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Sep 19 2020
Like A Casting Agent: Who Could Be Who In The Madonna Biopic Comments (0)

Chloe-grace-moretz-madonna-movie-boycultureThere's one thing you miss ... and ... that's ... Moretz? (Images via IG & Herb Ritts)

Madonna's biopic may have seemed like a lark at first, but then again, revealing she was earnestly working on a screenplay with the seriously talented and successful Diablo Cody was probably a tip-off that movie-wise, Breathless was back in business.

Now that she has forced Universal's hand — the studio announced that the as-yet-untitled biopic will be produced by Amy Pascal and directed by non-charlatan Madonna herself — it's time to realize that this movie, its fortunes perhaps buoyed by the hits that were Bohemian Rhapsody and Rocketman, could be not only an eventual reality, but on the proverbial fast track.

Presuming a suitable screenplay is completed within, say, another couple of months, and presuming that filming is not hopelessly hamstrung by the coronavirus, the movie could feasibly drop as early as 2022. 

In honor of this coming triumph or disaster (I am rooting for a triumph), I have taken a little time to list just a few of the people who may be depicted in the movie, and to cast them. You're welcome, Madonna!!!

It is impossible to know who will make the cut, because in order to squish the legend of Madonna into two hours, heads must roll. One could come up with dozens of ways to frame her life and career — imagine how different a biopic entitled Live to Tell would be from one entitled, say, Burning Up. Therefore, I am choosing almost 80 people who could appear in some capacity.

I wish Madonna and her team all the best, both for their own success and for selfish reasons — because what inveterate Madonna fan would not fucking love to have her make a brilliant movie about her life that reveals crazy secrets, cements her status as one of the most important and impactful artists in history and, I dunno, wins an Oscar or four?

My dream cast ...

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The Star

Elena-kampouris-madonna-boycultureKampouris/Madonna (Images via IMDb/by Richard Corman)

Madonna — Elena Kampouris, Chloë Grace Moretz, Grace Van Patten, Sky Ferreira

Guys, guys ... nobody is going to be a perfect match to play Madonna. The pretty girls are often too bland, the punky girls often lack glamour, so we're gonna to have to find someone who can suggest her in such a way that the casting is not a distraction. (In other words, whoever she is, she should not be too obvious, either. No Gaga.)

Sky-ferreira-madonna-boycutlureFerreira (Image via Instagram)

These women, to me, have beauty, brains, star quality and (though I have no clue if Ferreira can act) could probably credibly pull off Madonna's youthful feral charm.

Grace-van-patten-selfie-boycultureVan Patten (Image via selfie)

Still, don't count out dark-horse contenders like Taylor Momsen, who isn't a good fit, IMO, but who Madonna has hired in the past (to promote her Material Girl line), or Paris Jackson (who would be slimed as stunt casting and probably never really be given a chance).

Also, we can't know if Madonna will cast multiple women to account for the aging process (or to make this Ciccone Joint a Palindromes affair) — older Madonnas are tantalizing to consider. Mid-career ... Amanda Seyfried? Confessions ... Jessica Chastain? The mind boggles.

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The Family

Mara-wilson-boyculureWilson & Ciccone Sr. (Images via video still & family photo)

Madonna Ciccone Sr. — Mara Wilson

I like the idea of former child star Mara Wilson as Madonna's mother, the idea of someone who dealt with fame young embodying a woman who had zero to do with it, and yet who accidentally became responsible for the most famous woman alive. Also, hard as it is to believe, Wilson, just 33, is already on the cusp of being too old to play Madonna's mom — Madonna Sr. aka Big Madonna died at 30. Melanie Lynskey also favors Big Madonna, though she's already 13 years older than her at the time of her death.

Michael-shannon-boycultureCiccone & Shannon (Images via family photos & Paramount)

Silvio Ciccone — Michael Shannon

I had a tough time casting Madonna's dad, the man who loves her, is proud of her, is embarrassed by her, tolerates her, supports her, castigates her and gave her something to rebel against. No Italian men in their 40s/50s leapt out at me. I settled on Shannon because I can see him bringing the troubled and taciturn the best. Plus, she is likely to cast someone A-list to play a man who is so important to her.


SourceCiccone & Coolidge (GIFs via GIPHY)

Joan Ciccone — Jennifer Coolidge

It depends on the ages at which Madonna's stepmother is shown, but I think of Jennifer Coolidge as ageless, and I say she can pull off 35-80 if she has to.

Boyculture- joey-pollariCiccone & Pollari (Images via personal photo & video still)

Christopher Ciccone — Joey Pollari

Christopher was a huge part of Madonna's early and middle life, then betrayed her savagely with a petty tell-all book. He was around for her embrace of gay men, her early club gigs and even directed her Girlie Show Tour. Though Christopher could never be said to have had the impact on Madonna's career that he believes he has, he is nonetheless a must-have for the movie. Plus, this could be a good opportunity for Madonna to get some revenge. After all, however he is portrayed here, he won't be able to follow up with a Diablo Cody-Amy Pascal movie about things from his POV. I like Joey Pollari for this. He is a good age, resembles young, hot Christopher, and as a bonus is actually gay. — Love, Matthew.

Julia-garner-paula-ciccone-boycultureGarner & Ciccone (Images via Netflix & Blitz)

Paula Ciccone — Julia Garner

Honestly, I'm shocked Paula rates so much play in the screenplay, according to Madonna and Diablo's own comments, and I am super intrigued. Perhaps she will illustrate how someone with (as Madonna says) more talent still doesn't have the X factor, and has to live with being so close, and so far, from fame and fortune? I think she has as much chance to be cast as Madonna, but for whatever reason, because Madonna and Diablo suggested Paula will play an important part of Madonna's story, I gravitated to Julia Garner as Paula.

Liana liberato boycultureLiberato & Ciccone (Images via video still & family photo)

Melanie Ciccone — Liana Liberato

We rarely see Melanie Ciccone, Madonna's younger (by four-ish years) sis, but she is one of her closest pals, and was there for her during the early days of her motherhood journey. If Paula's in the movie, Melanie has to be. Liana Liberato has a Ciccone feel and looks like the confidante type. Joe Henry, Melanie's singer-songwriter hubby, with whom Madonna has collaborated, could also pop up.

The Rest

Madonna's other sibs (Martin Ciccone, Anthony Ciccone, Mario Ciccone and Jennifer Ciccone) may or may not be seen. Martin might warrant a mention. Her kids (Lourdes Lola Leon, Rocco Ritchie, David Banda Ritchie, Mercy James Ciccone Estere Ciccone and Stella Ciccone) are not likely to be seen except toward the very end, so as fun as it would be to cast them (maybe Paris Jackson as Lola in a cameo?), perhaps it's best to leave them be.

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All the Lovers (Sorry, Kylie)

Kelvin-harrison-jr-boycultureHarrison Jr. & Basquiat (Images via Entertainment & unknown)

Jean-Michael Basquiat — Kelvin Harrison Jr.

Madonna's even got her BF Ahlamalik hyping Basquiat, and her association with the tragic artist gives her street cred, art cred and was just absolutely, by all accounts, compelling and dramatic. He destroyed works he had given her when they broke up — that's how passionate things got. Basquiat will be in this movie — bet on it. I would love for an actor as gifted as Kelvin Harrison Jr. (Luce!) to play the troubled artist, who died while Madonna was just beginning to live.

0_0_3478042_02_1024x640This casting ... just, no. (Image via Amazon Prime)

Just please do a better job than the bizarre Amazon Prime flick Madonna & Basquiat (2019) did when it came to casting. Yikes!!!

Chase stokesBenitez & Stokes (Images via Netflix, personal photo & Atlantic Records)

Jellybean Benitez — Chase Stokes

I'm going with Outer Banks star Chase Stokes, even if it might be a bit of hair casting going on. Jellybean was a dish back in the day, and while much shorter than Stokes, I think Stokes might be great as her “shitty ex-boyfriend” ... who nonetheless gave us “Holiday”!

Ryan-jamaal-swain-boycultureSwain & Prince (Images via IG & Rolling Stone)

Prince — Ryan Jamaal Swain

Nobody immediately suggests themselves as Prince, a rather odd and unique character IRL, but I think Ryan Jamaal Swain could really summon the pervy depths of pre-Jehovah's Witness Prince, and he for sure has the sex appeal. It would be a nice stretch from his sweet-natured Pose performance, and I don't think hiring more than one Pose-er is a bad thing — Pose did Madonna a solid with its respectful re-telling of the saga of “Vogue.” Plus, it would be very Madonna to cast a gay man to play a ... whatever-Prince-was man.

Jonathan-tucker-boycultureTucker & the Poison Penns (Images via Audience & People)

Sean Penn — Jonathan Tucker

Sean ... Sean. This guy is bound to play a huge part of the Madonna movie, so the casting must be right. I think I've nailed it with Tucker, whose sexy intensity would fit nicely over Sean's. Also, please, Madonna, please: Recreate your disastrous wedding, complete with helicopters and Cher (Nadya Ginsburg!) in a purple fright wig. You can even include the funny Tom Cruise (Jacob Elordi!) story of him escaping the paps by clambering into a limo with a bunch of gay men and one very receptive wedding guest.

JFK-Jr-Theo-James-boycultureKennedy & James (Images via video still & Lionsgate)

JFK Jr. — Theo James

Madonna's fling with JFK Jr. was fast and furious, but I always had the impression maybe there was a lot more there there than she publicly let on. It came during her tumultous entanglement with Sean Penn, and included, reportedly, a meeting with his mom Jackie O, who definitely did attend Speed-the-Plow to check out her future no-way-she'll-be-my-daughter-in-law's acting chops. Theo James should be in everything anyway.

Pietro-boselli-boycultureBoselli & Ward (Images via IG & In Touch for Men)

Tony Ward — Pietro Boselli

Look, Tony Ward had a very Italian, sexy, masculine face, and it's going to be hard to match that. Instead, I suggest — since God forbid he receive more than glancing inclusion — casting a similarly hot male model. Pietro Boselli is a little bit of stunt casting, but imagine how great he will look on Madonna's arm. Plus, there can be a juicy scene where Madonna is pouting once she finds out that he's posed in gay magazines, only to have Liz Rosenberg say, “You're surprised? With that tush?”

Patrick-dempsey-boycultureDempsey & Beatty (Images via CBS & Disney)

Warren Beatty — Patrick Dempsey

Patrick Dempsey would be a great mid-life Warren Beatty! He was a pretty-boy actor who has matured into McDreaminess, and is close to (actually, a bit over) the age Beatty was during the Dick Tracy era. Bizarre how old Warren seemed to Madonna's fans. She was over 30, he was just over 50. Who cares?!

Justin-bieber-boycultureIce & Bieber (Images via NBC & Joe Termini)

Vanilla Ice — Justin Bieber

Hopefully, Vanilla Ice is not given much screen time in Madonna's biopic, but how fun would it be to see Bieber hamming it up during a Sex book romp? He'd probably have to pray on whether to do such a part, as Ice should have prayed on whether to let Madonna arrange to have photos made of him sexing her.

Tupac-shakur-boycultureShakur & Silver (Images via Columbia & IG)

Tupac Shakur — Steven Silver

I just caught the impressive Steven Silver in The Obituary of Tunde Johnson (a must-see), and I just bet he would be a dream as Tupac Shakur. Madonna is very proud of her relationship with the slain rapper, and protective enough of it she has sued over leaked letters that were set to be auctioned. (She lost.) He'll be in the movie.

A12f2fd24a203b27f968f94eb1cc4a96Boneta & Leon (Images via The CW & New Idea tear sheet)

Carlos Leon — Diego Boneta

I had a hard time with Carlos because he was a pretty face, but more than just that — and was often strong and silent beside Madonna. They broke up amicably and have co-parented Lola with great care. Diego Boneta is a good combo of pretty and empathetic.

Alex-pettyfer-boycutlurePettyfer & Ritchie (Images via IG & video still)

Guy Ritchie — Alex Pettyfer

Guy Ritchie and Madonna had a strong, then a weak, then a mutually draining marriage, one that ended so bitterly she seemed forever broken by it. You better best believe he will be represented in any life story of hers, and probably not flatteringly. Alex Pettyfer would be the perfect guy to act out Ritchie's laddish excesses, and who won't be waiting for the friction between Guy and Madonna's bro Christopher, who publicly called him homophobic?

The Rest

Influential downtown graffiti artist Futura 2000, one who Madonna enjoyed a positive relationship post-coitus; Norris Burroughs, the guy who quoted Madonna as craving his Brando body; Steve Neumann, who was the owner and publisher of Island, which gave Madonna her first-ever full magazine cover — and a gorgeous one at that; Bobby Brown ... yeah, she reportedly slept with him many years before Whitney, while, er, opening for New Edition; full-service bodyguard Jimmy Albright; turncoat Dennis Rodman; club owner John Enos; caddish Andy Bird; beautiful and kind Jesus Luz; treacherous Brahim Zaibat; and current lover Ahlamalik Williams.

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The Photographers

Steven meisel boycultureGarfield & Meisel (Images via Marvel & video still)

Steven Meisel — Andrew Garfield, Herb Ritts — Joseph Gordon Levitt, Steven Klein — Adam Driver

Madonna has been photographed by almost all the best, most legendary photographers of the era (Bruce Weber, Annie Leibovitz), but, with all due respect to such great shooters as Pierre et Gilles, Mert + Marcus, Patrick Demarchelier, Bettina Rheims and countless more, the only three photographers who stand a real chance of being depicted in meaningful ways are her stalwarts.

First came Meisel, who people sometimes forget preceded Herb Ritts by virtue of shooting her first promo poster, even though his work with her peaked in 1990-1992, culminating in the Sex book. I'd love to see an Andrew Garfield take on Meisel, and he's got the browline, home-grown!

Joseph gordon levitt herb rittsLevitt & Ritts (Images via EndGame Entertainment & video still)

Next was Madonna's most iconic photographer-collaborator, Ritts, who first shot her for the Desperately Seeking Susan movie poster, and soon after became her shutterbug of choice. They made so many iconic images together, it would be a shame if he were not included. I see Joseph Gordon Levitt — full-stop.

Cillian murphy boycultureMurphy & Klein (Images via video still & Matthew Rettenmund)

Finally, Madonna's latter-day closest photographer buddy is clearly Steven Klein. He's shot her countless times, and she socializes with him in a way she hasn't with any other creative partner. Cillian Murphy might be just the ticket for this offbeat visionary.

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The Handlers

Freddy-demann-boycultureDeMann & David (Images via Say It Forward & HBO)

Freddy DeMann — Larry David

Madonna and Larry David had crazy chemistry on an episode of the dearly departed series The Marriage Ref (2010), and I think he'd be a riot as her early-years manager, the man she sought out because he managed Michael Jackson. Joe Pesci crossed my mind, but he'd be more like Freddy now, rather than Freddy 35 years ago.

Elizabeth banks boycultureBanks & Rosenberg (Images via selfie & personal photo)

Liz Rosenberg — Elizabeth Banks

If Liz Rosenberg, Madonna's longtime publicist, doesn't make the cut for this film, we're through, Madonna. Liz is such an essential element of Madonna's career it was hard for me to pin down who could possibly play her. (Madonna did an outlandish parody on SNL — remember?) Ultimately, I think Elizabeth Banks would be like buttah. I think she could inhabit Liz's space and bring out the fact that Liz is sharp, loyal and quite taken with Madonna. I always loved that about Liz in the early years — she believed the hype, she didn't fake it. She was no-nonsense when it came to business matters, but also an extremely witty woman. Now retired from Madonna, Inc., it would be nice to have her back for a few minutes via this film.

Sacha-baron-cohen-boyculture-guy-oseary-madonnaCohen & Oseary (Images via video still & Matthew Rettenmund)

Guy Oseary — Sacha Baron Cohen

This one is so tough because Guy came onto the scene when he was extremely young, and might be portrayed at various points of her career. That said, I have always seen a Cohen vibe, depending on how meaty a portion of her life story he is afforded, as Cohen will not do a mere walk-on ... unless he feels beholden to Madonna for immortalizing him in her “Music” video.

Kristen-bell-boycultureZambreno & Bell (Images via selfie & video still)

Sara Zambreno — Kristen Bell

Zambreno is an unknown quantity, except to fans, so casting her is easier. As vital as she is to Madonna's life and work, as she has been for years, she's adept at keeping a low profile, so may not pop up in the movie — even though she's an executive producer. If the movie were to have any sort of focus on the circus that takes place behind the scenes that fans never see, I see an actor like Kristen Bell being able to handle coming off as in control but perhaps having private WTF?! moments.

Kathy-bates-boyculture(Images via selfie, headshot & New York Social Diary)

Liz Smith & Denis Ferrara — Kathy Bates & Jake Borelli

She was not a handler, but even though Liz was a member of the press, she stumped for Madonna like Lindsey Graham for Trump, cheerleading her from way back, and did it with the encouragement of the ultimate discerning fan, her longtime — nearly lifetime — right-hand man/co-writer Denis Ferrara. Denis, a fan's fan who cut his teeth on the likes of Marilyn Monroe and Elizabeth Taylor, IDed Madonna early on as the real deal, and the feeling was mutual. Kathy Bates would be a hoot as the glass-closeted Smith, and I favor bubbly Jake Borelli as Ferrara; I think he has the right mixture of pep and sarcasm.

The Early Influences

Neil patrick-harris-boycultureHarris & Flynn (Images via video still)

Christopher Flynn — Neil Patrick Harris

Having already endured being in The Next Best Thing with Madonna, Neil Patrick Harris might be over Madonna vehicles, even ones she's driving, but we need to start a movement to get Madonna's important gay dance teacher Christopher Flynn into this movie. He told her she was beautiful and helped her dare to dream, and I think Harris's gravitas and warmth would hit the spot.

SourceDion (GIF via GIPHY)

Ondine Massot — Céline Dion

This teacher from Madon 223b430d5942f21f54570e2999c2096ana's Michigan days had a strangely intimate relationship with the 15-year-old, letting her wear her tube top and kissing her on the lips for a photo. They also exchanged letters for years. Sadly, Massot died of cancer some time ago, but while I do doubt she will be portrayed, it would be a nice bit for the maternal Céline, no? Yes.

The Rest

Russell Long (who took Madonna's virginity), Sharon Maczko (a high school pal), Nancy Ryan Mitchel (Madonna's high school guidance counselor), Marilyn Fellows (Madonna's favorite high school teacher) and Whitley Setrakian (Madonna's college-era roommate, who later published a book on the experience) are others from this era to consider.

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Emmy / Breakfast Club / Solo

Tyler-james-williams-boycultureWilliams & Bray (Images via CBS & personal photo)

Stephen Bray — Tyler James Williams

Madonna knew Bray in Michigan and was in bands with him in NYC, including Breakfast Club. More importantly, he co-wrote and produced some of her most memorable hits, including “Angel,” “Into the Groove,” “Causing a Commotion,” “Keep It Together” and the masterpiece “Express Yourself.” I think Tyler James Williams is a direct hit, so to speak.

Tom hollandboycultureHolland & Gilroy (Images via video still & IG)

Dan Gilroy — Tom Holland

One of Madonna's most important contacts, a boyfriend who encouraged her to explore her singer-songwriter impulses. He was profusely thanked when she achieved Rock and Roll Hall of Fame status, though he seems to have fallen from favor for airing some of their private recordings. He absolutely has to be in the movie, and portrayed sensitively. Perhaps it is wishful thinking that Spider-Man himself would deign to play a Madonna discard, but I think it could be a tremendously substantive role, if Madonna gives Gilroy a full airing.

Teri-hatcher-boycultureHatcher & Barbone (Images via IG & handout)

Camille Barbone — Teri Hatcher

I like the idea of casting Teri Hatcher against type as butch goddess Camille Barbone, for whom Madonna was the act (and the girl?) who got away.

Patrick-hernandez-boycultureHernandez & Styles (Images via video still & personal photo)

Patrick Hernandez

Disco singer Patrick Hernandez was already nearly over the hill (at, like, 30) when he had Madonna in his backing troupe for a hot second in the very early '80s. It's a bizarre time in her life, Madonna's trip to France to become a stahhhr, and one that I'm sure most fans would welcome hearing more about. I want someone gimmicky and fun in this role, and can think of nobody I'd rather see performing “Born to Be Alive” than Harry Styles.

The Rest

Emmy bandmates Vinny (something), Mike Monahan and Brian Symmes; Breakfast Clubbers Gary Burker, Ed Gilroy and Angie Smith; Barbone's right-hand man Adam Alter; and Jean Vanloo and Jean-Claude Pellerin, the scouts who took Madonna to France.

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Early NYC Days/Downtown

Wendie-malick-boycultureGraham & Malick (Images via Wikipedia & CBS)

Martha Graham — Wendie Malick

Don't pretend you can't see it. Also, we need to cast Graham because if Amy Pascal told Madonna the movie could only be 90 seconds long, it would contain a scene of Graham confronting her in the halls of her dance school and dubbing Madonna Madame X. Also, we as fans need to try to get an actor who appeared in Madonna: Innocence Lost (she played Camille Barbone) into this movie without Madonna realizing it.

Aisling franciosi boycultureFranciosi & Maripol (Images via BBC & Maripol)

Maripol — Aisling Franciosi

Maripol was a close confidante of Madonna's for years, and contributed so much to her style, particularly that iconic BOY TOY look, styling her first magazine cover, the Like a Virgin album cover and so much more. They remained friends and in touch for many years, so I'd love to see her in the movie. Aisling Franciosi has the right look. I can see her as the provocative artist Maripol, and as the intimate friend.

Edo bertoglio boycultureChalamett & Bertoglio (Images via IG & Edo Bertolgio)

Edo Bertoglio — Timothée Chalamet

Timothée dated Lola in real life, so I don't think he would be in a Madonna biopic. But he might be suitable for Edo Bertoglio, Maripol's baby daddy and the photographer who shot her first, abandoned album cover since Edo wouldn't be in it very long. A cameo?

Screen Shot 2020-09-16 at 4.08.32 PMSivan & Burgoyne & Dorfman (Images via selfies & personal photo)

Martin Burgoyne — Troye Sivan or Tommy Dorfman

Martin deserves to be in Madonna's biopic. Her very best friend in her early years in NYC, they traveled to London together (her first trip) and he was with her as she achieved some of her earliest successes, designing a 12" sleeve and working on her first album cover (which was tossed in favor of a different approach). He died of AIDS, and his death — like Keith Haring's — galvanized Madonna in the war on AIDS. I think Troye would do nicely here, though Martin had a real edge (he liked leather and SM), so I am also open to Tommy Dorfman ... and may even be open to suggestions like George MacKay or Ross Lynch.

Debi-mazar-gillies-boycultureMazar & Gillies (Images via personal photos & selfie)

Debi Mazar — Liz Gillies

I think the former Nickelodeon star is a terrific actress, has a Debi delivery ready to go and her brow game never falls short. I think this one is perfect.

Keith-haring-boycultureWright & Haring (Images via video still & NYDN Magazine)

Keith Haring — Isaac Hempstead Wright

I have to believe that Keith Haring will be an essential, even pivotal figure in the film. Casting him is important, as he needs to be dorkily cute have have an impish quality. He is also a person who very closely shared Madonna's own urges — to get famous, to express oneself, to use the resulting notoriety and money for good. Isaac Hempstead Wright, 21, strikes me as a good fit.

Tilda-swinton-boycultureSwinton (Image via Interview)

Andy Warhol — Tilda Swinton

Madonna's artistry and the swath she has cut through popular culture are often misread, as is her offputting sense of humor. It's because she is the last of the Warhol babies. She is far more interested in boundaries than earning an EGOT (though she'd happily take it, and deserves more than a few grudging Gs). That said, and while she definitely interacted with Warhol, I could see him appearing more ethereally. As such, it's unlikely anyone terribly famous would play him, unless it were as a wink. And if as a wink, who better than Tilda?

The Rest

Pearl Lang, another of Madonna's biggest dance influences; Studio 54 owner Steve Rubell; fellow artiste Grace Jones; Streisand's partner Cis Corman, who sent Madonna to Scorsese for The Last Temptation of Christ; Corman's son Richard, who shot memorable early-years images of Madonna; Michael Musto, the gossip king who once shared a dressing room with Madonna when he was in a band; ubiquitous downtown presence Haoui Montaug, who introduced Madonna's now-legendary early performance of “Everybody” at No Entiendes once she was signed to Sire; Boy George, because Madonna was scared of his cool bitchiness when she met him on her first London trip; and even Barbra Streisand, who first met Madonna at a Chinese restaurant with her then-boyfriend Jon Peters, who wanted to chat with Madonna about Vision Quest (1985). Streisand found it presumptuous that Madonna ordered a whole fish on Peters's dime. Imagine this scene! Plus, how crazy that the premier woman singer-actress-director was meeting with a future icon in the same mold so early on. (I didn't cast her because I'm unsure Madonna would even focus on such an encounter, but ... Gaga, are you free?)

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The Nude Photo Flap

Hugh Hefner — Bryan Cranston

Bryan-cranston-sean-penn-boycultureGuccione Jr./Penn, Cranston/Hefner (Images via video still, selfie, HBO & historical photo)

Bob Guccione Jr. — Sean Penn

It would be delicious to see Bryan Cranston as the sophisticated sleaze whose issue of Playboy with Madonna's early-years nudes was in a race with rival Penthouse's batch of nudes, and considering the fact that Guccione sent copies of Penthouse to Penn in prison to get his goat, seeing Penn breathe life into that creep could be the one bit of stunt casting I would tolerate.

The Rest

The men who shot Madonna in the raw when she was a nobody, Martin H.M. Schreiber and/or Lee Friedlander, and who made at least six figures if not more once she became a household name, would probably just be shown as shadowy figures behind cameras.

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A Certain Sacrifice

Evan-peters-boycultureLewicki & Peters (Images via video still & Netflix)

Stephen Jon Lewicki — Evan Peters

Madonna so desperately wanted to win a part in the no-budget film A Certain Sacrifice, she wrote a long letter to its creator, Stephen Jon Lewicki. She was less than pleased with the results, a hard-to-watch movie with a prurient rape sequence. When it was marketed by Lewicki during her initial burst of fame, she sued him — and lost. He made a mint. Evan Peters would be great, and he comes highly recommended by Ryan Murphy.

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Madonna (album)

Penn-badgley-boycultureBadgley & Kamins (Images via Netflix & personal photo)

Mark Kamins

Kamins is the DJ with whom Madonna was involved romantically, and who took her demo to Sire, which directly led to her recording contract. He wasn't able to produce the album, as he had hoped, instead getting nudged out in favor of more experienced producers. Still, he is an essential element of Madonna's recording career, and she acknowledged him when he died in 2013. Penn Badgley is an actor who would, I think, adapt nicely to a downtown milieu; I would love to see his take on a DJ who discovers the next big thing, only to benefit from that discovery so little.

Mike-myers-boycultureStein & Myers (Image via video still & selfie)

Seymour Stein — Mike Myers

Let's face facts: There is a 0% chance that a Madonna biopic will come and go without a dramatization of Madonna meeting Sire honcho Seymour Stein in his hospital room as he recovers from surgery, seizing a contract by sheer force of will. I would like to see a master of disguises like Mike Myers as Stein. Perhaps she can call in that Austin Powers favor.

Bagz-rilez-boycultureRilez & Williams (Images via Kiri Teshigahara & selfie)

Bagz Rilez — Ahlamalik Williams

Madonna never so much as talks about Bagz, but he could pop up in early track dates, and it would be a cute moment to give a hat-tip to her latest love, Ahlamalik Williams, who I'm almost sure will not warrant inclusion in the story. No biopic is going to end with Madonna sitting at home surrounded by her loved ones and saying out loud, “I'm so content!”

Letitia-wright-erika-belle-boycultureWright & Belle (Images via THR & IG)

Erika Belle — Letitia Wright

Whether Madonna remembers it or not, Erika Belle was a huge part of her formative years as an artist, and contributed greatly to some of her early, iconic styling. Belle remains a supporter, and deserves to be seen, so I'm shooting for the stars by casting super hot Wright.


Mary Lambert

Mary Lambert is the woman who gave us several of Madonna's most classic music videos, including “Borderline,” “Like a Virgin,” “Material Girl,” “La Isla Bonita” and “Like a Prayer.” She worked well with Madonna, and there could be a nice beat to be mined exploring how Madonna fared when paired with a creative woman. Speak of the devil, Chloë Sevigny would bring such gravitas and quirkiness to the part — hire her!

The Rest

Michael Rosenblatt is the Sire suit who connected Madonna with Seymour Stein; Reggie Lucas and Arthur Baker are first-album production figures; Ed Steinberg is the man who directed Madonna's first, rudimentary music video; Kenny Compton is the hot piece of ass (who Madonna was dating) whose cheekbones enliven her “Burning Up” music video, directed by Steve Barron; Arthur Pierson directed “Lucky Star,” which, of all her early videos, feels like something the movie might try to capture.

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American Bandstand

Greg-kinnear-boycultureClark & Kinnear (Images via video still & Marc Maron)

Dick Clark — Greg Kinnear

Name a more iconic TV moment for young Madonna than her 1984 American Bandstand debut, on which she declared she wanted to rule the world. I'll wait. Meanwhile: Greg Kinnear would be a perfect Dick Clark, since Ryan Seacrest would be a little too on the money.

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Like a Virgin

Michael-b-jordan-boycultureJordan & Rogers (Images via Marvel & fan photo)

Nile Rodgers — Michael B. Jordan

Nile Rodgers was already a legend when he met Madonna, and they worked together very well, cooking up the classic album Like a Virgin and maturing her sound. He has since spoken very positively of Madonna's musicality. I think he warrants inclusion, and Michael B. Jordan could portray Nile's intellect and effortless cool.

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Virgin Tour

Josh-peck-boycultureLeonard & Peck (Images via clipping & selfie)

Pat Leonard — Josh Peck

Madonna's songwriting association with Pat Leonard (“Like a Prayer,” among many others and across the '80s, '90s and '00s) began on this tour. If she does, as she has said, include the genesis of “Like a Prayer,” Leonard will make the cut. I think someone capable of playing a silent creative partner is called for, and this is as good a place as any to use the always-great Josh Peck.

The Rest

Madonna's costumer was Marlene Stewart; her dancers were Michael Perea and Lyndon B. Johnson; her sexy guitarist Paul Pesco was quite an attention-grabber; and of course her opening act, the Beastie Boys, would also be amusing to see on film.

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Desperately Seeking Susan

Alison brie-boycultureBrie, Seidelman & Arquette, Debicki (Images via Netflix & 20th Century Fox)

Susan Seidelman — Alison Brie, Rosanna Arquette — Elizabeth Debicki

Madonna has not given enough attention to the role Desperately Seeking Susan played in her early career. True enough, she was already a major star once Like a Virgin came out, but the movie — the Madonna Movie — amped things up. On top of that, she was excellent in it, it was a completely woman-powered (executive, producers, director, writers, stars) venture, and it's a great film that withstands the test of time. I'd like to see Alison Brie as indomitable Susan Seidelman, the film's director, and maybe Elizabeth Debicki as Rosanna Arquette. Madonna and Rosanna were close during filming; there could be more story there.

The Rest

I'm not sure which, if any, of her DSS cast mates would be shown, but for the sake of being complete, they include (but are not limited to) Aidan Quinn, Laurie Metcalf, Mark Blum and Robert Joy. A bit of celebrity writer Mark Bego interviewing Madonna on the set could help set up how momentously her fame exploded just from the time filming began until it ended (she did the MTV Awards in 1984 during the shoot).

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True Blue

The Rest

Nobody jumps out as a must-include, but people from this era who could appear include director Jean-Baptiste Mondino (Felix Howard starring with Madonna in his “Open Your Heart” video); Danny Aiello and Alex McArthur from “Papa Don't Preach”; and, later, Chris Finch from the Who's That Girl Tour.

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Shanghai Surprise

George-harrison-boycultureHarrison & Bale (Images via People & selfie)

George Harrison — Christian Bale

Madonna might have her mind set on covering her contentious time filming this turkey for ex-Beatle George Harrison with Sean Penn. If so, good luck getting Christian Bale, but he kinda favors George already and wound up a dead ringer for Dick Cheney in Vice post-makeup and Whopper binges, so would likely be able to fool George's kin once filming commenced.

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Who's That Girl (movie)

The Rest

Perhaps director James Foley will be included, or co-star Griffin Dunne? Fans like this movie, even if it bombed way back when, and it's not even close to her worst effort.

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Speed-the-Plow / 1988

David-mamet-boycultureMamet & Brolin (Images via vintage head shot & mug shot)

David Mamet — Josh Brolin

Gosh, it seems like her time on Broadway could be covered since she loathed it, and called Mamet a woman-hater. Maybe a he-man like Josh Brolin could fill the bill. Yes, I used his mug shot.

The Rest

Ron Silver and Joe Mantegna were in the play with Madonna.

Abby-wilde-boycultureWilde & Bernhard (Images via social media & video still)

Sandra Bernhard — Abby Wilde

Nobody quite looks like Sandy. She is unique, and her physicality is part of what made her shine in The King of Comedy (1982) and on the concert stage. That said, Nickelodeon actor Abby Wilde (now 31, the right age for when Bernhard was palling around with Madonna) could potentially evoke her. She also sings, as does Bernhard. It is essential that Bernhard be a part of the Madonna story, if only for a re-do of Madonna's first Letterman appearance, and for their bitter falling out over Ingrid Casares. If Bernhard is not in the movie, then get me a Rémy Martin with a water back, god damn it!

The Rest

Jennifer Grey could round out the notorious Snatch Batch!

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Like a Prayer

Matthew-gray-gubler-boycultureFincher & Gray Gubler(Images via Joanne Gair & CBS)

David Fincher — Matthew Gray Gubler

Fincher  directed  some of Madonna's best videos, and is now an A-list director, so Madonna may take those things into consideration when deciding if he merits a mention. I like Criminal Minds actor Matthew Gray Gubler here. Oh, brother? Oh, father.

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The Oscars

Madonna-michael-jackson-keiynan-lonsdale-boycultureThe oddest couple & Lonsdale (Images via People & selfie)

Michael Jackson — Keiynan Lonsdale

No way in hell Madonna won't include any aspects of her odd association with Michael Jackson. The one-sided friendship (he seemed to disparage her as a heifer in private, and to be jealous that people would compare their statuses, she was thrilled to be in his league and respectful of his talent, if not his dress sense) and their jaw-dropping Oscars date must be plumbed. I am going with Keiynan Lonsdale (he would be 29+ at the time of filming, and Jackson was 32 at those Oscars) as a perfect Jackson replica, both physically similar and somehow possessing an otherworldly charm, too.

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José Gutierez — Jason A. Rodriquez

Hey, it's not a huge stretch to cast Rodriquez, who works with José on Pose, but we want someone who looks right and can vogue for days. He deserves to break out a little more than he does on the show, and being in one of the biopic's biggest scenes would hit the spot.


75e2114817b5f53f4a41a27bcfe0b2ccAbove: José & Luis (GIFs via GIPHY)

Luis Camacho — Diego Tinoco

I don't think Luis will object too strenuously here! Beauty's where you found it and (checks notes) I found it!!! I think Diego, a rising-star Latinx actor, would look great as Luis, and I'd love to find out if he can dance — wouldn't you?

Diego-tinoco-boycultureTinoco (Image via IG)

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Dick Tracy & I'm Breathless

The Rest

I mean, aside from Warren Beatty, I'm not sure we need much from Mandy Patinkin, or even Stephen Sondheim.

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Blond Ambition Tour

LxztryDDonna & Niki (GIF via GIPHY)

Donna De Lory & Niki Haris — Laura Marano & Danielle Brooks

It's important to get these right-on women right-on, and I think I have. I like former Disney Channel star (and boss singer) Laura Marano as Donna, the girl who can sound more like Madonna than Madonna, and I like Danielle Brooks for Niki.

Screen Shot 2020-09-16 at 8.56.32 PMMarano & Brooks (Images via Twitter & IG)

Laura is far more the spitting image of Donna than Danielle is Niki, but I love Danielle, I hang on her every word, and we need a powerful presence to be able to push back against Madonna's plans for burning crosses in her “Like a Prayer” video, someone who looks up to Madonna — but is able to stand her ground when she isn't into the ride.

GaultierGaultier & Dujardin (Images via French Glamour & IMDb)

Jean-Paul Gaultier — Jean Dujardin

Gaultier was one of Madonna's all-time most impactful co-creators, from the cone bra (whose invention and application promises to figure into the movie) right up through her Met gig. I realize Jean Dujardin is about 10 years older than Gaultier was in 1990, but I think the Oscar winner would be a trip as the fashion genius.

The Rest

José & Luis were taken care of in my vogueing section. I have no doubt that Madonna's full Blond Ambition troup — Salim Slam Gauwloos, Kevin Stea, Oliver Crumes, Gabriel Trupin, Carlton Wilborn, Mama Makeup (Rebel Wilson?) and choreographer Vincent Paterson — will be seen, but I don't think they'll have substantial characterization. I could be wrong, especially since some of them later sued her, a score she may wish to settle. Pedro Almodóvar recently bitched about an encounter he had with Madonna on film during the tour's stop in Spain, a sequence in Truth or Dare that included Antonio Banderas (see below). She gave a memorable interview to Arsenio Hall, and she of course had some controversies on this tour — Kevin Costner, anyone? Perhaps Pope John Paul II? Kurt Loder?

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The Immaculate Collection

KravitzKravitz ... recently! (Image via social media)

Lenny Kravitz — As Himself

Here's hoping they don't restage Madonna's “Ray of Light” performance from MTV (yikes), but Kravitz was around for “Justify My Love,” and is a longtime pal. I think he should play himself — he looks the same!

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Truth or Dare

26TRUTHORDARE3-web-jumboKeshishian & Sevani (Images via Miramax & Touchstone)

Alek Keshishian — Adam G. Sevani

The director of Truth or Dare went on to become a close friend of Madonna's, and later helped her flesh out W.E. He is likely to be seen during the 1991 era. I thought of Sevani immediately. Maybe it's an Armenian thing, but I think he would be fun.

Garlin-boycultureWeinstein & Garlin (Image via NYP & HBO)

Harvey Weinstein — Jeff Garlin

Madonna worked with Weinstein on this and W.E., and was around him often. She later exulted in his demise, so may have untold stories to tell. I think the casting is self-explanatory.

The Rest

Moira McPharlin, so fun in the movie, could be Kristen Wiig, but other than that ... ! Don't forget Madonna gave a juicy interview to the late Carrie Fisher, and that the late Regis Philbin conducted a black-and-white interview with the siren in Hollywood, both possible set pieces. Around this time, Madonna became a patron of the art of Lypsinka, so maybe Violet Chachki will get a call. (And if Madonna calls, don't be like Junior Vasquez, who will most certainly not be in the movie, and refuse to pick up!) And how about a peak at Camille Paglia, just so Madonna can roll her eyes at her?

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A League of Their Own

Julie-goldman-madonna-rosie-odonnellGoldman & O'Donnell (Images via IG & Columbia)

Rosie O'Donnell — Julie Goldman

Madonna made a bosom bosom buddy for life on A League of Their Own in O'Donnell, and lesbian comic actress Julie Goldman could knock this one right out of the ballpark.

Dratch-boycultureMarshall & Dratch (Images via Columbia & video still)

Penny Marshall — Rachel Dratch

Come on, I want someone as funny as Penny to play Penny, and Dratch would make that happen.

Tom hanks boycultureThe Hankses (Images via Columbia & selfie)

Tom Hanks — Colin Hanks

I mean, obviously.

The Rest

Geena Davis, Lori Petty and Eddie Mekka (Mark Ballas?) are also prominently in ALOTO, and Madonna dances up a storm with the latter.

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Ana de armasCasares & de Armas(Images via National Enquirer & Ben Affleck)

Ingrid Casares — Ana de Armas

The one must-have for this era is Ingrid, who became one of Madonna's best friends after she allegedly stole her from Sandra Bernhard, ruining that friendship. Perhaps Madonna will reveal whether she and Ingrid really were romantically involved after all? Madonna will want a big name to play Ingrid ... so howzabout Ana de Armas? Haircut required; no wigs.

The Rest

Naomi Campbell could be glimpsed, considering Madonna shrimped her! Glenn O'Brien wrote the book with Madonna, and was a longtime downtown cohort; Fabien Baron designed it; and porn star Joey Stefano and stripper Rocky Santiago are among the most eye-popping participants in the book ... will we see Madonna getting her freak on (it's a 1992-appropriate reference!) in the notorious Gaiety?!

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Erotica Era

David-harbour-boycultureHarbour & Pettibone (Images via head shot & personal photo)

Shep Pettibone — David Harbour

For many fans, Madonna's Erotica was one of her finest albums, sorely underrated. Her maestro, Shep Pettibone, had helped her create “Vogue” and here participated in one of her most liberating expeditions. I was thinking David Harbour (he's a bit older than Shep was), and then remembered she hired him for W.E., too. Robert Pattinson is my backup.

The Rest

Tony Shimkin was famously a part of the recording sessions; Udo Kier, Sofia Coppola and Christopher Walken all appear in Erotica-era music videos; Madonna met chanteuse Peggy Lee around this time; and she soon after performed on both SNL (with Roseanne Barr!) and with Anthony Kiedis for Arsenio Hall's 1,000th show. Depending on how long this era is defined, we also have Body of Evidence (Willem Dafoe!) and Dangerous Game (Abel Ferrera battles) in the mix.

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The Girlie Show

The Rest

Will we see a topless actress impersonating Carrie Ann Inaba? Witness Madonna firing a fading Gene Kelly? Will this tour even be mentioned? Alanis Morisette, Madonna's big Maverick success, also exists around this general period. Maverick might be included since it would be a nice point of interest on her path to gaining control.

The Late Show with David Letterman

Boyculture-marc-maron-david-letterman-mel-brooksMaron & Letterman (Image via CBS)

David Letterman — Marc Maron

I think we'll all fucking ask for our fucking money back if we don't see fucking Madonna nearly fucking self-destruct out of pure fucking spite on David Letterman's fucking show. Maron could fucking do Letterman in his sleep.

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Bedtime Stories

The Rest

Of Madonna's BS-era collabs, Babyface is the one with the most oomph, but I'm not sure Bedtime Stories will even rate, quite honestly. If it does, look for Björk, Dallas Austin, Dave Hall, Nellee Hooper, Mark Romanek and Meshell Ndegeocello, all of whom exist in this era.

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MTV Video Music Awards (1995)

SnIP TwM5AUVLove & Momsen (GIFs via GIPHY)

Courtney Love — Taylor Momsen

Come on, we have to have the compact-throwing episode. It was emblematic of so much more than just a minor catfight. It was a great example of just one time when an artist attempted a changing of the guard against Madonna's will. Taylor, you were born for this one.

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Alan Parker — Stephen Fry, Antonio Banderas — Maxi Iglesias, Carlos Menem — Leonardo Sbaraglia  

Evita will for sure be well-documented in Madonna's story (she's promised as much) — it is a turning point in her life (she was pregnant with Lola during the filming) and career (it nearly dragged her into an Oscar nomination).

Stephen fry-boycultureParker & Fry (Images via Hollywood & video still)

The late Alan Parker could be well-represented by former Madonna agnostic Stephen Fry (he trashed her in the early years).

Banderas-boycultureBanderas & Iglesias (Images via Hollywood & Amazon Prime)

I think sexy Antonio Banderas, who first crossed paths with Madonna in Truth or Dare, could be embodied by Maxi Iglesias.

Pain and glory boycultureSbaraglia & Menem (Images via Sony & Wikipedia)

And we almost certainly will get a scene with Madonna trying to persuade then-Argentinean President Carlos Menem to allow her onto his Casa Rosada balcony — let's try Pain & Glory star Leonardo Sbaraglia, who would be surprisingly good for this.

The Rest

Andrew Lloyd Webber (who wasn't very nice to Madonna), Tim Rice and Jonathan Pryce are in the mix.

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Boyculture william orbitOrbit & Merchant (Images via WEA & video still)

Ray of Light

William Orbit — Stephen Merchant

Orbit was the architect (along with other producers and, more importantly, Madonna) of Madonna's second-to-last greatest (so far!) musical comeback, a period of her career that was unique to her evolution as an artist. If music truly is guiding this movie, William Orbit will be in it. Stephen Merchant is incapable of fucking any part up. Let's go with him. Send out the contracts!

The Rest

Jonas Åkerlund, who went on to direct a number of her videos (and whose wife has styled Madonna), could rate.

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The Rest

I fear that Kabbalah could become a major plotpoint in Madonna's on-screen journey, as it has her off-screen journey. This could be one area in which directing her own story would be a blind spot, because I think most of her fans are unimpressed by how her spirituality has guided her. Nonetheless, if handled briskly, it could be effective. Perhaps the Bergs, the pushers of the faith, could appear.

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The Next Best Thing

The Rest

This movie was so disappointing and drove a wedge between Madonna and Rupert Everett — and a wedge between John Schlesinger and the Earth — that I'm thinking she will skip it altogether.

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Music (album)

The Rest

Music was a huge album for Madonna, and its lead single became her last (so far) #1 hit. It's one of her most iconic songs. And yet, I am at a loss for who from this era would make the cut, other than Monte Pittman or perhaps a Sacha Baron Cohen cameo.

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Drowned World Tour, American Life, Re-Invention Tour, Malawi, etc.

Bailee-madison-britney-spears-boycultureMadison & Spears (Images via selfie & Us)

Britney Spears — Bailee Madison

Of all of Madonna's biggest stunts and most iconic musical performances, the one that jumps out at me from post-2000 is Hollywood at the MTV VMAs, during which she kissed Britney Spears (and Christina Aguilera!). I can definitely see this being interpreted on the big screen, and if Bailee Madison is not Britney Spears reincarnated (RIP Britney), who is??? (And for Christina Aguilera, get anyone. It would be better to have it be an extra since that's how the media treated her in the aftermath.)

The Rest

Missy Elliott could be seen if the other girls are. Also, Nathan Rissman, who Madonna met when she was first becoming interested in Malawi, has a shot.

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Confessions on a Dance Floor/Confessions Tour

Dylan-minnette-stuart-price-boyculture-madonnaMinnette & Price (Images via Netflix & personal photo)

Stuart Price — Dylan Minnette

Minnette might be a tad young, but I think the story of how wunderkind Price helped Madonna get her groove back with Confessions on a Dance Floor can bear the age difference being widened. Price worked with Madonna much earlier, but this was the period in which he had his greatest impact. And in case you're wondering why I'm casting no one after the mid-2000s, career-wise, it's because in my head, ending with the triumph of Confessions, Madonna out onstage in peak form, showing them how it's done 25 years later, would be the way to go.

The Rest

If Daniel Cloud Campos is played by anybody, he better be fine as fuck. Nicki Richards could be included.

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Hard Candy/Sticky & Sweet Tour

The Rest

Madonna worked with Justin Timberlake, Timbaland, Pharrell Williams and Kanye West, among others, during this era. It led to her most successful tour, but nothing about this phase is must-see for the movie of her life. (Says me.)

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MDNA, Super Bowl, MDNA Tour, Grammys 2014, Rebel Heart, Rebel Heart Tour, Madame X, Madame X Tour, blah-blah-blah ...

The Rest

I firmly believe most of the latter-day Madonna people, places and things will not be overly represented — if at all —in the movie. But you never know, and since you never know, what about ... Nicki Minaj, Lil Buck (dancer), Marvin Gofin (dancer), Macklemore and the other Mary Lambert, Miley Cyrus, Taylor Swift, Avicii ... In the end, it's all about how Madonna frames the Madonna story.