How Madonna Met Tupac: Rosie Perez Revisits Playing Matchmaker For Two Legends

On Wednesday’s (Nov. 7) episode of the Drew Barrymore Show, Rosie Perez once again recalled how she played Cupid for the Queen of Pop, Madonna, and the late, great Tupac Shakur.

The former In Living Color Fly Girl dancer and longtime friend of Pac spoke about the night of the 1993 Soul Train Music Awards, when she was stood up by her date and the “California Love” rapper stepped in.

“I was like, ‘You mother…!’” she remembered screaming into the phone. She then shared that her phone rang again, but it was Pac. After hearing her out, she said Pac didn’t hesitate to be her replacement. “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 him saying.

As Perez and Pac rolled to the award show together, she then shared how the night took a turn when Madonna asked her to introduce her to the rap star. “Hook me up,” she recalled the “Material Girl” icon saying, to which Perez asserted, “You got it.”

And the rest was history.

The two musical legends became one of the most talked-about secret relationships of the ’90s.

Madonna and Tupac’s romance flew under the radar from 1993 to 1994, with the 66-year-old confirming their fling in a 2015 Howard Stern interview. Snoop Dogg also told Stern in 2018 that he would see them together in the past—recalling a time Pac dropped off some weed to him while Madonna was with him.

“She was just riding along for the ride,” the West Coast legend said at the time.

Besides an electrifying romance, the couple also had a business relationship. The two reportedly recorded music for Madonna’s 1994 Bedtime Stories album, although the track never saw the light of day. She also shared that when Pac was sent to prison in 1995, he wrote her a heartfelt apology expressing regret from their breakup.

Sadly, he died a year later at 25.