Madonna Asked 'Dear Friend' Rosie Perez to Hook Her Up With Tupac Shakur

Madonna, Rosie Perez, Tupac Shakur.

Rosie Perez was the ultimate matchmaker for her “dear friend” Madonna and the late rapper Tupac Shakur.

Perez, 60, revealed during a Wednesday, November 6, appearance on The Drew Barrymore Show that Tupac was her last-minute date to the 1993 Soul Train Music Awards after her initial plus-one was a no-show to the ceremony.

“Madonna, she was there and she came up to me and was like, ‘Yo, what’s up? You guys are together?’” Perez recalled. “I said no, and she was like, ‘Really? Hook me up.’ I said, ‘You got it.’”

Madonna, now 66, dated Tupac between 1993 and 1994, but never publicly addressed the relationship until two decades later. (Tupac was killed following a 1996 drive-by shooting in Las Vegas at the age of 25.)

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“I was mad at [David Letterman] when I said the F-word a lot. I was in a weird mood that day,” Madonna said on the Howard Stern Show in 2015, referring to her expletive-laden appearance on The Late Show in 1994. “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.”

During the radio show, Madonna noted that she assumed that her relationship with Tupac was already public knowledge when she name-dropped the rapper.

Tupac ultimately dumped the Queen of Pop allegedly because of her race, according to a letter published by TMZ in 2017.

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“Can u understand that? For you to be seen with a black man wouldn’t in any way jeopardize your career. If anything it would make you seem that much more open [and] exciting,” Tupac reportedly wrote in the letter, dated January 15, 1995, amid his prison sentence. “But for me at least in my previous perception I felt due to my ‘image’ I would be letting down half of the people who made me what I thought I was. I never meant to hurt you.”

He added, “I offer my friendship once again this time [I’m] stronger [and] focused. If you are still interested I would like to further discuss this with you but some of it couldn’t wait. I felt compelled to tell you … just in case anything happened 2 me. Please be careful Madonna. Everyone is not as honorable as they seem there are those whose hearts bleed with envy & evil. They would not hesitate to do you harm! Let my 6 bullets be proof of that!”

Madonna subsequently filed for an emergency court order to block the impending sale of the letter via auction. A judge granted her request in July 2017.