Madonna revealed that she one dated rapper Tupac Shakur in a recent in-depth interview with Howard Stern.

Madonna Dated Tupac Shakur

Stern interviewed Madonna on his SiriusXM radio show Wednesday, and the singer was shockingly honest throughout the 80-minute interview. When speaking about her 1994 appearance on The Late Show With David Letterman, in which she swore at the late night host, Madonna revealed that she was dating Shakur at the time of the interview. In 1994, Madonna appeared on The Late Show With David Letterman and confronted Letterman about how often he makes jokes at her expense on his show. “Don’t f—k with me, Dave,” Madonna told Letterman at the time. Looking back, the singer explained that she was in a particularly rebellious mood that day, something she credited to her then-boyfriend.

“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 on life in general. So when I went on the show I was feeling very gangster,” Madonna told Stern.

When Stern expressed his surprise at the news of a romance between the singer and the infamous rapper, Madonna said she thought their relationship was already public knowledge. “I think people know, if you’re in the know,” Madonna teased.

Madonna Explains Why She Didn’t Press Charges After Her Rape

Madonna also commented on another ex, Warren Beatty, admitting that she was completely in love with the actor. The singer also touched on her rumored drug usage – she says she no longer does any drugs other than drink alcohol – and her experience being raped as a young woman in New York.

Madonna recounted how she was attacked by a man she met on the street, and told Stern that she did go to the police initially, but decided not to press charges because she felt humiliated by the entire process. “You’ve already been violated… It’s just not worth it. It’s too much humiliation,” Madonna said.

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Article by Olivia Truffaut-Wong

Olivia Truffaut-Wong was born and raised in Berkeley, California, where she developed her love of all things entertainment. After moving to New York City to earn her degree in Film Studies, she stayed on the East Coast to follow her passion and become an entertainment writer. She lives on a diet of television, movies and food.