Inside Tupac Shakur’s break-up letter to Madonna: “I must apologise”
Tupac Shakur had a reputation as a bit of a ladies’ man, and there is a long list of rumoured romantic relationships that he enjoyed during his lifetime. But one of his most A-list trysts was unquestionably the one he briefly shared with Madonna.
Their fling was kept under wraps from the public while it was taking place in the early 1990s, and it was only years later that it was ever confirmed. Madonna only publicly acknowledged that it had really happened in 2015, while she was appearing on The Howard Stern Show.
Her admission came amid a conversation about David Letterman, whose show Madge had appeared on in 1994. The interactions were supposedly quite frosty between her and Letterman, which, as Madonna explained, was actually down to her fling with Tupac.
“I was in a weird mood that day,” she told Stern. “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.”
Stern admitted to being surprised to learn that Madonna and Pac had dated, to which she replied, “I think people know, if you’re in the know.”
Unfortunately for Madonna, more details about her and Pac’s relationship would emerge in 2017, after TMZ managed to get hold of a letter that Pac had written to her from prison in 1994. The outlet published extracts of the note, which was about to go up for sale at auction.
Madonna had previously attempted to prevent that sale from happening, arguing that the fact that she is a celebrity “does not obviate my right to maintain my privacy, including with regard to highly personal items.” Her efforts failed, and the letter was sold in 2018.
Dated January 15, 1995, which was when Tupac was in jail on Rikers Island, the letter concerns the relationship between the rapper and Madonna, with Pac offering her an apology for how things had ended between them. “First and foremost,” he wrote, “I must apologize to you because, like you said, I haven’t been the kind of friend I know I am capable of being.”
Pac then explained that he had felt compelled to break up with her, largely because of the pressures associated with being a Black man dating a white woman. He specifically referenced an interview that Madonna had previously given, in which she had said something along the lines of, “I’m off to rehabilitate all the rappers and basketball players,” which Pac found distasteful.
“Can u understand that?” he asked Madonna in the letter. “For you to be seen with a black man wouldn’t in any way jeopardise your career. If anything it would make you seem that much more open & exciting. 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.”
Pac tried to close the letter on a positive note. “I don’t know how you feel about visiting me,” he said, “but if you could find it in your heart, I would love to speak face to face with you. It’s funny, but this experience has taught me to not take time 4 granted.”