Details About Madonna's Secret Fling With A Famous Rapper

Pop sensation Madonna has had quite the relationship history over the course of her decades-long career. She's been linked to the likes of Oscar-winning actor Sean Penn, eccentric basketball icon Dennis Rodman, and even "Ice Ice Baby" singer Vanilla Ice. But the Ice Man is hardly the only rapper Madonna has dated. In fact, she once had a secret two-year relationship with none other than late hip-hop legend Tupac Shakur.

Madonna and Shakur met in March 1993, and the two began seeing each other not long after. However, Madonna didn't publicly address the relationship until 2015, when she appeared on "The Howard Stern Show." During the interview, the "Like a Virgin" singer recalled her infamous 1994 appearance on "The Late Show with David Letterman," where she repeatedly dropped the f-bomb. Madonna attributed her attitude at the time to Shakur's influence. "I was feeling very gangster," she told Stern (via Entertainment Tonight).

Shakur's friend and fellow rapper Snoop Dogg himself went on "The Howard Stern Show" in 2018, and recalled the time he hosted "Saturday Night Live" in 1994. Snoop says he invited Shakur backstage, and was shocked when Madonna came with him. The D.O. Double G had kept the interaction a secret for nearly 25 years. As for why the secret romance didn't last, Shakur believed that being in an interracial relationship would hurt his image. He expressed as much in a 1995 breakup letter he wrote to Madonna while in prison. The letter surfaced online via TMZ in 2017.

The idea that Madonna and Tupac would cross paths isn't hard to imagine, but the details of how exactly they linked up make for quite the story all on their own. As it turns out, it was actually former "The View" co-host Rosie Perez who introduced the two. As she recalled during an appearance on "The Drew Barrymore Show" in 2024, Perez had been all set to attend the 1993 Soul Train Music Awards when her date unexpectedly canceled on her. "My date calls me up a half an hour before I'm getting in the car, and says, 'I can't go with you because my girlfriend will see me,'" Perez.

In turn, Shakur, with whom Perez was good friends, offered to be her date ... and maybe even help her get a bit of revenge in the process. "And he said, 'You know what, I'm gonna go with you, we're gonna walk up in there, we're gonna act like we're on a date, and he's going to die,'" Perez recalled. But once they got to the show, someone else ended up being quite taken with the "All Eyez on Me" rapper, and that someone was Madonna. "She was there and she came up to me and she was like, 'Yo, what's up? Y'all are together?' And I said, 'No,' she goes, 'Really?' I go, 'Yeah,' she goes, 'Hook me up. I said, 'You got it,'" Perez revealed.