Songwriting legend Patrick Leonard may not be a household name, but he's certainly a Madonna fan's household name.

She has worked with many brilliant collaborators, from Stephen Bray to Shep Pettibone to William Orbit, but it would be hard not to settle on Leonard as her most important, considering his work with her across three decades that produced a diversity of hit singles representing a huge part of her legacy.

And his own. ...

Patrick Leonard — he gave Madonna something to remember.

As he prepares for a September 12 show in NYC at Joe's Pub (with proceeds going to the VH1 Save the Music Foundation) in which he and a small band will play approximately eight of his classic Madonna co-creations and during which he will speak about his work with the Queen of Pop, Leonard — as forward-looking as his old boss — reflected on his motivation in a leisurely call with me last week. Saying the show is “me looking to embrace something that I didn’t really realize was, and this is in big quotes, a legacy for me,” he also humbly muses, “I always knew it was there, but I never considered it mine because it was never my picture on the album cover.”

Get Tickets for Leonard's NYC Show Here!

We owe a debt of gratitude to John D. Lee for the show, which is selling out. Leonard's daughter Jessica — she of “Dear Jessie” fame — is now a screenwriter, and Leonard connected with Lee, a film consultant who previously worked at the Tribeca Film Institute, via her. Lee, a longtime Madonna fan, was instrumental in helping make the show happen once Leonard — a latecomer to Instagram — realized there was such a demand.

Six of the 10 U.S. singles Leonard wrote with Madonna (Images via Warner Bros.)

He joined Instagram when Leonard's musician son Sean read a 2015 interview with Madonna in which she was asked about his dad. Part of her response was, “Pat Leonard? I mean, he might have an Instagram account, I don’t know.” Leonard laughed when he read that, but signed on, posting items related to artists he's worked with, like Leonard Cohen, Roger Waters and Madonna. Since it was right around the time he had moved his storage locker, he'd just found a cache of Madonna tapes and papers he hadn't seen in forever. Posting tantalizing tidbits elicited a hungry response.

“Suddenly, I had all these Madonna fans that started to hit me up and I realized that they were pretty into being able to see what there was and what I had and be in touch with me in whatever way, something I’d never really considered, not in all of these years,” he says.             

Shockingly, Leonard — referring to social media as “a bit of an awakening” — says he hadn't spent much time with his most famous songs from the time they were recorded 20 and 30 years ago until prepping for the NYC show over the past few weeks. “There’s some of these songs that I’m playing with a little bit now, just trying to find a way to play them, that I’ve haven't played since back when we recorded them,” he confirms, “which, there's a good chance is the only time I played it. Wrote it, recorded it and never played it again.”

We're talking about songs like “La Isla Bonita,” “Live to Tell,” “Who's That Girl,” “Like a Prayer,” “Cherish” and many more.

Speaking with him about his upcoming show, I was able to ask Leonard about Madonna's musical chops, the origin stories of their best-known works, how he feels about her many reinventions of their songs over the years, and just how many unreleased songs he’s got up his sleeve.

Madonna with Leonard's dad the day she first collaborated with Leonard (Image by Patrick Leonard)                                                             

Boy Culture: Madonna is basically anti-nostalgia, though she has warmed up to her back catalogue some in recent years. For you, what is it like looking back as you put together your show?

Patrick Leonard: I’m thrilled to go back and look at these things, and to look at what’s inside of the composition that I can mess with now so it feels like it’s something I’m doing presently and not just going back and playing through the chord chart from something that I wrote 30 years ago. The exploring of them is fun for me, but in terms of nostalgia or looking back — not really my way. I’m always looking for what I can do, not so much what’s new or different or anything like that, but I work almost every day. I’m still just looking for things.

BC: What can fans expect from your NYC show?

PL: It’s instrumental, so songs, no singing. But I feel like the songs have been sort of embedded in us over the years, so we only have to hear a hint of them and it’s like it turns on a switch and the song plays along with it. I used to hate when I’d go see a band and they’d change something, anything. It can piss you off. I’m gonna see if I can not piss people off. [Laughs]

BC: You've worked with Leonard Cohen, Robbie Robertson, Fleetwood Mac, Jeff Beck, Elton John [pictured] — Madonna sticks out on the rock-and-roll-oriented list. How did you come into her orbit? I know you worked on the Victory Tour for the Jacksons so was wondering if she, as a Michael Jackson admirer, sought you out?

PL: I had done the Victory Tour and quasi music-directed it. It wasn’t a formal title, but it turned out to be my job. When that tour was over, her (then) manager called my (then) manager and asked if I would be interested in putting her first tour together. I wasn’t initially, then we met and talked and I agreed to do it. The connection that we had ... we’re two completely different artistic spirits, we couldn’t be more different, and consequently when we did work together, there was a very interesting chemistry that's still palpable.

BC: You were brought on to do a small tour, but her Virgin Tour blew up quickly.

PL: The first show was in Seattle, I think it was a 2,000- or 2,500-seat proscenium theater, and I think there were 10,000 people outside and so it was the last theater we played. That’s what the tour was gonna be, it was gonna be 2,000-seaters, and it went from that to 10,000-seaters in a week. Nobody really knew. They didn’t realize how much people loved her. That was pretty cool to see.

BC: Did she come to you with set-in-stone ideas?

PL: In terms of staging and choreography and things, I had no say or no part of it and it wouldn’t be my place to say anything anyway. It was her first tour and she was really clear that she had never done it before and there would be very little pushback (musically). What I wanted to do was how it would get done. We did some really interesting things, like using emulators for background vocals that later on became much more common, but I don’t think anyone, at that point, had done it. She let me do the job. It was really nice to have that trust from her.

BC: Were you responsible for the Michael Jackson mashup?

PL: The “Billie Jean”/“Like a Virgin” thing, that was something that started as one of those musical anecdotes: If you play “Billie Jean” in a major key, it’s “Like a Virgin.” And so, having just done the Jackson tour, we started doing “Billie Jean”/“Like a Virgin” at the early, early rehearsals kind of just to wind her up and she dug it so it stuck. [Laughs]

Great Virgin Tour Scrapbook by Bill Lanphier Here!

BC: How did you come to write together?

PL: We got back from the tour and just kind of by accident wrote “Live to Tell.” I’d written some music for a film, trying to get a film score, and they didn’t hire me for the film, so in a 24-hour period it went from that film to At Close Range. Madonna had agreed, just as a favor, to write the lyrics for me because it would give me a leg up on getting this film score for her to write the lyrics to the end title, which was based on one of the themes that I was writing for this other movie. It became the score for At Close Range and “Live to Tell.”

“Love Makes the World Go Round” was our first song and then “Live to Tell” was the second song that we wrote.

BC: Wow, so your first-ever collaboration was “Love Makes the World Go Round” — the True Blue song she debuted at Live Aid. Did you write it on the road?

PL: My memory’s gonna be a little hazy around when we wrote what and people will probably correct it. Feel free, gang. We didn’t do a lot of writing on the road. “Love Makes the World Go Round,” I had a barbecue at my house and she came and I showed her the track. I think she wrote it right then and there, or else she took a cassette away. Can’t remember, honestly. I actually found that cassette the other day, too, the first song idea I ever handed her and the first thing we ever worked on. It wasn’t until after the tour that we wrote “Live to Tell” and that started the True Blue record and then we wrote whatever other songs we wrote together for True Blue.

BC: Your influence was immediately detectable — she hadn't done socially conscious stuff prior to “Love Makes the World Go Round,” and “Live to Tell” is a dramatically different ballad than the couple she'd done prior.

PL: I don’t think it was me that brought her into a place of social consciousness. [Laughs] I’m a guy who’s been staring at a piano and avoid social consciousness. [Laughs] I don’t think it’d be so good for me. I think I’d end up writing a lot of blues.

BC: What were your working sessions like when you were creating the True Blue songs?

PL: At the time, my studio was in my house, and I think she used to come to the house and we would work there from my demos. I had a Tascam 8-track and a lot of keyboard/synth gear. Usually, I would get up in the morning and go to work on something without any real idea of what it was gonna be, using whatever technology was available at that point — there weren’t computers yet, so there was just analog sequencers and synthesizers and drum machines, basically.

I would come up with something and I would show it to her, normally in two or three different sections. She’d give her input and we would make adjustments. Whatever things she heard, we would address and then she would sit and write the lyric and write a melody and then she’d sing it. The next day we’d do another song. I don’t remember any song that we spent two days on. I mean, when we went into production, we would work on them then, but during writing I remember it being a song a day.

I don’t remember a whole lot of “rejection notices.” I mean, we worked on almost everything. There’s a few things that I’m finding now that we never got to, but I’m not even sure that I even played them for her — maybe I knew they weren’t good enough. Pretty much, if something got started, it got finished, one way or another.

BC: Your Instagram followers were thrilled by the teaser you posted of the “Where's the Party” demo.

PL: On that tape, she sings a verse and a chorus and a verse and then she goes, “How’s that?” I know it was the first time she sang it, but when I hear it it reminds of how really great she is as a writer. In the final version, there were no notes different, no lyrics different, just a different performance. The woman is a bad-ass. [Laughs] The demos from Like a Prayer that I found — of course, people want me to post these things and I cannot do that and I hope everyone understands — in listening through these things, the lead vocal she did for “Like a Prayer” the day we wrote it is the lead vocal on the record, and it’s the same with a lot of those. That was it. “Cherish,” same thing — she sang it the day we wrote it, that’s the vocal. Again: bad-ass.

BC:: Your description of creating with Madonna sounds nothing like the process today, when every pop song has 20 writers and producers credited.

PL: In the days when I was working with Madonna, most of the times, these things would start at a piano with a piece of paper and a pencil. I’d actually sit at the piano and work out the chord changes, and then sit at the sequencer and work out a track myself. There wasn’t anybody doing anything to the demos, at that point, but me. The songs were constructed with the two of us in the room. If there were four people in the room, it would be difficult to argue that all four didn’t have a contribution. I think that’s what we’re seeing today with the multiple credits. It’s less isolated than the way we did it.

Click Here for All of Leonard's Work with Madonna!

BC: “La Isla Bonita” is one of Madonna's early-years songs to which she frequently returns — she sang it as recently as a couple of weeks ago in Saint-Tropez. Why do you think she's so fond of that one?

PL: The story about that one is, after the Victory Tour, I was still in touch with Michael [Jackson] and Quincy [Jones] and doing some work with them and Quincy called me and said, “I want to do something sort of Sade-like for Michael — would you write something?” and so I wrote that song and sent it to him with some form of a vocal on it and the phrase “la isla bonita.” He called up and said, “Ah, I just don’t think it’s for Michael.” Madonna and I were getting together, so I showed it to her and she said, “Oh, I like this, let’s work on it.” So we sat and changed, you know, whatever we changed and she changed lyrics and we reconstructed it. It’s a good song, for sure. I don’t know why she would return to that one more than others, to be honest. But I like it. It’s always easy — over the years, I learned to play “Live to Tell” and I can play “La Isla Bonita.” All the rest I have to re-learn them.

BC: “Live to Tell” was re-imagined with Madonna on a cross during her Confessions Tour. “Like a Prayer” is maybe the definitive Madonna song, and one she has performed in many different ways. How do you feel seeing such theatrical presentations of the songs you created?

PL: I grew up with prog rock bands who would dress up like neon triangles and say and do silly things and odd dramatic things — I think the right way is whatever way the artist wants to express it. As time went along, she certainly became far more expressive in the performances than when I worked with her. At that time, when I had little kids, I think I felt a little prudish about it — but I got over that. It’s that thing where sometimes people in the band don’t think lights are necessary because they’re playing so well, who needs lights, right? [Laughs] Thats bullshit, because you need it all and she certainly has done that brilliantly along the way. Truthfully, I saw the Super Bowl because someone sent it to me. Other than that, I haven’t seen much of these things ... There’s some part of me that doesn’t wanna see, I think. I care deeply about the work we did, but right now, what’s happening and how it’s reinvented and what it does ... I care that it means something to some people, but how it’s done, how it’s presented, just to sit and listen to it, this might seem weird, but I feel really detached from it.

My connection to it is musical; it’s not media-based at all. It's notes on the piano and words.

BC: Does the same apply when she changes the songs musically, not just the staging, during tours?

PL: Again, I’m not really familiar with the later versions.

Madonna with Leonard in the studio during the True Blue (L) and I'm Breathless (R) sessions.

BC: Did you always know which songs would become singles, and did you campaign for any?

PL: I don’t know that I had that much of an agenda there. But I will say that it wasn’t gonna be decided by anybody but her. So, the songs that were the best songs, the songs that we all loved the most, they were the ones. She knew. We knew. Having said that, “Live to Tell” wasn’t a popular idea with the record company when she wanted it to be the first single [from True Blue] with no edit on it, this six-minute thing that stopped and started three or four times — they weren’t happy. It was the same with “Like a Prayer” — they weren’t happy and they thought it was gonna be too complicated for people. I think she knew it and I think we believed in it together, in some way, but it wasn’t my place to decide. I would say if I thought something was a certain way, if I didn’t agree with her — but I don’t think it would’ve mattered. That’s not what I was there for. I wasn't there to decide how she was going to represent herself.

 The pieces that I liked the best, that I felt were somehow an accomplishment, that fulfilled something I was trying to fulfill — and really did get there — they’ve proven to hold up over time, but often they weren’t gonna be the first single, and I knew it then. I mean, I knew that “Oh Father” was not gonna be the first or second or third single, not when you have “Express Yourself,” “Cherish” and “Like a Prayer.” It’s gonna be a ways down the line. I was just grateful that it’s on a record that people are buying and you know they’re hearing it.

Why do you leave me wanting more?

Click here for the second installment of this interview.