Madonna Opens Up About Dating Tupac, Felt ‘Gangsta’

On Wednesday radio jock Howard Stern interviewed Madonna on his SiriusXM show for a candid 83-minute conversation. One of the big news stories that came out of Madonna’s Howard Stern interview is that she dated the late rapper Tupac.

This has always been something that was speculated, but Madonna never really confirmed or denied the rumors that she had a brief romance with Tupac.

During the interview Madonna admitted that she was dating Tupac around the time she made an appearance on The Late Show With David Letterman in 1994. She explained the guest appearance on the show, and how at the time she was angry with Letterman.

“I was mad at [David 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 gangsta.”

So how did Madonna and Tupac actually meet? The two were reportedly introduced by actress, choreographer, and TV host Rosie Perez. During an interview on the Wendy Williams Show, Perez opened up about being the one responsible for the out of this world pairing. It all went down as the Soul Train Music Awards.

At the time Rosie explained to Wendy Williams that taking Tupac to the Soul Train Music Awards wasn’t her original plan. In fact, she was stood up by someone else in the music industry, and it was Tupac’s idea to go as her date instead. In exchange Tupac told Perez to hook him up with Madonna.

When Wendy Williams asked if he wound up leaving with Madonna, Perez simply nodded her head to confirm. “It was a crazy night because when we got out of the limo, I was so stoned and scared, and he’s like ‘Don’t worry, I got you.’ Then when we sat there I didn’t realize he was sleeping with half of the women in the industry.”

Tupac and Madonna dating wasn’t the only revelation that came out of the Howard Stern interview. Madonna revealed that she also felt very connected to the late Michael Jackson as well.

“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.”

[Photo by Gareth Cattermole/ Getty Images]