On September 8 1994, Madonna presented the award for Video of the Year at the MTV VMA’s. She was escorted onstage by David Letterman, poking fun at their supposed feud following Madonna’s infamous profanity propelled appearance on Letterman earlier that year.
The appearance was intended to generate buzz for her soon-to-be-released single, Secret and its accompanying album, Bedtime Stories.
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 October 20 2005, Madonna was dared by David Letterman to get back on a horse – the first time since her fall (in August) which led to three cracked ribs, a broken collarbone and a broken hand. Madonna accepted the dare to ride again.
When asked why she hadn’t been on a horse since the fall, Madonna explained, “because my record company is not very keen on the idea of me injuring myself.”
On May 20 2015, Madonna acknowledged David Letterman’s retirement on Twitter:
@letterman Awww Dave I’m gonna miss you! Where am i gonna go on T.V. When I wanna say the F word? do you still have my panties???? this ❤#rebelheart loves you! – Madonna
On May 18 1994, Madonna made a surprise appearance on NBC-TV’s The Tonight Show, hosted by Jay Leno.
Watch this classic Madonna interview here:
On August 16 1985, Madonna and Sean Penn were married at a clifftop mansion in Malibu, California. Their wedding day was also Madonna’s 27th birthday.
Some of the celebrities attending the wedding included Rosanna Arquette, Tom Cruise, Andy Warhol, Cher, Martin Sheen, Rob Lowe, Carrie Fisher, Diane Keaton, David Letterman, Rosanna Arquette, Christopher Walken, Steve Rubell and many others.
Sean and Madonna later honeymooned at the Highlands Inn in Carmel, California.
Andy Warhol recalled this about the wedding:
It was just the most exciting weekend of my life. Martin went down to the hairdresser earlier in the day to have his hair done. We rode in a limo out to Malibu and when we saw helicopters in the distance we knew we were at the wedding. Somebody had tipped the reporters off about where the wedding was and about ten helicopters were hovering, it was like Apocalypse Now. And one helicopter had a girl hanging off with a camera and they were all trying to get in close. And the security people found camouflage-outfitted photographers in the bushes. And I looked really close at Madonna and she is beautiful. And she and Sean are just so in love. She wore white, and a black bowler hat, I don’t know what that was supposed to mean. And someone said that Sean had shot at the helicopters the night before. The only boring celebrity there was Diane Keaton, really. And it was the right mixture of nobodies and celebrities. Sean came over to say hello, and the good-looking family of Madonna was there, all the brothers. And you can see Madonna and Sean love each other so much. Really, it was the most exciiting thing ever.