990 (which means I had a lot of pen pals and free postage from work—god damn that Internet would've helped!), so I heard about the new fan club in time to subscribe and get the debut issue with this absolutely (and literally...didja see the movie?) killer “Breathless Mahoney” shot.


37 Max 8 89 copyBedtime story


Max (France, August 1989) by Alberto Tolot

One of the most lavish treatments of Madonna's Like a Prayer era came in this French treat, a sumptuously produced magazine with a 16-page feature, double-sided poster (one of the sides shows Madonna's ass through her sheer “Express Yourself” video garment) and generous amounts of “Express Yourself” stills.

Madonna-Express-Yourself“Express” way to your heart

Just a few months after being all earth mommy brunette, Madonna wasn't able to resist going platinum again...but always remember that she crawled under her own chair in that video, guys, and lapped up her own milk from a bowl like a cat. Like, no man made her do it.

I used to supplement my nearly nonexistent salary by buying foreign Madonna covers and re-selling them to fans who lived nowhere near metropolitan newsstands. If I'm remembering correctly, this was the first cover I bought in bulk for which I was able to get the then-princessly sum of $30 a pop!


36 u 90 copyGiving good face


U (1990) by Lorraine Day

This unique artzine was published for a short period of time in Michigan. Madonna graced its second-ever cover. The photo is a great still from the “Vogue” video by Lorraine Day, though the lengthy feature inside is dominated by Herb Ritts shots from Vanity Fair (December 1986). It also contains three more classic Day stills from “Vogue” and an exclusive interview with choreographer Vincent Paterson (b. August 24, 1959) about the making of that video and of Madonna's Blond Ambition Tour.

Paterson says:

“(Madonna) is like a little girl. That's the beauty of her and that's the reason I love working with her. She's not afraid to make statements. She's not afraid to make comments on political situations, or 108 Flix Sep 92sexual role playing, or cross dressing, or fantasy.”

It's an extensive, not-to-be-missed interview, and the production on the magazine is top-notch. A real classic. Plus, it's oversized, and as I'm sure Madonna would agree, size matters. (She denied being a size queen in The Advocate in 1991 but...c'mon.)

A very similar magazine cover that deserves a special mention here would be New Flix (Japan, September 1991), which also contains an incredible number of Madonna photos inside.


35 Tatler 9 87 copyMadonna or bustier!


Tatler (UK, September 1987) by Herb Ritts

Herb Ritts shot many of Madonna's best portraits, and the dreamy, unique (it has never appeared as any other magazine cover) shot used in 1987 by Tatler definitely fit the uppercrust look and feel of the publication, even at a time when Madonna was doing very non-uppercrust things, like making slapstick-comedy movies and touring the world with a show that contained saucy messages about having babies and disobeying The Pope of Italy [Pope John Paul II (May 18, 1920—April 2, 2005)[ and The Pope of America [Saint Ronald Reagan (February 6, 1911—June 5, 2004)].


34 Life 12 86 Panorama Spain ?I also quite like the more yellow, less cropped version on Spain's Panorama...don't you? I'm not ranking it, but it's hot.


Life (December 1986) by Bruce Weber

Madonna-familyI love Bruce Weber more than Bruce Weber loves a high school jock model prospect with easygoing parents, but this cover isn't further up the list for me only because I kinda get stuck on the Estelle Getty (July 25, 1923—July 22, 2008) hair. It's a great pose, though, a sensational gown and, of course, a great concept: Madonna and the camera are presented as a couple. It's been her longest-lasting relationship so far, outside the one with her dad, Silvio Ciccone (b. June 6, 1931).

Inside, Weber aggressively captures Madonna cavorting with her family in photographs that are alternately endearing, energetic and, at times, a bit stagey:

Madonna-prayI feel like both subject's and photographer's giddiness over how great this shot was gonna be spoiled it.

On the last point, I just mean that Ritts was far better at capturing Madonna's elemental quality, her natural beauty, than Weber was able to do in this admittedly limited setting.

Madonna-outtakeGroovy, boyish outtake

However, Weber did far better with his effort to capture Madonna as Marilyn Monroe and as James Dean (February 8, 1931—September 30, 1955)—in both cases, he turned in winners:

Madonna-Bruce-Weber-James-Dean-Marilyn-Monroe-Life-MagazineNot surprisingly, Weber's shots of Madonna as androgyne were his best work with her.

Oh, and a parting note: I'd pay just about anything to own Madonna's outfits from this shoot, but I would not pay $40,000 to $60,000...nor would anyone else, apparently.


33 Moda Marzo 91 copyWard, weren't you a little hard on the Beaver last night?


Moda (Italy, March 1991) by Herb Ritts

I'm not wild about shared covers—only a few on this list fall under that category—but when they're done right, they're done right: The sexual chemistry between Madonna and her then-lover, the omnisexual model Tony Ward, is just oozing out of this picture, no?

1990-herb-ritts-paris-france-october-19-1990-backstage-jpg-fashion-show-moda-italy-march-1991-herb-ritts-page-13-preview-600At the time, Ward was laughed off as a boy toy. Now, he's one of the most famous male models of all time.

Shot by Herb Ritts at Gaultier's fashion show, the cover and the majestic black-and-whites included inside look nothing like casual images from an event, albeit casual images taken by a masterful photographer with his subjects' full trust and permission. Rather, the images look like stills from an erotic European '60s art film. In particular, a stark shot showing Ward gently kissing his beloved's face while she seems to pull away in feigned disgust, masking great desire, should be a movie poster, full-stop.

Tony-Ward-gay-pornA promotional poster I have for this cover is among my most treasured treasures, thanks to mega-fan Mauro Bramati, who tore it off an Italian wall.

Also much loved are my two different issues of In Touch for Men, a gay-porn mag, featuring Ward on the cover and inside. Madonna has said that she felt an affinity for Ward because of the fact that he posed nude early in his career to make ends meet, and those images later surfaced when he started dating her. Both Madonna and Ward posed nude early on, stopped, became highly successful...and then resumed posing nude. Often.


32 Rolling Stone Sep 24 1987 copyThis is the faboosh subscriber's cover, with gold logo and no non-M cover text!


Rolling Stone (September 10, 1987) by Herb Ritts

By 1987, when Madonna posed for this arresting cover (which is viewed most interestingly, IMHO, as a sort of follow-up to her True Blue album-cover pose), she was already a legend. Rolling Stone, which had smeared her in 1984, had nonetheless been following her slavishly ever since, granting her two more covers before getting to this one.

1987-madonna-rolling-stoneIn the interview inside that was conducted while Madonna was in Japan, she is compared to The Beatles, and she tries to explain the mystery behind her own appeal to the Japanese.

“I think I stand for a lot of things iin their minds. You know, a lot of kinds of stereotypes, like the whole sex-goddess image and the blonde thing. But mainly I think they feel that most of my music is really, really positive, and I think that they appreciate that, particularly the women. I think I stand for everything that they're really taught not to be, so maybe I provide them with a little bit of encouragement.”

Madonna's popularity in Japan has faded considerably over the years, but she enjoyed a massive resurgence during her Confessions on a Dance Floor (2005) era.


31 Picture Week 12 9 85 copyShoot the designer—Elvis (January 8, 1935—August 16, 1977) on her shoulder? And that icky logo. Yet...I love it. It was 79 cents in four markets, 95 cents in nine more.


Picture Week (December 9, 1985) by Bert Stern

I have to say that I think Madonna's work with Bert Stern was not as wow-inducing as one would have hoped. Though Stern did capture a lovely over-the-shoulder shot of Madonna with her hair swept up over her forehead that was right on the money (and that graced such magazine covers as Chat), this particular shot—while pretty—seems to give away Madonna's nerves at working with the last person to ever shoot (and what a shoot it was!) Marilyn Monroe, an icon she was very obviously paying homage to at the time.

It's still an utterly unique cover of a magazine that was tested from September 23, 1985 into 1986 by Time, Inc., but failed to catch on. One more Madonna cover exists (November 17, 1986—from Matthew Rolston's 1986 Rolling Stone cover session), but it's nothing like this rough-around-the-edges gem. Speaking of which, Stern said of Madonna:

“Madonna is gorgeous, the most beautiful eyes you ever saw. A little rough around the edges. She's a tough chick. She spits it out. She has her own agenda. It manifests in the pictures.”


30 Cosmo 90I think the Australian edition—with a tighter crop and more color—was pretty well, too. Image below is from the Aussie edition.


Cosmopolitan (May 1990) by Francesco Scavullo

Madonna-ScavulloMadonna rocks a Louise Brooks bob on her second Cosmo cover, which was also one of her only fold-out covers (it extends to reveal her hips and her legs to just below the knees).

Inside, in spite of being brunette on the cover, Madonna is plugging Dick Tracy in a wide-ranging interview with David Ansen, more famous as Newsweek's film reviewer and senior editor. My favorite tidbit is Madonna revealing why she hadn't been wild about her Speed-the-Plow run on Broadway in 1988—she grew weary playing a victim, and she disagreed with playwright David Mamet on who her character really was:

“It was devastating—to do that night after night. I saw her as an angel, an innocent. They wanted her to be a cunt.”

Sounds like an all-too-familiar battle in the world of Ciccone.

Scavullo's cover and variations of it have appeared on foreign editions of Cosmo, on a rare issue of Hamptons (elsewhere on this list) and on a rather out-of-character appearance on Dog & Kennel (June 1997).


29 Vogue May 89 copyOne of Vogue's first covers under Anna Wintour, who came aboard in 1988


Vogue (May, 1989) by Patrick Demarchelier

The powers-that-be (I would say powers-that-been since it was 25 years ago, but the mag still has the same editrix) at Vogue robbed us of what would've been a rare cover of Madonna with the short-lived blonde streak she had during the Pepsi era; in retouching their pretty cover pose by Patrick Demarchelier, they made her uniformly brunette. And narrowed the straps on her white bathing suit. And, oh, yeah, cut off her tits.

Madonna-DemarchelierThe original was as fetching as the final, no?

Madonna-demarchelierIt's still a brilliant cover, her first for the venerable fashion bible and, I believe, her first time working with Demarchelier, who would shoot her again with good results.

Look how simplistic the cover lines are! You can tell there was far less competition in the market back then—only 18 words on the entire cover, not counting the month/year and the magazine's title, and they fully expected it would sell. It did.

Inside, Madonna talks about money, specifically about having it:

“Well, there's a difference between being born into money and making money. I've made my money. I'm from a poor background, and basically I'm still a working-class girl in terms of my ethics.”

She also says never to be photographed in anything you wouldn't wear, then turns it out in a pair of distressed jeans, a sailor hat and a strand of pearls, among other accoutrements.


28 Excite Magazine for Men 85 86 WPB Special Selection The 72 Best Beauty Kenji Wakasugi copyIllustrious


Excite! Magazine for Men (Japan, February 1986) by ? from photographs by Kenji Wakasugi

Madonna-Kenji-WakasugiIt's a shame that Japanese photographer Kenji Wakasugi (b. ?) only got to shoot Madonna one time, because he made miracles happen with a rushed shoot in a hotel between promo gigs. His portraits of Madonna from 1985 are devastatingly glamorous, connected and sexy. Madonna was not holding back, even if she was not staring at Herb Ritts. She's wearing her HEALTHY/SWIMMER crop top, so they were probably taken just before or just after this TV performance:

Unfortunately, Wakasugi's outstanding images have never graced a magazine cover (nor has he ever, to my knowledge, licensed them for second rights). Instead, the magazine that used them, a thick, book-like publication called Excite! Magazine for Men—dedicated to female nudes—ran his images inside but resorted to an illustration based on one of the images for the cover.

Madonna-ExcitePretty resourceful shots for hotel-room snaps

I have no idea why the editors thought a drawing of a hot girl would sell better than a picture of a hot girl, and it's sad that Wakasugi's work was relegated to the interior, but I'll say this much: I have not been able to ascertain a credit for the illo, but it's sick, one of the best Madonna drawings ever—and there have been too many to count.

I've owned this magazine for years and years; I bought it from a contact in Japan for not very much money because I liked the cover (I love Madonna drawings and caricatures), and just about died when I looked inside. In recent times, the specialness of this magazine has been discovered online and it's now readily available on eBay for next to nothing. I haven't figured out why people think it's a Playboy publication, but that could be true.


27 French Glamour 6 90 copyI found my copy at the newsstand on the lowest level of Chicago's Water Tower mall...


Glamour (France, June 1990) by Herb Ritts

The highest-ranking cover on my list that features Madonna with another person is this chic mag with a beatific pose marrying designer Jean Paul Gaultier and one of the most important muses of his storied career. The two had worked on Madonna's Blond Ambition Tour and she was on the road when this hit the stands, probably having just hit the U.S. after a two-week opening in Japan. Blond Ambition was set to hit (and terminate in) France on August 5, 1990, and the anticipation would be at a fever-pitch by the time she set foot in the country, thanks in no small part to lavish coverage like this.


Inside, readers were treated to some of the original sketches for the tour's outrageous costumes, at least one of which—the conical bra—would become one of the most iconic stage costumes in history.


I must admit that the hot-pink sure looks better in a drawing than it did when revealed on stage during the latter part of Material Girl!


26 Dance Music Report Nov 27 Dec 10 82 copyMadonna's “Everybody” and Dr. Jeckyll & Mr. Hyde's “The Challenge” were sales sensations.


Dance Music Report (November 27—December 10, 1982) by Peter Cunningham

This is one of the few partial covers I'm including, but with good reasons—Madonna's the only person on the cover for one thing, and for another, DMR is the absolute first time her face ever appeared on the front cover of any publication.

If you're not sure you can appreciate how fucking long ago 1982 was musically, and how mystifying it is that Madonna's Everybody still sounds fresh today, check out how, er, dated Dr. Jeckyll & Mr. Hyde's bluntly suggestive The Challenge—also mentioned on the same cover—sounds:

This trade publication doesn't come up for sale too often. I've seen two copies in 30 years of collecting.


25 Vanity Fair April 1990 copyExpressing herself about gay people and AIDS while undressing herself for Helmut Newton


Vanity Fair (April 1990) by Helmut Newton

For the first and last time, Madonna poses here for the late, great Helmut Newton. Some fans aren't in love with the Shirley Temple (April 23, 1928—February 10, 2014) curls, but I am—and in love with everything else about this seminal magazine's cover, photo spread and Kevin Sessums (b. 1956) interview.

Madonna-Helmut-NewtonBar none

Madonna-newtonInside, Madonna flashes a bare breast for the first time since those nude photos from the '70s came out in 1985, doing so while dancing on a bar. It's all very Cabaret (1972), and has an element of genderfuck. In the feature, Madonna talks about co-opting male imagery:

“It has nothing to do with whether I am a man or a woman. I think I am a sexual threat, and I think, if anything, there is a prejudice against that. I think that it is easier for people to embrace people who don't frighten them and poke at their insides and make them think about their own sexuality. I don't do things because I may be afraid of what people might think. The thing about me is what you see is what you get. I'm not hiding naything. That may explain my longevity.”

Screen Shot 2014-07-11 at 7.59.39 PMSessums enlisted a host of A-listers to comment on the Madonna phenomenon, including Joel Schumacher (b. August 29, 1939), who remembered that Madonna had fought to be in a movie he'd written about a woman dealing with her gay brother coming down with AIDS. (Wish that'd been made.)

Madonna says of her commitment to AIDS:

“I want to do anything I can to promote AIDS education, awareness, prevention—whatever. I think because I am a celebrity, a public person, I have a responsibility to be a spokesperson. Next to Hitler, AIDS is the worst thing to happen in the twentieth century. The sad thing is that it makes people even more bigoted. It gives people a reason to vent their true feelings about homosexuality.”

Quite a deep (and long) interview for a girl promoting her fluffy role as “Breathless Mahoney” in Dick Tracy, a summer movie based on a comic strip.

You can read more about what Sessums recollects regarding his encounters with Madonna in his new memoir I Left It on the Mountain (St. Martin's, February 24, 2015, $25,99). I haven't read it yet, but his last book, Mississippi Sissy (Picador, 2008, $17), was top-notch.


24 Spin 5 85 copy“My favorite button is my belly button. I have the most perfect belly button: an inny, and there's no lint in it.”


Spin (May 1985) by Herb Ritts

Those aren't freckles, it's black sand—and Spin's first issue was lucky to land one of the most beautiful closeups from a Hawaiian shoot by Ritts that found its way into Madonna's Virgin Tour program. Just a few months later, Spin's publisher Bob Guccione Jr.'s (b. September 19, 1955) father would be landing nude images of Madonna for his own publication, Penthouse.

Madonna-Spin-1985-Curtis-KnappMadonna's Spin cover was a big seller, thanks in part to a novel (or should I say navel?) interview with its cover subject, in which she confesses a variety of things, like:

“I like to look the way Ronnie Spector sounded: sexy, hungry, totally trashy. I admire her tonal quality.”


“When I was growing up, I was religious, in a passionate, adolescent way. Jesus Christ was like a movie star, my favorite idol of all.”

...but most famously...

“Crucifixes are sexy because there's a naked man on them.”

For the magazine's 20th anniversary, the same cover was reissued. The print aspect of the publication ceased in 2012, but it's still available online.


23 Max Sep 87 copyThe cover line works as both, “Madonna, I love you!” or Madonna: “I love you.”


Max (Italy, September 1987) by Herb Ritts

Madonna-Max-Italy-September-1987I'm not a huge fan of Madonna's career in 1987—I thought the movie Who's That Girl was pretty bad (and badly in need of a question mark) and found that some of her imagery from that year, unlike the witchy trash look from '85 and the streamlined gamine from '86, came off as oddly punk-matronly—her hair was white-blonde, but looked styled under a dryer at the hairdresser's. Sometimes.

But on Max, Madonna couldn't look better, presenting her face in a Herb Ritts masterpiece from sessions used in merchandising and to plug her excellent Who's That Girl Tour, which was the first tour during which she displayed some of her blond ambition when it came to giving the people a layered live show, even though it, too, could've used a question mark.

Inside, Madonna's face appears on 15 pages, including dazzling performance shots, a Ritts shot of Madonna with very short brunette hair and a few images by Alberto Tolot of Madonna with her WTG movie monkey purse and black plastic dress.

The magazine is enormous, weighing in at six or more pounds. Therefore, any copies you find today are likely to have severely distressed spines...not good news for collectors who demand that everything be mint.


22 Face 2 85 copyWill you marry me?


The Face (UK, February 1985) by Steven Meisel

In her home country, Madonna has had Interview, Rolling Stone and Vanity Fair to document nearly her every move. Among the UK magazines that have relentlessly covered her is The Face, and her first appearance on it was this warmly-lit Steven Meisel image from her Like a Virgin packaging shoot.

Madonna-MeiselWith styling by Maripol, this bride of Satan look was quintessentially Madonna.

In the interview, illustrated with an eye-popping shot of a presumably nude Madonna covering herself with blue silk sheets, our girl professes to be a fan of gay group Bronski Beat and actresses Marilyn Monroe, Carole Lombard (October 6, 1908—January 16, 1942), Jessica Lange (b. April 20, 1949) and Susan Sarandon (b. October 4, 1946). She also explains her reliance on her sexuality in her work:

“From when I was very young, I just knew that being a girl and being charming in a feminine sort of way could get me a lot of things, and I milked it for everything I could.”

The Face had actually been one of the first UK publications to cover Madonna in '83, with a two-page spread featuring a majestic B&W portrait of the then-new disco dolly by Kate Simon (b. ?).


21 New York PostMadonna has been famous since the days when Reagan was on the warpath.


New York Post (July 9, 1985) by David McGough

When Madonna's nude-photo scandal hit in 1985, the New York Post tabloid was johnny-on-the-spot with a cover capitalizing on the issue. Interestingly, the cover itself did not condemn the popstar, instead allowing her to have her say, and say it she did: “'I'M NOT ASHAMED'.”

Madonna-wedding gifstHaring & Warhol arrive at Madonna's wedding with art based on the two versions of this cover published by The New York Post on July 9.

So electrifying was the simple cover—with a pretty shot of Madonna partying at her Palladium Virgin Tour party as captured by David McGough—that Madonna's good friend Keith Haring fashioned it into an important piece of pop art.

Madonna-New-York-PostThere was one other variation of this cover that appeared the same day with a different photo [a cropped image by Lee Friedlander (b. July 14, 1934), whose nudes of Madonna were about to heat up Playboy].

This variation—which was a later edition from that same day—had the headline: “MADONNA ON NUDE PIX: SO WHAT!”. 

Madonna-HaringImage via Pud Whacker

When Haring and Warhol collaborated on their art pieces, one of the pieces was simply a painted-over silkscreen of the early edition of the Post, while another piece was made using the very latest (final) edition of the Post from that day. Inexplicably, the Post had removed any image of Madonna from the final edition, so the artists used a Haring Polaroid of Madonna and Sean from Live Aid (July 13, 1985) to cover over an image of a random woman trying to stay cool in the NYC heat.

Check out Pud Whacker's Madonna Scrapbook for an endlessly good, Madonna-saturated time. Also, I do not own the Friedlander or non-Madonna editions of this newspaper and would like to, if you have copies for sale.


20 Interview 12 85 copyThe signature is a facsimile, but the gaze is pure Madonna.


Interview (December 1985) by Richard Bernstein from images by Herb Ritts

Madonna's first appearance on Andy Warhol's Interview—and her only appearance on the magazine during his lifetime—was this exquisite creation; the cover image is a work in pencil, pastels and airbrush by Interview's longtime artist-in-residence Richard Bernstein (who died of AIDS in 2002) inspired by images taken for the magazine's interior by Herb Ritts.

Madonna-Interview-Richard-BernsteinThe full work of Madonna by Bernstein, signed and dated 15 years after its inception.

Madonna-InterviewRemember when magazines were important? In case you've forgotten, get your hands on one of these. Madonna's appearance on Interview is one of the largest magazines on which she's ever appeared and weighs a ton—all those ads!

It's a coffee-table book, and it's filled with quality work, including stunning black-and-white images of Madonna and her then-husband Sean Penn by Ritts. Bernstein's cover remains one of the most unusual and loveliest in Madonna's career.


19 The Face June 1990 copyNow sneer this!


The Face (UK, June 1990) by Jean-Baptiste Mondino

Madonna-FaceAt the same time Harper's Bazaar was dropping in the States with an edgy Mondino cover, a nearly equally fabulous Mondino cover was making a splash in the UK—and what a great cover it is!

Madonna had been known as a bit of a brat in her early NYC days, and things were not getting better, but worse—her divatastic behavior throughout 1990 was being filmed for 1991's Truth or Dare and it would reach its zenith with the period between 1992 and 1994, when Madonna was being beaten up in the press and having a sort of personal meltdown.

But back in 1990, before the brattiness went nuclear, a sneer like this from Madonna was cute to her fans. Here was the bitch goddess, commanding you to suffer—and enjoy it. As a bonus, she appears to be giving us a little vogueing action.

Madonna-The-FaceThe unretouched image shows very little work, though even then Madonna's hands were micro-managed.

Inside, the issue chronicles the making of Dick Tracy and refers to Madonna as “Mini Marilyn” and a “Baby Dietrich.”


18 Penthouse 9 85 copyThe addition of a gleam on the cross is inspired.


Penthouse (September 1985) by Ken Regan

If her Desperately Seeking Susan look weren't so overwhelmingly powerful, I'd have to place Penthouse's 1985 cover above Playboy's 1985 cover on this list—and as it is, it's still pretty close! Penthouse, like Playboy, had arty black-and-white images of Madonna on the inside (by Bill Stone, whose work does not command the bucks Playboy's by Lee Friedlander later would) but desired a more current, colorful image for its cover. In this case, they went with a Ken Regan shot that had been taken during his shoot for People earlier in the year.

MadonnaStone fox

Madonna's look in the Regan shot is pop perfection, and her vintage tank became so familiar to fans it was auctioned off in 2014 for the rather healthy sum of 15 grand. Slides of Stone's work that were used in the production of the layout, which remained with Penthouse's Bob Guccione, were auctioned off (some of them realized no bids) this year as well.

It may seem perverse to include both Penthouse and Playboy in the Top 20 greatest Madonna magazine covers considering they were done without her permission and upset her quite a bit at the time, but as with many other aspects of stardom, the stars themselves can't choose what captures the public's and/or their fans' imaginations, and in my mind, there is no denying how big an impact both of these covers had in building Madonna's image or legend, if you will.


17 Quiet Storm 12 84 copyI'm crazy about the title font, too.


The Quiet Storm (Thailand, December 1984) by Deborah Feingold

When you're talking about rare Madonna magazines, you have to talk about this exceptionally scarce, newsprint-stock magazine sporting an otherwise unseen portrait of Madonna by Deborah Feingold. One of Madonna's earliest Asian covers, it's also highly unusual for its lack of eye contact, which makes it look more like an art piece than a mass-marketed entertainment mag.

Considering this low-circ, fragile giveaway was produced before Madonna became a Thai-household name, it's a wonder any copies exist at all. It's not clear how many actually do, but the publication only rarely changes hands—and for over $1,000—among collectors.

Deborah-FeingoldIn September, Feingold will have an exhibit of her '80s Madonna images...too bad they can't spell the woman's name!

Feingold took quite a number of excellent, early images of Madonna, some of which became memorable covers, especially later on once Madonna portraiture became hard to come by and/or required PR approval—early shots had no such requirement.


16 BAZAAR 6 90 copyThinking of going for the jugular? Like to see you try...


Harper's Bazaar (June 1990) by Jean-Baptiste Mondino

Rescue-me-uk-promo-display-counter-stand-2435-pModeling Gaultier duds, some of which would turn up on her Blond Ambition Tour of the same year, Madonna looks sleek and lethal on this Bazaar cover...just look at those scary metal teeth around her tender throat!

With an uncharacteristic wet-look hairdo, Madonna glares at the camera with supreme self-satisfaction. She was ostensibly plugging her movie Dick Tracy as well as her tour, but she looks every bit the 1990 Madonna character and about 0% like 1930s “Breathless Mahoney.”

One of my favorite images from inside—of Madonna in a supertight silver lycra top (pictured)—was later used as a UK in-store counterstand promoting the 1991 release of her single “Rescue Me.” It's...bodacious.


15 Playboy 9 85 copy


Playboy (September 1985) by Herb Ritts

Playboy's last stapled issue was, as its cover promised, definitely a keeper, but not because there are so many fans of staples out there—the main attraction is that sultry Herb Ritts image of Madonna in Madonna-PLAYBOYfull Desperately Seeking Susan regalia.

At the height of Madonna's initial burst of fame in 1985, with two hit albums, a string of hit singles and a hit movie behind her, news broke that nude images she'd posed for years before were set to appear in the September issue of Playboy magazine hitting the street on July 10, 1985. (And Penthouse, in a copycat move, snapped up its own older nudes of the Material Girl and rushed out an issue at the same time.)

Like Marilyn before her, Madonna had posed nude to make ends meet before her career started. Lucky for Madonna, she posed mostly for highly artistic (if 100% revealing) images, so that any impact more pornographic images may have caused was blunted. The Playboy nudes, shot by art photographer Lee Friedlander in 1978, revealed Madonna's lithe dancer's body, lovely breasts and tendency toward the hirsute—women were not as likely to remove all their pubic hair back then, but Madonna's hairy armpits were definitely not the norm.

Madonna was said to have been rattled by the revelation, fearing even that she was about to lose her career. Instead of freaking out, she sucked it up and appeared, as scheduled, on July 13, 1985, at Live Aid. Bette Midler (b. December 1, 1945) introduced her with a crack about letting her bra straps down, but Madonna—overdressed for the steamy-hot day—cursed on live TV, vowing, “Naw, I ain't taking shit off today. You might hold it against me 10 years from now.”

It wasn't because she was shy or embarrassed—it was because she was pissed off and was taking back control.

Playboy got away with using the Ritts image free because it was an Orion promotional shot for her movie. It's an iconic shot, but imagine if Playboy had been a little more daring and used a closeup of one of the Friedlander black-and-whites?

Incidentally, by the numbers: Friedlander paid Madonna $25 for the session, he was in turn paid $100,000 for scant shots used by Playboy and an original, silver gelatin print from the same time period sold at auction in 2009 for $37,500. Love don't make the world go 'round, money does.

And tits, don't forget tits.


14 FM April 1985 copyGotta believe that in 2014 they'd have PhotoShopped the strawberry to be completely red...


FM (Japan, February 11—24, 1985) by Hiro Itoh

When Madonna hit Japan on a Like a Virgin promo tour in early 1985, many wonderful things came of it, including TV appearances in which the glammed-to-the-hilt street urchin awkwardly listened to hosts raving about her in Japanese before receiving translations, gamely lip-synched her hits (you can practically hear the wheels turning in her head telling her, “No one in America will ever see this!”), attended press conferences and—best of all!—posed in impromptu shoots with Japanese that for many years were almost unknown to U.S. fans.

It would be a cold day in hell before Madonna would again casually pose for photographers in sessions like these, all the more reason to cherish the images that emerged from her time with the Japanese shooters.

Though there are several examples of Japanese magazines from 1985 with rare images of Madonna inside, the cream of the crop is the one that wisely decided Madonna was cover-worthy.

Madonna-hotel-1985In giving Madonna the star treatment, FM went on to be one of the only Japanese magazines that ever ran a completely exclusive image of Madonna (even her best, most desirable covers were usually just recycled images from U.S. publications) on its cover...and the image of Madonna playfully preparing to eat a strawberry, while it's just a snapshot in her room between TV gigs, is an adorable portrait that made for a memorable cover indeed.

Inside, the magazine generously offered another half dozen only-seen-here images of Madonna in her hotel room, plus a couple of live-performance shots. 

It's got a strawberry on the cover, but it's a peach.

(Note: The magazine is often misidentified as FM Fan or as FM Weekly. However, the interior feature makes clear that the FM stands for Face Magazine. Also, I believe that while there is a 4 on the cover, this magazine was not April 1985, but was—as is indicated on the upper right of the cover—a two-week publication from February of that year.)


13 British Vogue 2 89 copyLike a girlier Joan of Arc


British Vogue (UK, February 1989) by Herb Ritts

I still love looking at this unique, fashiony cover, which came out in advance of the release of her Like a Prayer album. I remember when I first found it—I was scouring magazine stores in Chicago, Madonna-British-Vogueas I did often in those days before the Internet told us when to expect new issues, and spotted this in a tony store on Michigan Avenue. It was like using a metal detector to find a gold dubloon on a public beach.

Madonna had gone brunette in the controversial video for the debut single, but seeing her hair straightened and her face with this hard-to-read Queen Christina (1933) expression was a new experience—Madonna was staring into the future and embracing a kind of maturity. Even her haute couture clothing was a far cry from her Boy Toy days.

As mayjuh as the cover was, the piece inside was tiny, albeit decorated with two more gorgeous images of Madonna in a Lacroix Luxe chiffon slip (and her own black tights, shoes and crucifix). In the story, which was written while Madonna was dancing to Prince at the Ritts photo shoot, she explicitly states she is trying to represent the real her. She also speaks about her intentions with Like a Prayer:

Lika a Prayer is about the influence of Catholicism on my life, and the passion it provokes in me. In other songs I've been dealing with more specific issues that mean a lot to me. They're about an assimilation of experiences I had in my life and in relationships. They're about my mother, my father and bonds with my family, about the pain of dying, of growing up and letting go. I've been exploring different kinds of music and discovering things inside me that I suppose have always been there, but I've never had the confidence and experience to show them until now.”

Turning 30 will do that to a girl.


12 Long Islands NightlifeA mixed bag of fellow celebs in the issue: John Travolta, Donna Mills, Billy Hufsey, Maureen McGovern & Frankie Valli!


Long Island's Nightlife (September 1984) by Gary Heery

So, lookit...I want this magazine. If you have one, let me buy it, okay?

One of Madonna's earliest magazine covers (the number of times she appeared on a magazine cover prior to 1985 is infinitesimally small compared to the numer of times she appeared on a magazine cover in 1985, let alone after 1985!), Long Island's Nightlife is a great example of a cover that has it all: A beautiful image of Madonna, a rare image of Madonna (I don't believe any other magazine ever used this shot), an early image of Madonna (this is from her second try at a first album cover shoot) and extreme rarity—the print run of the magazine was negligible, considering it was a small nightlife magazine catering to only NYC's Long Islanders.

This magazine's cover and feature were Xeroxed by Warner Bros. and included in press materials for her Virgin Tour in 1985, but otherwise is actually scarcer than even Madonna's very first cover appearance, on Island (October 1983). Only one copy has been publicly sold in the past decade—and it went for $2,000 on eBay in 2008.

Why? Because: She's Madonna.

I don't own the magazine (and want to), but I do own the chain around her neck, so that's my consolation prize.


11 Vogue Italia 2 91 Brasil Vogue 1991The same shot from Vogue Italia (February 1991), cropped and tinted, decorates Vogue Brasil (Brazil, June 1991)—a hard issue to find.


Vogue Italia (Italy, February 1991) by Steven Meisel

Madonna-Sex-promoThat famous image (seen at left) of Madonna in what collectors/fans called her “jeweled bodysuit” from the Sex era (October 1992ish) has nothing on the variation that appeared on the cover of Vogue Italia almost two years earlier. Meisel really knew what he was doing when he put Madonna into that alternately sheer and gaudy barely-there outfit, and Madonna really knew what she was doing in it. Granted, the image has been retouched with a heavy hand, but unretouched variations show Madonna looking every bit as sexy if not quite as perfect.

Madonna-Vogue-ItaliaInside are glorious, full-page images of Madonna “as” Marilyn Monroe, which wasn't the first time we'd seen that but was definitely the most interesting and least literal stab at the concept.

One of the all-time best images ever taken of Madonna first popped up here—Madonna in Marilyn drag, yet with a far more aggressive demeanor, absent-mindedly fondling one of her bare breasts while clenching a cigarette between her lips. She's never looked hotter, more modern, more transgender. It's got to be one of Meisel's crowning glories from his many shoots with her.


10 Hamptons 7 4 85 copySuch a tease!


Hamptons (July 4, 1985) by Francesco Scavullo

When it comes to Madonna magazines, I own just about all of the ones I want to own. Not so for this extremely rare publication, which is newsprint inside but has a glorious glossy cover. (I actually own the cover, having found it in a collection of clippings on eBay.)

The image is from Madonna's 1985 shoot with Francesco Scavullo, the late, great queen of the Cosmo cover. He shot her for Cosmo, and also for a magazine that appears a little higher up on this list: Time '85.

Madonna looks witchy and gorgeous in this rarely-seen image, even with a fold through her nose.


9 i-D March April 84 copyMaterial Girl George


I-D (UK, March/April 1984) by Mark Lebon

I almost died when I received this magazine in the mail six or seven years after it had first hit the Id4newsstand in the UK; I'd ordered it blind from an ad in Goldmine, never having heard that Madonna was on the cover and assuming the description was off. It wasn't. Madonna was shot by Mark Lebon looking very Boy George and sporting neon-pink lipstick. Her styling for this shoot was significantly dissimilar from any look she wore in public at the time, and the image remained utterly singular until Lebon's outtakes leaked (see example at left) many years later.

Madonna illustrates the theme of the issue, but there's no article inside. Still, it's a unique and hard-to-find piece of Madonnabilia...and it's 30 years old already.


8 Rolling Stone 11 27 84 Paris Match 12 18 87Printing and color separation are everything—see how different the same (almost the same) image looks under different direction?


Rolling Stone (November 22, 1984) by Steven Meisel

Madonna's gaze is one of the secrets of her success as a photographic subject; she controls the mood of most of her photographs with the greatest of ease, with the flick of an eyelash, or, as in this case, with her hardened, unblinking stare.

Little did she realize that this prime image by Steven Meisel would be used to enhance journalist Christopher Connelly's (b. ?) exceedingly cynical profile—her first in the rock rag of record. It became a piece she would never fully live down, a story that broadcasted its intentions with that cover line: “MADONNA GOES ALL THE WAY,” in all caps.

The article basically laundry-lists every person Madonna met and worked with, more than implying that she coldly used them to get what she wanted, and then discarded him. When commenting on her past association with Stephen Bray (b. December 23, 1956), Madonna says:

“Looking back, I think that I probably did make him feel kind of bad, but I was really insensitive in those days. I was totally self-absorbed.”

To which Connelly adds:

“It wouldn't be the last time.”

In spite of the magazine's sexist-feeling treatment of her, this also wouldn't be Madonna's last appearance on the cover—she would return with almost every album project over the years, proving that if she didn't love that first profile, she still knew Rolling Stone was establishment—something she wanted to be part of, something she wanted to affect.


7 Time 5 27 85 copyShe bangs


Time (May 27, 1985) by Francesco Scavullo

Madonna's stardom was confirmed by a dedicated Time Magazine cover, featuring a striking portrait by fashion photographer Francesco Scavullo. The cover promised to explain—to the non-teenaged masses—why exactly Madonna was the girl of the moment. Inside, the piece was all in first person, with Madonna all but writing her autobiography (which elsewhere she has promised not to do until “I'm a really old lady”).

While discussing her style, Madonna gives a very early shout-out to Gaultier, who would become essential to her look in the future:

“I like to combine things but in a humorous way, like a uniform skirt and fishnets. Sometimes I like really expensive things. I like Vivienne & Westwood, Commes des Garçons and Jean Paul Gaultier. But I get a lot of stuff in thrift shops too. I really love dresses like Marilyn Monroe wore, those ’50s dresses that were really tailored to fit a voluptuous body. A lot of stuff made now is for an androgynous figure, and it doesn’t look good on me. I have always sort of elaborated with my dance clothes. I used to live in my dance clothes, my tights and leotards, but I always personalized them. I’d rip them all up and make sure the runs got really big and had a pattern to them. I started wearing bows in my hair because one day when my hair was long, I couldn’t find anything to tie it back. So I took an old pair of tights and wound them around my head, and I liked the way that looked.”

She was also still answering questions about her name back in '85:

“My mother is the only other person I have ever heard of named Madonna. I never had trouble with the name. Not in school or anything, of course. I went to Catholic schools. And then when I got involved in the music industry, everybody thought I took it as a stage name. So I let them think that...It’s pretty glamorous.”

It's a shame Madonna only worked with Scavullo a few times—he had a real flair for getting drama out of every shot.


6 ADVOCATE copy copyNo teeth!


The Advocate (May 7, 1991) by Steven Meisel

SPOILER ALERT: My entire Top 5 is made up of oh-so-pretty Madonna covers. But this unforgettable cover at #6 deserves a spotlight for its perfect capturing of Madonna's blatant sexuality, her sense of humor, her theatricality and her connection with gay men. (Just a few years later, the magazine would ludicrously choose her as its “Sissy of the Year” simply for mentioning that she is not, in fact, a lesbian.)

This Meisel shot is Truth-or-Dare fabulous, daringly shows off Madonna's nipple in her see-through bra and delivers an interview with Don Shewey (b. ?) which, if not exactly as X-rated as advertised, is phenomenally interesting and was instantly controversial. This is the one where she offhandedly outs her brother Christopher Ciccone (b. November 22, 1960) in the context of laying out her entire history with the gay community.

She also presents how vogueing came to her, and how she decided to co-opt it:

“I went to the Sound Factory with my girlfriend Debi M. [Mazar] because I wanted to go dancing. At the time I was trying to visualize things for my show, and I was hanging around a lot of clubs—watching different styles, looking for dancers. I don't like the people who go to class all the time; they're really boring dancers. I was just looking for some street dancers, you know, and when I saw Jose and Luis dancing, I was completely blown away by them. I was afraid to approach them.”

Asked if she'd cut anything out of Truth or Dare, Madonna replies:

“There's a lot of stuff with Warren that I cut out—there were phone conversations I thought were really moving and touching and revealing, but Warren didn't know we were recording. It wasn't fair, plus it's a federal offense.”

There's so much more. (It was printed in two installments, in two successive issues of the gay newsmagazine.) I think to this day it's the ultimate Madonna interview. Where else would we ever have found out that Warren Beatty regretted not having sex with men before AIDS came along, that Madonna isn't interested in dildos and that Sandra Bernhard's (b. June 6, 1955) dick is:

“Huge. It's the biggest dick I've ever seen.”


5 Vanity Fair 12 . 86jpg copyOne can easily picture Madonna's 1990 Marie Antoinette turn already sprouting in her fertile imagination. 


Vanity Fair (December 1986) by Herb Ritts

In 1986, Madonna consciously discarded most of the iconography that had so recently helped transform her from just another starving mouth hoping to feed itself on the mean streets of NYC into a strong contender for the most important female pop-musical figure since Patti Smith (b. December 30, 1946), if not—gasp!—even back to Connie Francis (b. December 12, 1938). The transformation Madonna-outtakehad been a big hit, and she ended the year with a third album even bigger than her second, which had been even bigger than her first.


For Vanity Fair, Herb Ritts—the photographer who captured Madonna's beauty more consistently than any of her collaborators—presented Madonna, via a regal pose highlighted by her white-blonde (or was it almost bordering on lavender?) 'do and maroon lips and nails. This cover is unquestionably one of the most striking images ever taken of Madonna, making her look like someone whose head the French would've been tempted to cut off a couple of hundred years earlier.

Inside, in a piece prophetically entitled “Classic Madonna”, Michael Gross (b. ?) interviews the ever-expanding superstar and turns in several amazingly insightful quotes from other sources we're forever grateful he contacted for their input.


For example, designer Travilla (March 22, 1920—November 2, 1990), who created looks for Marilyn Monroe in 11 (!) of her films, points out of Madonna that by trying on different looks and aping different stars' poses:

“She's searching for herself.”

This simple observation goes so much further than all the accusations of shallow copying, especially when paired with the following quote from Madonna's Goose and Tomtom costumer, Kevin Dornan (b. ?):

“I think she does a lot of homework. She's consciously trying to evoke her idols, but she's enough of a star to fit each style and make it her own.”

Photographer (of Monroe) Arnold Newman's (March 3, 1918—June 6, 2006) comparison of Madonna to Streisand is sort of brushed off by Gross, but damned if he wasn't drop-dead right.

The piece also has plenty of great Madonna quotes, but let's let this one be the best:

“I don't eat any flesh. Vegetarians are paler.”


4 Tatler March 86 copyThe turban sombrero


Tatler (UK, March 1986) by Herb Ritts

Considering the fact that Tatler is a major publication in the UK, it's surprising to me that finding this unique Ritts cover of Madonna is still a bit of a challenge. Prior to the Internet and eBay, it was Madonna-Tatler-adone notch below Island (October 1983) in terms of being a Madonna-mag Ark of the Covenant.


The image is almost completely unique—how many variations on this pose taken the same day have you seen?—and presents Madonna as an exquisitely beautiful, Olympus-ready goddess, complete with amazing '80s silver jewelry, her signature cross and those adorable mink eyebrows we all (except for Madonna herself) miss.

Inside? No Madonna. Go figure. She's just there to illustrate the cover line “White Heat”, which was also, coincidentally, about to be an album track on her record True Blue.


3 Interview 6 89  copyThis promo poster of the cover has just Madonna's name, with a red exclamation point.


Interview (June 1990) by Herb Ritts

Shortly after Michael Jackson's masturbatory crotch grab became a signature move for him, Madonna mirrored it in her “Express Yourself” (1989) video—it wasn't a matter of Madonna doing the Madonna-Interviewsame thing; a woman couldn't do the same thing a man did and have it mean the same thing. It was a witty, ballsy commentary on gender equality. And on the size of her dick compared to yours.

Madonna's crotch grab was immortalized by Herb Ritts on this, their greatest cover together, a cover unlike any other they ever shot (though alternate images from this shoot would go on to decorate many other magazines all over the world).

The images were so intensely successful, capturing Madonna in her Blond Ambition “Holiday” top, with a short black wig and even highlighting her tooth-gap, that they were also used in the packaging for her first greatest hits package, The Immaculate Collection. It's Madonna's best-selling record.


2 Vanity-Fair-CosmoThe Japanese Cosmo (July 1991) is very rare. Always liked how sunkissed Madonna looks on it.

#2 TIE

Vanity Fair (April 1991) & Cosmopolitan (Japan, July 1991) both by Steven Meisel

Madonna-Steven-Meisel-Vanity-Fair-1991Unlike some of Madonna's greatest magazine covers, one of these isn't that hard to find and won't set you back too many dollars when you find it. Still, I think Madonna's Meisel cover (the two are seen together at the shoot at left), released at a time when she was arguably at the very peak of her powers, is—as Madonna would breathlessly post on Instagram today—#iconic.

That cover was so hot she wore the same duds to the Oscars. With Michael Jackson. #iconic


Madonna had winked at Marilyn Monroe many times earlier in her career, and seemed to finally realize her ultimate Marilyn tribute under Meisel's direction. Though on the cover she looks to me more like a resolute Lana Turner, the Monroe Doctrine is crystal clear in the beautiful interior spread, which leapfrogs from early to late (very late—try Bert Stern) Marilyn references.

Madonna:Marilyn Madonna-Marilyn-2Inhabiting the same general poses, but not Xeroxing

In the interview, Madonna speaks at length about what we can all agree is one of her greatest projects of any kind—and it's a movie!—Truth or Dare. She confirms she was going for shock value, but, as always, the kind that serves the purpose of reminding people of how provincial they are to be shocked by what shocks them. Of the film's gay kiss, she says it's:

“ favorite scene in the movie. I love that people are going to watch that and go home and talk about it all night long. I live for things like that.”

And I live for Madonna re-inventing Marilyn Monroe in 1991.


1 IslandGot my copy by placing a $50 (!) bounty on it in an ad in NYC's Loot 20 years ago...


Island (October 1983) by Curtis Knapp

Other people who've made lists of Madonna's best magazine covers have chosen Island; it's sort of like how Citizen Kane (1941) winds up on most best-movies lists. But as with Citizen Kane, it would be shameful not to acknowledge just how amazing Island really is, especially for a first cover, so pretending it's not her greatest magazine cover just to avoid looking conventional wouldn't be fair.

Madonna-KnappPrints of Knapp's outtakes are marketed by Madonna's current manager.

Most celebrities' first full magazine covers consist of a crappy PR photo, but Madonna's very first time boasts a brilliant image by Curtis Knapp that captures her beauty, creates the edgy look the then-new, Downtown magazine was going for and manages to prefigure Madonna's obsession with quoting the images of other great stars before her—in this case. Greta Garbo by Edward Steichen (March 27, 1879—March 25, 1973).

Madonna-GarboThe only public figure with less in common with Madonna than Garbo might be J.D. Salinger (January 1, 1919—January 27, 2010)!

Steven-Meisel-Madonna-1983The magazine also contains a juicy interview, in which Madonna jokes that she's in love with her then manager Freddy DeMann (b. ?), talks about phallic symbols and Catholicism and describes her stage style as a:

“...pseudo-Puerto Rican punk rock freak out. A motorcycle baby. It's a combination of my two oldest fantasies. One was to be Nancy Sinatra; the other was to be a nun.”

The image used inside was an early Steven Meisel image of Madonna—he holds the record for the photographer who has worked with Madonna, sporadically, over the longest period of time: 30 years, so far.

Island had an extremely low circulation in spite of warranting a release party and sporting such irresistible cover lines as “FASHION” and “POLITENESS”. It always sells for over $1,500 and sometimes over $2,500 on eBay...where it appears only rarely.

Madonna island roxy inviteDon't you wish you'd been there?

Madonna could not have asked for a more sterling first magazine cover, and any serious Madonna collector has to have this—just be advised when cutting a deal to sell your copy to a Madonna collector that unlike the others, they'll do anything, they're not the same, they have no shame.


That's it! The full list. I hope you enjoyed it, even if you obviously will have thoughts on some of my choices.

Once again, please help me out by donating to my first Kickstarter campaign so I can get a 20th Anniversary edition of my book Encyclopedia Madonnica into your hands! Just click here.