So, Madonna dated Tupac in the '90s

Gallery: A history of Madonna's boos
We all remember Madonna dated Basquiat, and Sean Penn, and Dennis Rodman, and even a Kennedy, but somehow we forgot Tupac was in the mix too in the mid-'90s.

Madonna recently brought up their relationship in an interview with Howard Stern in relation to her infamous Letterman interview in 1994, in which she challenged Letterman for "kissing up" to guests, smoked a cigar throughout, and said "fuck" a lot. “I was dating Tupac Shakur at the time, and the thing is, he got me all riled up about life in general,” she said.

Tupac and Madonna dated for about a year before his death in 1996.

Meanwhile, that "yeherr" at the beginning is priceless.


Madonna also revealed she no longer does drugs after trying ecstasy in the '80s and feeling "so ill for so many days after taking it. It wasn't worth it." But she's "pretty fun" when she's drunk. She also commented on having sex with Warren Beatty, hanging out with Michael Jackson, and believing her career was over after performing 'Like A Virgin' for the first time.

"... 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. "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.'"

Little did he know it would foretell Madonna's career instead of ruin it.

Listen to the interview and watch the Letterman video below.


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