Madonna Dated Tupac Shakur & 5 Other Surprises From The Singer

Madonna's list of ex-boyfriends just grew by one – one icon of rap!

During her an interview with Howard Stern on his SiriusXM radio show on Wednesday, the Queen of Pop revealed that she briefly dated the late rapper.

While talking about her infamous "Late Night With David Letterman" appearance from 1994, where she dropped numerous F bombs, Madonna mentioned the relationship.

"I was mad at [David Letterman] when I said the F-word a lot," she told Howard about the 1994 talk show appearance. "I was in a weird mood that day. I was dating Tupac Shakur at the time and the thing is [Tupac] got me all riled up on life in general. So when I went on the show, I was feeling very gangsta."


Tupac Shakur in 1994 (Getty) Here are five more gems from Madonna's 90-minute chat with Howard Stern:

Was Told Her Career Was Over In 1984

"I just dove for [my shoe] on the ground, my dress went up and my butt was showing… and I didn't know my skirt was up. So, I proceeded to sing the song laying down on the ground. I was just making the best of a situation, which is what I do," Madonna said of her iconic performance of "Like A Virgin" at the 1984 MTV VMAs. "After I got off stage, my manager was white as a ghost. He looked at me and he said, 'Do you know what you just did?' I looked at him and I said, 'Yeah, I lost my shoe onstage.' And he was like, 'No, your butt was showing for the entire song.' And he looked at me and he said, 'Your career is over.'"

Considered Michael Jackson A Kindred Spirit

"I could certainly relate to him on many levels, but he was also a very shy person," she said. "He was famous since he was a child and didn't really have a childhood. He was painfully shy… We didn't really have a relationship about me revealing myself to him, but making fun of the crazy world we were living and working in. We didn't talk about our childhoods... I think he felt eternally tortured. It was hard for him to look into people's eyes."

Not A Jealous Girlfriend

"[Warren Beatty] was [an incredible lover]. I'm not going to lie," Madonna said of her ex, who dated Brigitte Bardot, Julie Christie and Elle Macpherson, adding, "I have confidence in my skills."

She Left Artist Jean-Michel Basquiat Due To His Drug Use

"We always think we can fix people and we can't...just change yourself," she said of dating the late artist in the '80s. "I loved him… When I broke up with him he made me give [his paintings he painted for me] all back to him, and then he painted over all of them black."

Why She Quit Doing Ecstasy

"I tried some ecstasy in the '80s, but I felt so ill for so many days after taking it. It wasn't worth it," she told Howard, adding, "I'm pretty fun when I'm drunk."