In 2015, Madonna casually revealed during an interview with Howard Stern that she once dated Tupac Shakur. Madge was talking about her infamous 1994 Letterman appearance, during which she called the host a “sick fuck” for being so obsessed with her sex life. “I was in a weird mood that day,” she said over 20 years later. “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.”
Rumors about the two had been floating around for a while, but their relationship might have been deeper than anyone thought – according to a newly-surfaced letter that Tupac wrote to Madonna from prison. The letter is dated January 15, 1995, one year and eight months before the rapper’s death. It’s a little over two pages of Tupac apologizing to Madonna for breaking up with her because of the implications of him dating a white woman.
“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 writes. “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.” TMZ reports that the letter will go up for auction between July 19-28 at auction site Gotta Have Rock and Roll.
Tupac says he was hurt by an interview in which Madonna suggested she dated other rappers, which prompted him to strike back and defend his ego. “I offer my friendship once again this time my stronger & 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,” he wrote, before ending with a heartfelt warning. “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!” Tupac wrote. “Let my 6 bullets be proof of that!”
This isn’t the only one of Tupac’s high-profile relationships to make headlines recently. Jada Pinkett-Smith, who he dated when the two were teenagers at the Baltimore School of Arts, is being “reimagined” in the controversial new Tupac biopic All Eyez on Me. In response to Jada calling out the factual inaccuracies in the film, fans resurfaced a love poem that Tupac wrote to his then-girlfriend. Clearly the rapper’s way with words went far beyond music.
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Text Hannah Ongley
Photography Patrick McMullan via Getty Images