In a recent appearance on The Drew Barrymore Show, actress Rosie Perez dropped a juicy story from the 1993 Soul Train Music Awards that involved none other than the Queen of Pop, Madonna, and rap legend Tupac Shakur. Perez, who was promoting her new Apple TV+ series Before, revealed that she attended the awards show with Tupac after her original date canceled on her last-minute.
Perez recalled how Shakur stepped up, saying, “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.” At the event, Madonna approached Perez, asking, “Yo, what’s up? Y’all are together?” When Perez clarified that they were not, Madonna didn’t miss a beat, reportedly saying, “Hook me up.” And that’s exactly what Perez did, sparking a romance that later became legendary.
The link between Madonna and Shakur remained a rumor until 2015, when Madonna confirmed it on The Howard Stern Show. She shared that her relationship with Shakur gave her a new, fiery outlook that famously influenced her on-screen appearance with David Letterman.
Years later, a personal letter from Shakur to Madonna surfaced, detailing why the rapper chose to end their relationship. Though the letter's auction was initially halted due to Madonna’s legal action, it ultimately went up for sale in 2019.
