Stars You Didn't Know Madonna Dated

Madonna has a colorful—and extensive—dating history. The Queen of Pop has partook in a slew of high-profile romances, including her marriages to actor Sean Penn and filmmaker Guy Ritchie, her flings with baseball star Alex Rodriguez and Oscar-winner Warren Beatty, and her relationship with baby daddy and personal trainer Carlos Leon. But there are some stars who've hooked up with Madonna that blew our minds. Behold, the little-known past lovers of this musical legend.

Madonna's legendary foul-mouthed appearance on The Late Show with David Letterman in 1994 officially has a cause: her then-boyfriend, the late rapper Tupac Shakur. In March 2014, Madge told Howard Stern (via the Daily Mail), "I was mad at [Letterman] when I said the F-word a lot. I was in a weird mood that day. I was dating Tupac Shakur at the time and the thing is, he got me all riled up about life in general. He made me feel like a gangster." The tab also reported that the pair were introduced by a mutual pal, actress Rosie Perez.

In 2015, Shakur's brother told VladTV that Madonna and Shakur hit it off during the rapper's press tour for Above the Rim (1994). "She gave me a note to give to him," Shakur's brother, Morpeme, said. "[I didn't read it,] I was just happy she was giving him a note. Everybody was there, I went over and gave it to him. He was about the business and then they linked up. I would take him to her house and s**t when we got back to L.A. Yeah. They were a thing for a minute." He described the coupling as "off the chain" and "too much," adding, "They were kicking it. I don't think it was super serious, gonna get married or some s**t. You know how those entertainment relationships go. But they both respected each other, so it ended cool. He never talked s**t about her, not to me. And she never talked s**t about him."

What exactly went down between Madonna and comedian Sandra Bernhard is up for debate. The pair were close friends in 1988, even appearing on The Late Show with David Letterman together and twinning before twinning was even a thing. During the sit-down, Bernhard mentioned that she and Madonna slept together but later denied it. Whatever happened between these two apparently ended badly because more than 20 years later, Bernhard is still a bit bitter over Madonna allegedly abandoning her, telling talk show host Wendy Williams in 2011, "I'm cool with her, but we're not friends anymore, and it's really a bummer...I would have liked that to have gone on for a while...All is forgiven. You know, once you've gone to Kabbalah."

In December 2014, Madonna revealed she'd had an affair with artist Jean Michel Basquiat in the early 1980s. Though their relationship was brief, she says it impacted her forever. She told Interview magazine "Basquiat used to say to me, 'You're so lucky that you make music, because music comes out of radios everywhere.' He thought that what I did was more pop, more connected to pop culture than what he did," she said. "Little did he know that his art would become pop culture. But it's not like we really had discussions about the meaning of art. I remember hearing them talk about those things...I mean, Basquiat was my boyfriend for a while, and I remember getting up in the middle of the night and he wouldn't be in bed lying next to me; he'd be standing, painting, at four in the morning, this close to the canvas, in a trance. I was blown away by that, that he worked when he felt moved." She added, "He was constantly giving everything away. I think [he] felt guilty that [he] became successful...[he was] surrounded by people who were penniless, so [he] shared what [he] had...that rubbed off on me. You stay inspired that way." She added, "He was constantly giving everything away. I think [he] felt guilty that [he] became successful...[he was] surrounded by people who were penniless, so [he] shared what [he] had...that rubbed off on me. You stay inspired that way."

Unfortunately, Basquiat's drug use led to both his own demise and that of his romance with Madge. "He wouldn't stop doing heroin. He was an amazing man and deeply talented, I loved him," she told radio host Howard Stern (via Rolling Stone). "When I broke up with him he made me give [the paintings he gave me] back to him. And then he painted over them black."

Model Jenny Shimizu, who also had a relationship with actress Angelina Jolie, wrote in her book (via Pink News) that Madonna "used her as a sex slave" in the early 1990s. "I was her secret booty call available any time of the day or night for secret sex sessions," Shimizu alleged. Considering she provided no additional details, and Madonna has never mentioned this supposed escapade, we're willing to take this with a grain of salt—though the ladies were photographed together at least once.

Hip-hop one-hit wonder Vanilla Ice said he dated Madonna for eight months in 1992. "Going out with Madonna was exciting," he told News of the World (via Digital Spy). "She was older than me and a great lover. She's still the oldest person I've ever been with, so it was an experience."

Madge's infamous Sex book reportedly brought about their split. "I broke up with her after she printed [the book] because I was hurt to be an unwitting part of this slutty package," he said. "We were in a relationship, yet it looked like she was screwing all these other people. I thought she was taking pictures and running around naked because she was like that. Then when the book came out I was so embarrassed and ashamed. It was a porno...[she] threw me in like I was a product off a shelf, and I didn't appreciate it. That was it and I ended it," he said.