Oh, Madonna — who hasn’t she dated? I’m pretty sure Madge and I hooked up some time in the early-00s, but for some reason she didn’t bring that up on her first sit-down with Howard Stern. She did, however, casually mention that time she dated rap legend Tupac Shakur, who — turns out — was the impetus for her controversial 1994 Late Show with David Letterman appearance
“I was mad at [David Letterman] when I said the F-word a lot,” Madge told Stern. “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.”
Stern was surprised at the Tupac connection, though Madonna thought it was public knowledge at this point. According to E!, fly girl extraordinaire Rosie Perez told Wendy Williams she helped introduce the two. Way to be a national treasure, RoPez.
Among other revelations from Madonna’s first-ever Howard Stern interview, we learn that she dropped her shoe during her iconic VMA performance of “Like a Virgin,” leading her to writhe all over the stage to retrieve it. Her manager at the time correctly predicted that her career was over.
And while she doesn’t do drugs anymore, Madonna’s a self-described fun drunk. Here’s an example:
Les Fabian Brathwaite, openly questioning the identity of Lola’s father now.