Madonna Reveals She Dated Tupac Shakur and Felt ‘Really Gangster’, Opens Up About Being Raped at 19

Madonna appeared on “The Howard Stern Show” Wednesday (Mar. 11, 2015) for the first time ever, where she opened up to Stern and Robin Quivers about dating Tupac Shakur before his tragic death, moving to New York when she was 18 and having a horrifying, violating experience, her success, her childhood, and much more.


The pop icon spoke candidly to Stern about being an entertainer and shock factor, such as when she adopted her children from Malawi (David and Mercy), or when she did songs like “Like a Virgin” or “Like a Prayer.”

Madonna, 56, then opened up about moving to the Big Apple from Michigan at a young age to be a dancer, explaining, “First I was in shock, I didn’t know a soul…I was saying hi to people on the streets like a dork.

Stern recalled a fascinating story he heard how she first arrived in New York with $35 in her pocket, wearing her winter coat in the middle of summer with no where to live yet, and some stranger (who she met at a flea market) asked what she was doing in a winter coat, and invited to her live on his couch. “The angels were protecting me,” Madonna added.

But her first year was tumultuous, from getting her possessions robbed multiple times, to her scariest moment during that early time. She explained it was her “stupid friendliness,” saying “I was going to a dance class and the door was locked and I needed money for the payphone. [A man] gave it to me…he was a very friendly guy…I trusted everybody.”

He convinced her to take the call at his place across the street, and said, “I was raped. The first year I lived in New York was crazy.”

Madonna explained to Stern why she didn’t file charges, saying, “You’ve already been violated. It’s just not worth it. It’s too much humiliation.”

As for why the young midwesterner didn’t go back home to Michigan after everything, she asked cheekily, “Well, have you ever been to Rochester, Michigan? I just didn’t want to go back. I can’t be around basic, provincial-thinking people.”

Madonna later confirmed a long-standing rumor that she and Tupac once dated in the early 1990’s. Stern asked her about the now infamous 1994 interview with David Letterman, and if she liked him (or was mad at him).

She replied to everyone’s surprise, “I don’t know, 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 about life in general. So when I went on the show I was feeling very gangster.”

Madonna also goes into detail about dating late artist Jean-Michel Basquiat, having her heart broken (and Rebel Heart, her latest album, which is all about heartbreak), working at and getting fired from Dunkin’ Donuts, being a fun drunk, and much more.

Listen to Madonna’s entire interview in the video above.

On the couch with Howard Stern. How did we end up here? (Rhetorical question) ❤️#rebelhearts

A photo posted by Madonna (@madonna) on