Do you still consider yourself a geek?
I say stuff like "oopsie-daisy." Growing up, I didn't feel cool, I didn't fit into any crowd. "Geek" is not a word anyone uses to describe me, though, except perhaps [Confessions on a Dance Floor producer] Stuart Price, who once said, "You know, you're a nerd at heart, nobody knows it." I took it as a compliment. I'm silly and geeky and nerdy and not cool.
You moved to New York after dropping out of the University of Michigan to become a dancer. How did you transition from dancing to singing?
It was just a question of circumstance. Because I was a dancer, I started going to auditions for musical theater, which forced me to sing. Most of the people auditioning were much more professional than I was — they brought sheet music, and they'd give it to the piano player, and I would just wing it and sing songs I knew from the radio, like an Aretha Franklin song or some other ridiculous embarrassment.
By 1979, you were living in Queens with Dan and Ed Gilroy, who had a band called the Breakfast Club, which you ended up joining. Around that time, you wrote your first song.
It was called "Tell the Truth." It was maybe four chords, but there were verses and a bridge and a chorus, and it was a religious experience. I had decided that if I was going to be a singer, I had to earn it. I had to learn how to play an instrument. We were living in an abandoned synagogue in Queens, and in return for music lessons I modeled for Dan, who was a painter. I was his muse, and he taught me how to play power chords. While they were off at their day jobs, I'd play drums. I learned by listening to Elvis Costello records. Then one day, I wrote a song, and the words just came out of me. I was like, "Who's writing this?" When their drummer quit, I got to be the drummer, and one night at CBGB I begged them to let me sing a song and play guitar. That microphone position was looking more and more inviting.
In 1982, you were signed to Sire Records on the strength of demos that included "Everybody," which went on to become your first single. When was the first time you heard yourself on the radio?
I was living on the Upper West Side, 99th and Riverside, and at about 7:00 at night I had the radio on in my bedroom, on [New York disco station] KTU, and I heard "Everybody." I said, "Oh, my God, that's me coming out of that box." It was an amazing feeling.
Did you call your dad?
I don't think I called my dad. I don't think he would have been very impressed.
How did you celebrate?
At that time I was hanging around with a lot of graffiti artists, Futura 2000, Keith Haring and Jean-Michel Basquiat. Jean-Michel introduced me to Andy Warhol. I remember we were all at a Japanese restaurant on Second Avenue and Seventh Street, where Keith had done a bunch of drawings on the walls, and Jean-Michel was telling me how jealous he was of me being on the radio. Because he thought that I had a more accessible form of art, and more people would be exposed to it. Andy told him to stop complaining.
Haring, who died in 1990 of AIDS, and Basquiat, who died of a drug overdose in 1988, were the defining artists of their generation. How did you meet them?
I was introduced to Keith by a roommate, but I had already seen his work on the streets, subways and buildings. Then we started hanging out at [legendary New York nightclubs] Danceteria and Mudd Club and the Roxy. The Rock Steady crew was there. We'd dance, we'd watch break – dancing crews there and on the street.
Did you do graffiti?
Walls, subways, sidewalks . . .
What was your tag?
No shit! Who came up with Boy Toy?
It could have been Futura. He's clever. He painted the whole inside of my bedroom on 99th, which my landlord was not happy about. We had a little gang — [actress] Debi Mazar was part of it. We called ourselves the Webo Girls — like hue-vos, girls with balls.
Do you own paintings by Warhol, Haring or Basquiat?
I have a few of each. Keith and Andy did four pieces for me as a wedding present when I married Sean. They're pictures of me from the cover of The New York Post when all the nude photographs of me came out in Playboy and Penthouse. The headline says I'M NOT ASHAMED. So they took all these Post covers and painted over them. They're in my house in L.A. — a signpost, a watershed moment. I also have a leather jacket that Keith Haring painted on that I would never give up.
Since the beginning of your career, the transformation of your image has been the only constant. Between your first two albums, 1983's Madonna and 1984's Like a Virgin, you went through your first major reinvention, from a punky brunette club girl into a blonde in a wedding dress. Where did that come from?
I don't know. I guess the music I started to write had more of a seductive quality, and I unconsciously morphed into that. It also had to do with the fact that I was doing more photo shoots. I was being styled and dressed. Before that, I was doing everything myself. I had no makeup artist, I was taking my dance tights and tying them around my head and throwing a few rosaries around my neck. After that, it was [photographer] Steven Meisel, and fashion people putting me in corsets. I think people put a lot of emphasis on the whole reinvention of my image, and it's always been a lot less calculated than people think. It's just evolution and what I'm interested in, the books I read or movies or clothes that I see. Just call me Zelig. Wasn't that the Woody Allen movie where he took on the personality of whoever he's talking to? I think it's boring to stay the same. A girl likes to change her look.
When you were inducted into the Rock & Roll Hall of Fame, there was a video montage of your career. When you took the stage, you made a joke about "all my bad hairstyles." Which Madonna fashion era do you look back on with the most disdain?
I think it was the purple-lipstick/fluorescent-green-sweater combo. So many of those hairstyles. It's OK, it was the Eighties. It was a bad-hairstyle era, let's face it.
On the flip side, is there a time you look back on when you say, "Fuck, I was pretty hot."
Like I'm going to admit to that! And be annihilated for the next 10 years for it? I'm not answering that one.
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