‘Hook me up’: Tupac Shakur founded ultimate blueprint of temptation when he won over Madonna by dating Rosie Perez

There is a lot about rapper Tupac Shakur that is shrouded in mystery, particularly the still-formally-unsolved case of his murder. But the less murky details about his life have been hitting the spotlight now and then, with Rosie Perez reminiscing how the young singer managed to enamor Madonna (yep, THE Madonna) by going on a date with the Fearless star.

Something doesn’t add up, does it? Are you wondering whether the Queen of Pop was the villain in a budding love story? Hold your horses, will you, because this story has no villains, only one hero — Shakur. The backdrop? The Soul Train Music Awards in 1993.

As recounted by Perez on the Nov. 6, 2024 episode of the Drew Barrymore Show, her date stood her up at the last minute because he was worried his girlfriend would see him with her.

“So I was going to the Soul Train Music Awards and 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,’” she recalled, adding how the outrageous defense left her infuriated. After cursing out her lying and evidently, spineless beau, she hung up the phone, dejected and mad.

But proving to be a true friend with a strong bond with the former Fly Girl, Shakur happened to call at the exact time and after learning of what went down from a sobbing Perez, he instantly volunteered to be her wingman.

“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.'”

Little did he know that his one act of true friendship and kindness would unknowingly catch the eye of Madonna, who was also friends with Perez, and that she would instantly be totally invested in Shakur.

“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.'”

While the two kept it a secret at the time, Madonna did confirm the long-running rumor in 2015 that she and Shakur dated from 1993 to 1994 — a fact that the late rapper’s mother also confirmed — when she appeared on the Howard Stern Show. Evidently, before it all came to an end, Shakur got Madonna “all riled up on life in general” and “feeling very gangsta” when she was 34 and he was 21.

But as secretly as the relationship began, it reached a similar quiet end a year after it began. It wasn’t until Shakur’s letter to Madonna from prison — where he was serving time for sexual assault — dated Jan. 15, 1995, was leaked that the real reason of their breakup became known to the world. In his letter, Shakur apologized to Madonna, and highlighted how their separation was a result of his fear of how badly his career would be affected if it got out that he was in an interracial relationship.

Even though, Shakur and Madonna’s short-lived love story didn’t last, the rapper did what probably scores of men jostling for the “Die Another Day”s singer’s attention failed to achieve — impress the pop sensation. And Shakur did it unknowingly by just being a great, reliable friend.