Madonna and Tupac’s Relationship: Examining the Prison Letter, Do ‘Homies’ Break Up

In the winter of 1994 thirty-six-year-old “sex symbol” superstar Madonna, allegedly pursued twenty-two-year-old Tupac Shakur first in New York and then again California. Shakur was gaining a reputation for being a ‘gangster’ and his many run-ins with law kept his name in the papers. The ‘like a virgin’ pop icon was reportedly worth over 100 million dollars, during the 90’s  she was on the top of her game.

Not much was known publicy about the nature of their relationship until recently. In a newly released ‘prison letter’ dated, January 15, 1995, an incarcerated Tupac writes what is clearly a reply to an early inquiry made by Madonna. He opens up with an explanation for his delayed response, “I’m struggling to find all the answers so that I wouldn’t leave any unanswered question,” Shakur writes.

Madonna’s letter is one among many correspondences that Shakur wrote. According to him his cell overflowed with letters from well-wishers, fans and supports all of which he tried to write back while locked up. Tony Danza and comedian Jim Carey were among his pen pals. During the time of his incarceration, Tupac is on record for dating Keisha Morris for one year and later married her on April 29, 1995, at Clinton Correctional Facility.

In the prison letter, Tupac addressed Madonna’s claims of him not “being a friend.” In response, he writes “I must apologize to you, because like you said I haven’t been the kind of friend I know I am capable of being.”

According to close sources, Madonna who is a seasoned industry veteran pursued this “young man with limited experience,” who was thirteen years her junior. In his interview with DJ Vlad Tupac’s stepbrother, Mopreme who traveled with and aided Tupac’s on the road says he was there in New York for the promotion of the Above the Rim movie a film released in March of 2014.

When prompted to speak about what type of relationship Tupac had with Madonna, Mopreme recounts the story in this way,

Interviewer: “What happened with him (Tupac) and Madonna

Mopreme: “Madonna is the homie.”

Mopreme: “We were doing press for Above the Rim”

Mopreme: “I think, we were in NY, Um.. just like them I was sitting there while Pac was doing the interview”

Mopreme: “Pac and Marlon they did it together, They were talking to Pac and Madonna came and sit down next to me and”

Madonna Says: “Umm ..when is he finished”

Mopreme: “ She gave me a note to give to him,,, I was happy she was giving him a note
I went over and gave it to him and ..”
Mopreme: “Then they linked up, I would take him to her house when we got back to LA, Yeh, they were a thing for a minute”

Mopreme: “She da homie.”

Interviewer: Were they in a real relationship?

Interviewer: Why did they have a falling out eventually?

Mopreme: “They were kicking it, you know what I mean. I don’t think it was super serious or they were gonna get married or some sh*t”

Another witness to the “hook up,” relays the story a bit different in this instance it is March 15, 1994, and a jilted Rosie Perez one of Tupac’s friend was reportedly distressed about being stood up for the Soul Train Music Awards that night. Tupac volunteered to take her as a last-minute replacement. The two arrived and the press mistook them for being involved.

In an interview in BRAVO hosted by Andy Cohen, Rosie recalls her sitting in the first row with her close friend Tupac and Madonna motioned for her to come over. Madonna supposedly asked to, “Hook her up.” In response, Rosie assures the infatuated Madonna saying, “ I got you, girl.” She goes on to say the next day you see Madonna walking around with the handkerchief Tupac ghetto style.

Funnily enough in an earlier interview, Rosie gave Wendy Williams a slightly different take on the, “hook up.” In that narrative Rosie claims, Tupac told her before arriving at the awards ceremony that one of the reasons he wanted to attend was because “he wants her to hook him up with Madonna.”

However muddled the timeline may seem Tupac never appears to deviate from his stance of Madonna being his friend, homie or as he said in this MTV interview that he gave upon his release from prison, “she was real cool like anyone of my homeboys.”

The two recorded the track, “I’d rather be your lover,” featuring Tupac, the version with him on it did not make it on her Bedtime Stories Album released in October of 94’. The song brandished a love struck Madonna whose desire for a deeper relationship unrequited by her love interest.

Headlines have spawned from the recent release of the Rikers Island response letter, many would have the public to believe Tupac dumped Madonna, “because she was white.” Oddly, the letter written twenty-two years ago tells a slightly different story. In it he expressed his concern about her intentions. He brings up the interview in which he claims she said, “I’m off to rehabilitate all of the rappers and basketball players,” he goes on to express that the words she spoke “cut him deep” and he didn’t’ know she was with any other rappers besides himself.”


The prince of, “keeping it real,” stated in a matter-a-fact way that Madonna being seen with a black man would not jeopardize her career but for him, it would have long reaching effects based on the ‘image’ he created for himself. Madonna is on record claiming she dated Tupac when asked about her erratic behavior on a 1994 David Letterman interview. She says they dated but he maintained they were homies/friends. This may be an issue of defining what classifies dating for “entertainment relationships.”

Much of the letter has been redacted, however, if we utilize the part that was revealed and couple it with the testimonies that have been left on record by several eye witnesses, one would be hard-pressed to conclude that Madonna and Tupac were anything more than “‘homies,” whatever that means.

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About Author
Emunah Y’srael is an expert in DIY Soul Improvement with over 20 years actively dedicated to her own soul journey. She is the creator of the a myriad of self-improvement projects. Emunah has authored to date four books, all available on amazon.

For question or comments on the contents of this article feel free to reach out:  @emunah_ysrael or

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