Madonna Dated Tupac Shakur; Is She Still Friends With Rosie O'Donnell?

She did! Madonna has confirmed that, yes, she did once date the late rapper Tupac Shakur. The “Living for Love” singer spoke about her former flame during an eye-opening interview with Howard Stern on Wednesday, Mar. 11.

The 56-year-old singer briefly mentioned her ex when Stern brought up her rant-filled 1994 appearance on The Late Show With David Letterman. At the time, Madge dropped the f-bomb 14 times, making it the most censored episode in American talk-show history.

“I was mad at [Letterman] when I said the F-word a lot. I was in a weird mood that day,” Madonna explained to Stern on his SiriusXM radio show Wednesday. “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 gangsta.” 

Tupac was shot and killed at 25 in Las Vegas in September 1996. Madonna added to Stern that she assumed her romance with Tupac was already public knowledge.

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Madonna — who spoke about her exes Warren Beatty and artist Jean-Michel Basquiat as well — also made another revelation: She’s still close with Rosie O’Donnell. The women starred as Mae and Doris, respectively, in the baseball fan favorite A League of Their Own in 1992. Back in 2009, O’Donnell told Stern that she studies Kabbalah like the singer.

“I adore her,” Madonna said, noting that the two first bonded because they lost their mothers at a young age. “That was our bonding for sure, but we have other things in common. She has adopted children and so do I. She’s funny and so am I.”

“We have a lot of the same likes and dislikes,” she added. “Doesn’t she make you laugh?” The women also make the time to visit each other at their homes.

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