It wasn’t just your performances that were provocative. You didn’t write “Papa Don’t Preach,” but it’s impossible to imagine anyone else singing it. Why did that song speak to you?
It just fit right in with my own personal zeitgeist of standing up to male authorities, whether it’s the pope or the Catholic Church or my father and his conservative, patriarchal ways.
What was the fallout?
There have been so many fallouts, they all get confused. But for “Papa Don’t Preach,” there were so many opinions – that’s why I thought it was so great. Is she for “schma-smortion,” as they say in Knocked Up? Is she against abortion?
Any ideas you’ve had that you haven’t gone through with because they seemed too extreme?
I did a photo shoot with Steven Klein for my last album cover, and I painted my face black, except for red lips and white eyes. It was a play on words. Have you ever heard of the Black Madonna? It has layers of meaning, and for a minute, I thought it would be a fun title for my record. Then I thought, “Twenty-five percent of the world might get this, probably less. It’s not worth it.” It happens all the time, because my references are usually off the Richter scale. That’s why I have people like Guy [Oseary, her manager] in my life who look at me and go, “No, you are not doing that.”
A lot of fans consider “Live to Tell,” from your 1986 album “True Blue,” to be your defining song. What do you remember about writing it?
Sometimes when I’m writing songs, I’m just channeling. I could say that “Live to Tell” was about my childhood, my relationship with my parents, my father and my stepmother. But maybe not. It could be about something in an F. Scott Fitzgerald novel or a story that I heard once. It’s true, but it’s not necessarily autobiographical. I could say the same thing about “La Isla Bonita.” I don’t know where that came from.
Are you telling me you never dreamt of San Pedro?
I don’t know where San Pedro is. At that point, I wasn’t a person who went on holidays to beautiful islands. I may have been on the way to the studio and seen an exit ramp for San Pedro.
How did you come to write “Vogue”?
I wrote it when I was making Dick Tracy. After we shot the movie, [then-boyfriend] Warren Beatty asked me if I could write a song that would fit my character’s point of view, that she could have conjured up. She was obsessed with speakeasies and movie stars and things like that. The idea for the lyrics came through that request. Coincidentally, I was going to Sound Factory and checking out these dancers who were all doing this new style of dancing called vogueing. And Shep Pettibone, who co-produced “Vogue” with me, used to DJ there. That’s how it grew together.
What has been the biggest challenge of your career?
Working on Evita with Andrew Lloyd Webber and Tim Rice. It’s a whole different singing sensibility. I had to seriously work with a vocal coach to sing with strength and conviction. A lot of the stuff was recorded live, and I was in the recording studio with strange producers and writers, a huge orchestra and huge shoes to fill. The first song they wanted me to record was “Don’t Cry for Me Argentina,” which is the hardest song. I think I almost started crying. I felt very intimidated. Halfway through the recording sessions, I started to relax.
In 1998, you returned after a four-year break with “Ray of Light,” working with British electronica artist William Orbit. Why him?
After Evita I had a baby. Getting out of the world of pop music and pop culture for a while, I came back to it feeling very hungry, very curious, looking for something new. During that time I’d been listening to William Orbit’s Strange Cargo records. He’s very eccentric, he lives in his own world. I’d been away for so long that when I got into the studio with him, I felt like I’d been shot out of a cannon. I had so many ideas, and Ray of Light reflects that.
Most of your albums have been collaborations with under-the-radar producers like Orbit, Mirwais [2000’s `Music”] and Stuart Price [2005’s “Confessions on a Dance Floor”]. But for 2008’s “Hard Candy,” you turned to proven hitmakers like Timbaland, Justin Timberlake and Pharrell Williams. What was your thinking?
I always go, “OK, who’s making music that I like right now?” I really, genuinely like the music of Timbaland and Justin. Justin is a brilliant songwriter. I mean, “What Goes Around . . . Comes Around”? Brilliant. I thought it would be a challenge to work with him.