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Rosie Perez Recalls Madonna Asking Actress to 'Hook Her Up' With Tupac Shakur Before Singer's Secret Relationship With Late Rapper

Photo of Emilia Perez; picture of Tupac Shakur; image of Madonna.
Source: MEGA

Madonna asked Rosie O'Donnell for help sparking a romance with Tupac Shakur in 1993.

Nov. 7 2024, Updated 11:37 a.m. ET

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Rosie Perez was the match maker behind Madonna and Tupac Shakur's secret relationship in the 1990s.

During an appearance on the Wednesday, November 6, episode of The Drew Barrymore Show, the famed actress recalled introducing the Queen of Pop to the late rapper during the 1993 Soul Train Music Awards — three years before Shakur was fatally shot four times in the chest at age 25.

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rosie perez madonna asked hook up tupac shakur secret relationship
Source: MEGA

Rosie Perez took Tupac Shakur as her date to the 1993 Soul Train Music Awards.

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After Perez's original date to the awards show stood her up 30 minutes before they had planned to leave, Shakur stepped in to fill his place.

“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,'" The View alum, 60, remembered.

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rosie perez madonna asked hook up tupac shakur secret relationship
Source: MEGA

Pictured: Madonna in 1993.

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Once at the event, Shakur caught the eye of Madonna — who wanted to make sure he and Perez weren't an item before pursuing him.

"She was there and she came up to me and she was like, 'Yo, what’s up? Y’all are together?'" The Flight Attendant actress shared. "And I said, 'No.' She goes, 'Really?' I go, 'Yeah.'"

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rosie perez madonna asked hook up tupac shakur secret relationship
Source: MEGA

Tupac Shakur secretly dated Madonna from 1993 to 1994.

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After Perez's confirmation, Madonna asked the Oscar nominee to "hook [her] up," with the influential rapper, to which White Men Can't Jump star replied: "You got it."

Madonna and Shakur proceeded to be intertwined in a secret relationship from 1993-1994, however, the "Material Girl" singer didn't reveal their romance to the public until 2015 — almost 20 years after the "All Eyez on Me" hitmaker's murder.

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The "Like a Virgin" singer admitted she was "dating Tupac Shakur" in the '90s during a guest appearance on The Howard Stern Show nearly a decade ago.

"He got me all riled up on life in general," Madonna, 66, said Shakur, who she said made her feel "very gangster."

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rosie perez madonna asked hook up tupac shakur secret relationship
Source: MEGA

Pictured: Madonna in 1995.

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Tupac's brother, Mopreme Shakur, later confirmed the pair's relationship was real.

In 2018, Snoop Dogg also backed up the realness of Madonna and Tupac's romance, confessing to Howard Stern in 2018 that the pop star was once "along for the ride" with the late rapper as he drove over to deliver the "Drop It Like It's Hot" artist's weed.

One year later, a letter Tupac had sent to Madonna while he was serving time in New York for sexual assault was made public after it was auctioned off against her wishes.

Tupac provided reasoning behind his and Madonna's split in the message, writing: "At the risk of sounding over dramatic, the effects of racism make it difficult for a young Black man to properly show affection for an older white woman."

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