Yesterday, I published the first part of my chat with Patrick Leonard, the musician who co-wrote so many classic songs with Madonna, and who is bringing an instrumental show of their work to NYC on September 12 at Joe's Pub.

Click Here for Part 1!

Now, check out the second and final part of the interview, in which Leonard talks about how his daughter inspired “Dear Jessie,” the time he lost seven Madonna tracks in a limo and his work with Ms. Ciccone on the aborted film project Hello, Suckers! ...

Leonard's Who's That Girl World Tour jacket, freshly out of storage (Image by Patrick Leonard)

BC: “Who's That Girl” is one of those songs whose title is used over and over to describe Madonna. Was there any thought put into its application to her overall mystique, or is that way reading into it? [Laughs]

PL: Way overthinking it. [Laughs] We were working, and there was a movie, and she needed songs for it, and we wrote them. And the movie was called Who's That Girl. [Laughs] Or did they change the name of the movie after we wrote the song? [The film was originally entitled Slammer. — Ed.]

BC: So many of Madonna's movie songs are superior songs. What was it about doing what was essentially an assignment that led to such amazing records?

PL: This is heady, philosophical bullshit, but when you have a 90-minute piece of content and a bunch of people involved with different desires and needs and agendas and storylines, there’s just a lot of emotional energy that you can put your toe in. Suddenly, there’s this giant, moving thing around you that took people years to make. I believe you can tap into that. It’s a lot harder staring at a blank piece of paper alone.

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

BC: Madonna is often characterized as manipulative and very planned out. When you were working on Like a Prayer, did she come to you with any direction as far as this being a more personal record, a real reinvention?

PL: I think it happens naturally. In hindsight, I can see it. I remember the conversations we had, even questions about lyrics. She’d ask, “Is this too direct?” I remember these things happening innocently. If there was a grand plan, I didn’t know what it was.

BC: I've always thought she was just better at working with what happened to her rather than knowing how everything she did would be received.

PL: That’s what an artist’s job is — to reflect what’s going on; in some ways, to reflect and enhance and embellish.

Madonna with the famous Jessie (Image by Patrick Leonard)

BC: I must ask you about “Dear Jessie” since it was named for your daughter!

PL: I have a moment in my mind that I remember, because in my studio, Madonna would sit on the couch and I would sit at my keyboard and I would show her what I had and we would make adjustments and we started working on that song and it just didn’t quite make any sense at first — it was a subject matter question. I remember using the song and title “Dear Prudence” as a reference and she said, “What about ‘Dear Jessie’?” and I said, “That’ll work.” She then wrote those lyrics and sang that demo. Bad-ass. And I have that demo, too, the day we did it. I put a little snippet on Instagram and people were saying, “God, it changed so much.” Truth is, we took the drums off. Otherwise, it’s the same recording. [Laughs] We added a couple other little things to it.

Madonna with Jessie at the icon's 29th b'day party in London (Image by Patrick Leonard)

BC: When did your daughter realize how cool it was to be the basis of a song composed by her father and Madonna?

PL: I think she was in her twenties. People started saying, “You’re the Jessie from ‘Dear Jessie.’” She thinks it’s cool. There’s quite a few pictures of them together. Madonna’s an incredible mother and loving parent and in those days, here was this adorable little girl that was around all the time and they bonded, they really did. For that laugh on “Dear Jessie,” Jessie came down to the studio on the last day and I think my assistant chased her around the room to make her laugh. It was her first overdub. [Laughs]

BC: I wanted to ask you about non-Madonna album tracks, like “Just a Dream” for Donna De Lory, “Possessive Love” for Marilyn Martin and “Tell Me” for Nick Kamen. You worked on these with Madonna, but were they intended for her and then handed off?

PL: I think “Possessive Love” was just me asking her a favor. And the Nick Kamen song, I remember she knew Nick and Nick’s brother Chester had played guitar on Like a Prayer, so it was just something like, “Keep it in the family.” I don’t think any of those songs were songs we wrote and didn’t use and somebody else got them. There’s only a couple of songs, and there might not even be a couple — “Angels with Dirty Faces” is the only song I can think of where we wrote a song and wrote a lyric and made a demo and didn’t use it.

BC: People freaked out over “Angels with Dirty Faces,” an unused track from the Like a Prayer sessions. Can you tell us a bit more about that?

PL: I was surprised to find that one. When I heard it, I thought, “Oh, yeah, I forgot about this.” It all came back to me, and as it was playing, I thought, “This doesn’t quite work.” [Laughs] If you heard it, there’s all of these good things about it and it sounds great and she sounds great singing it and it seems like a must, but there’s that weird, intangible thing where you go, “There’s something missing. This one isn't gonna work.” I have an issue with record companies that release albums from people that were made years ago and they put these bonus tracks on it of stuff that didn’t make it on the original release. Most likely, the artists didn’t want you to hear this in the first place; they probably still don’t.

BC: Did the '30s Tin Pan Alley sound come easily for you when you did the I'm Breathless tracks with Madonna?

PL: It was easy-ish because my dad was a jazz sax player, influenced by that era. So I grew up with Gershwin and swing and big bands. I played “standards’ with my dad when I was 10 years old. So that style is somewhere tucked away in me.

I was just looking at the original chart for “Something to Remember,” and there’s not even an eraser mark on the page. Almost like I knew what I was doing. [Laughs] We did the whole thing, start to finish, in about three weeks. I remember that it was fast and fun to do.

BC: After that, it was a while before you did “I'll Remember.” Madonna is often attacked as a love 'em and leave 'em artist; did you ever think you had just worked with her for the last time? Was that a concern?

PL: No. We weren’t a band. These were choices. “I’ll Remember” came with With Honors. I did the score for With Honors, which was directed by Alek Keshishian, who was a very good friend of hers. Richard Page [of Mr. Mister] and I actually wrote the initial version of “I’ll Remember” and I don’t remember, I think Alek asked her if she would come in and sing it. She came in, she made some changes in it, I don’t remember how much she changed, but I know that Richard is credited on it and I know that he and I worked on the song initially. I found a cassette with just piano and her singing it the first time and her saying, “Okay, let’s try it.” Like always, she nails things. I don’t know exactly where the lyric content came from. I don’t know if Richard wrote ‘em or Richard wrote ‘em and she changed ‘em — I don’t know. “I’ll Remember” is not about my memory. [Laughs]

BC: After all the '80s pop, the rock of Like a Prayer, the '30s ditties — how at ease were you with Ray of Light, another right turn for Madonna on which you worked?

PL: We went to Florida to write those songs. She and I were in touch, and we hadn’t been in touch for a long time. I recently found the letters that went between us before we started work, where we decided to do this again. These letters say a lot about the decision process. It’s, “Oh, yeah, we wrote some really good songs together, let’s do it again.” [Laughs]

She did give me some direction early on. For “Frozen,” she said, “I would like something that’s The English Patient meets Nine Inch Nails.” We’d done the demos in Florida, which were quite different than what the record ended up because of William Orbit — who did genius work — but it was exotic, maybe not electronic necessarily, but maybe more exotic ... we had chant samples and were really planning on going for it in some crazy way, and then William came along and she wrote me and then we spoke and she was very generous about saying, “Is it okay if I do this, because I think he’s brilliant and I think it’s a good idea.” In the way these things go, all I could do was be supportive and as it turns out, I’m very glad I was.

But the demos for that record are fun, like for “Skin” and “Sky Fits Heaven” — they’re so bizarre! And I’ve never even heard of anyone having them.

I had a terrifying experience. When we were leaving Miami, having written them, I had a cassette that just said “M” on it and I had a rental car and when I returned the car, I left the tape in it. When I got on the plane, I thought, “Oh, my God ... I just left seven new Madonna songs on a cassette in a rental car ...” but they never turned up. So someone took that cassette outta there and they threw it away. [Laughs]

Leonard speaking about Madonna's musicality in 2001 on Swedish TV

BC: Every true-blue Madonna fan knows about Hello, Suckers!, the proposed movie musical about Texas Guinan you worked on with her in 2004 but that was ultimately abandoned. What do you remember of those sessions?

PL: It was a re-imagining of cabaret stuff, and I don’t remember how many songs we did — I’m currently transferring those drives just for safety’s sake because they’re on an old format — but they were reimagined things and I think we wrote two new songs. I don’t remember the names of them. One of them was a ballad. And I remember that we sat and wrote this song, I think I’d done the musical part in the morning and she showed up and wrote the lyric and went in this little booth in this little studio I had at the time and sang it and came out and said ... what did she say? “Just like the old days” or “Some things never change,” something along the lines of, “Sounds like another great song.”

These were funky, funky demos. These weren’t the kind of demos we were doing in the early days where I was doing them in my studio with all my stuff hooked up and knowing that potentially everything we recorded was gonna turn into a record, so, “It should be as good as we can get it right now.” This was kinda funky, like, “Let’s just get these demos done.”

It got caught up in some kind of political thing and it just went away. I thought it was cool at the time. I thought it was a good thing, and there were some things on there that were really fun. I’m remembering that she was ferocious like she always was, doing these performances that were really off-the-wall, but really brilliant.

“Boum,” which leaked a few years back, and was not supplied by Leonard. 

BC: Madonna once said Patrick Leonard “encouraged her as a songwriter to dig deep and explore areas of my emotional life that I possibly hadn't really gotten into yet.” You gave her that ... what do you think she gave you?

PL: She’s so much stronger than me; if I taught her anything, it was how to be weak.

BC: You taught her well! She has many beautiful moments of vulnerability in her work, most of which are overlooked in favor of the tough stuff.

PL: That’s for sure. What did she do for me? It’s a big question. There’s a lot that she did for me. In all these years in all this stuff, there was a flicker of unintended disrespect on my part. We got over it. There’s always been mutual respect, and I think that it isn’t often where the artist and the unseen collaborator feel like they shared equally and fairly, and I do.

Something about humility and gratitude, really. When I’m on Instagram and people say, “You guys need to work together,” and, “She needs you,” I wish there was a way I could get them all in front of me and say, “You guys, this isn’t right and this isn’t fair to her. You’re still fans and you need to really look at what she’s doing and what she’s trying to say. It may well be that there’s a subtlety in it that’s everything you need, you’re just not looking ‘cause you’re stuck in the past.” It’s not fair to her and I don’t like that, nor would I want someone saying it about me. It’s one of the reasons I’ve avoided looking back on music. I don’t want to go back to something and have people say, “That’s the best thing you’ve done.” I was 28 years old then, I’m 61 now. So what should I do? Bury myself in the yard? [Laughs]

It’s difficult for artists. There are almost none that I know that’ve actually been able to somehow do it more than a couple times. At some point, it’s sort of your job to teach, and you teach with what you’ve created because it’s your reference book, it’s the textbook you made, and it’s just the way that we’re wired. As much as I’m still trying all the time, it has occurred to me that it’s time to look back and talk about these things a little bit because they have value to people ... and maybe there’s some lesson or some story or something in them.

BC: Madonna is consistently attacked as a non-artist, someone who has somehow skated by for 35 years on sex and hype. How do you react when people scoff at her musicality, who don't see her as an artist?

PL: It pisses me off, to be honest. The people that do get credited as being real artists oftentimes are just “cool” and that gets interpreted as art. And these days, there are way too many talent-show winners, and they get called artists because they have some crazy-good voice. I have issues with these things, but I won’t go into it because I’ll probably have my house burned down by the people that make Auto-Tune. I can assure the world listening and looking at Madonna that they don’t have any reason to ever defend her or feel insecure about it and all I can say is I’ve worked with a lot of people — I’ve worked with a lot of people — and ... hard to be any better or more artistic than her.

There’s people with a more controlled voice — the word “better” is not fair, because how can you have a better voice than the voice that sang “Like a Prayer”? You just go through the list of singer-songwriters through the years — Neil Young, Bob Dylan, Leonard Cohen, none of these people were “singers” But these are the ones that the most art came from. I think her lyrics were taken for granted all those years ago; you look at the individual lines and this is what people need to think about now, those statements she made all those years ago. I’m certain she’s still doing it.

My knee-jerk is to defend her always, but when I have the demos where she sang a song, having written it 15 minutes before, and it was a #1 record and remains valid 30 years later, who’s gonna tell me that’s not a real artist?