On March 11 2015, Madonna was interviewed by Howard Stern on SiriusXM.
Here are some tidbits we learned about Madonna during the interview, according to Rolling Stone magazine:
- Her shocking VMA debut of “Like a Virgin” was an accident. “I had come down the wedding cake and my shoe fell off,” she said. “I was like ‘Oh shit, I can’t dance in one shoe!” The mishap prompted quick decision-making on Madonna’s end as to how to proceed with the performance and led to the controversial stage-humping that took place at the first Video Music Awards. “I didn’t know my skirt was up. I proceeded to sing the song laying down on the ground. I was just making the best of the situation.” She noted that her manager Freddy DeMann told her that her career would be over following the performance.
- She craves normalcy every once in a while. “Every 3 days I crave it,” she said. “Every three days I go, ‘That’s it. I’m moving to a cabin and living in the forest and no one’s gonna fuck with me anymore.'” Stern probed as to why she thinks she could never give up her career and life in the spotlight. “Because I’m an artist and I’m tortured. I’m a masochist and I like to create. I don’t know. Maybe one day I will.”
- Madonna’s first year in New York included multiple robberies, an assault and an unreported rape. “I needed money for the payphone and [a stranger] gave it to me,” she said. “He was a very friendly guy, and the phone was ringing. He was like, ‘Oh, I live right across the street if you’d like to make the phone call from my house.” The then 19-year-old Madonna agreed, blaming her “stupid friendliness” from her Midwestern roots. “I trusted everybody. The rest is not worth talking about.”
- She doesn’t hate David Letterman. Stern acknowledged some early interviews between the pop star and talk show host, noting he could never tell if she liked him or was annoyed. “Oh, that’s how I flirt with people,” she revealed. “One time I was mad at him, when I said the ‘f-word’ a lot, but the rest of the time was good.”
- She dated Tupac Shakur. The late rapper had actually been the reason Madonna was mad at Letterman. “I was dating Tupac Shakur at the time, and he had gotten me all riled up about life in general,” she said. “When I went on this show, I was feeling very gangster.” Stern revealed his surprise about the little-known past relationship. “I think people know, if you’re in the know,” said Madonna coyly.
- The misunderstood meaning of “Material Girl” gets on her nerves. “The song that irritated me the most about being associated with me is ‘Material Girl,'” she said. “It was an ironic song because I’m certainly not a materialistic person.” The topic came up as Stern had her clear up a rumor that she detested the success of “Like a Virgin” because other people had written it. The singer declared the rumor false, asserting that she loves the song and appreciates its writers.
- Upon making her first $1 million, she indulged in buying a Frida Kahlo painting. “That was always my goal,” she said on her art collection. “When I was married to Sean [Penn], I said ‘When I make my first million, I’m going to buy art.'” Madonna had been a huge fan of Frida Kahlo since she was young. “I bought a self-portrait of hers. At the time it was rather inexpensive because people didn’t know who she was.”
- Jean-Michel Basquiat destroyed all the paintings he had given to her. Madonna and Basquiat had dated when the singer was very young, but his heroin addiction ended up pulling them apart. “He was an amazing man and deeply talented. I loved him,” she said. “When I broke up with him, he made me give all [his paintings] back to him. And then he painted over them black.” She regrets giving the art back, but felt pressured to do so since it was something he had created.
- She wrote “Vogue” in a few hours. Madonna stands by the idea that her best songs are the ones she wrote in only a couple of hours, “Vogue” included. “I thought it was a very cool dance, very presentational and elegant and all about vanity,” she said about the dance of the same name. The song had been written for Dick Tracy, the film she made with ex-boyfriend Warren Beatty, and was inspired by all the classic movie stars. “[Warren] dated all of Hollywood, basically.” She would ask him questions about what the stars she admired — and he dated — were like, including Natalie Wood and Julie Christie. “I looked up to [these women] and admired them.”
On December 19 1990, the film Dick Tracy was released on home video.
Here’s a video I put together for one of our favorite songs from the film, Stephen Sondheim’s More.
On March 20 1990, the lead single from Madonna’s I’m Breathless album, Vogue, was released.
Vogue was written and produced by Madonna and Shep Pettibone in December 1989. The song was recorded with the intention of being the b-side to the upcoming (and last single for the Like A Prayer album), Keep It Together (released on January 30 1990).
The finished product was too good to be a single b-side, so it was decided that Vogue would be a stand-alone single on Madonna’s forthcoming album, I’m Breathless (even though the song had nothing to do with Dick Tracy).
On December 4 2011, shoe designer John Fluevog told the Calgary Herald’s Theresa Tayler that he never expected that Madonna would pay her respects by whipping out a pair of shoes he had gifted to her, putting them on during a scene in her infamous, documentary Truth Or Dare.
“Yah like ‘em?!” she said, as she flirted with the camera, showing off the “Munster” platforms. At the time, it was a massive publicity break for the respected, but still little-known, Canadian designer.
Fluevog told Tayler that he rarely tells the story of how Madge ended up with a pair of his kicks:
“I don’t really like giving away shoes. It’s not what I do. This is a business. One night I was watching Madonna on one of those American talk shows. She was being very naughty, talking about spankings and saying all of these silly things. I thought, this is a game player. Her whole thing is a game. She needs a pair of my shoes.”
Fluevog then sent one of Madonna’s stylists a pair of his shoes and he never heard back.
“Not a thank you, not anything. Then, someone told me she wore them in the movie . . . I didn’t like Madonna’s game. I found it annoying, but I respected what she was doing. The movie moment was a game-changer for Fluevog. Things exploded for us. It was all a bit of shock to me.”
On July 2 1990, Madonna was featured on the cover of People Magazine with Warren Beatty to promote Dick Tracy.
“Tell me you want me,” Breathless Mahoney implores to Dick Tracy in the wide-screen moonlight. “Tell me you want it all.”
On June 22 1990, the second and final single from Madonna’s I’m Breathless album, Hanky Panky, was released in North America.
Greg Sandow, from Entertainment Weekly, called the song a “delightful challenge to censorship”.