Rosie Perez reveals she ‘hooked up’ Tupac and Madonna while they were on a date after he came to her rescue

Rosie Perez reveals she 'hooked up' Tupac and Madonna while they were on a date after he came to her rescue

As a lifestyle expert with decades of experience under my belt, I find myself constantly amazed by the intricate tapestry of connections that bind our world together. The story of Rosie Perez, Tupac Shakur, and Madonna is one such captivating tale that showcases the power of friendship, serendipity, and the unpredictability of life.


On The Drew Barrymore Show, Rosie Perez admitted that she played cupid and arranged a date between her good friend Tupac Shakur and Madonna.

Thirty years ago, the Pop Queen, now 66, and the tragically slain rap legend, who passed away at 25 in 1996, had a clandestine romance. Perez, aged 60 then, recently revealed that they first met when he accompanied her to the 7th Annual Soul Train Music Awards in 1993 as her date.

Perez shared that Shakur kindly suggested joining her at the event, as her original date cancelled just thirty minutes prior to their planned departure for the awards ceremony.

Barrymore inquired, “Were you and Tupac Shakur close friends way back when? Is that what I’m gathering from the story?

Later on, Perez reminisced about the time when her prospective date phoned her and shared: ‘I’m unable to join you as my partner might notice me.’

Rosie Perez reveals she 'hooked up' Tupac and Madonna while they were on a date after he came to her rescue

After expressing the truth to him and ending her initial date, she declared that her phone started ringing, and it was Shakur who said: ‘I’m coming with you. We’ll pretend to be on a date, and he will meet his end.’

Ultimately, Perez said she ran into Madonna, who asked if they were a couple.

After explaining they weren’t, she says the Material Girl hitmaker asked her to ‘hook’ them up. 

Perez, replied: ‘You got it!’ 

Shakur and Madonna are said to have had an on-again, off-again romance that spanned almost two years, ending in January 1995, with the relationship mostly kept private.

In 2017, a letter penned by Shakur in 1995, on January 15th, shed light on the reasons behind their breakup.

‘It wouldn’t harm your career if you were seen with a black man; it might even make you appear more progressive and intriguing. However, for me, based on my past beliefs, I felt that associating publicly with a black person could potentially disappoint half of the people who contributed to my success, according to my self-image.’ (ABC News)

He continued: ‘I never meant to hurt you.’ 

Rosie Perez reveals she 'hooked up' Tupac and Madonna while they were on a date after he came to her rescue
Rosie Perez reveals she 'hooked up' Tupac and Madonna while they were on a date after he came to her rescue

In another part of the three-page letter, Shakur penned: ‘A statement where you mentioned “I’m going to reform all the rappers and basketball players” or something similar… really struck a chord… I had never realized that you were associated with any rapper other than myself.’

He also apologized for not being the kind of friend that he’s ‘capable of being.’ 

He mentioned that his earlier stance should be seen in light of being a relatively inexperienced individual, especially considering the high profile and attractive nature of the person involved.

He ended by saying, “I’m not sure if you’d be interested in coming to see me, but if it’s possible for you, I’d really enjoy having a conversation with you in person.

Rosie Perez reveals she 'hooked up' Tupac and Madonna while they were on a date after he came to her rescue

According to Vogue, the letter was written during his stint at the Clinton Correctional Facility. 

Madonna was 34 and Tupac was 21 when they dated in the early 1990s. 

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2024-11-06 22:18

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