Tupac’s Prison Letter Revealing Why He Ended Relationship with Madonna is up for Auction | The Urban Twist
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Tupac’s Prison Letter Revealing Why He Ended Relationship with Madonna is up for Auction

The letter addresses Tupac’s concerns about what the relationship was doing to each artist’s image.

Pascal Mnyika

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Tupac Madonna

Tupac Shakur, undeniably the greatest rapper of all time can be considered to be a prophet in his own context. Shakur’s lyrics and messages prophesied many occurrences that happened even after his death.


During his prison sentence, Tupac wrote about his relationship with Madonna, a pop icon, detailing of how he felt dating her would impact on their images. In his letter, Tupac stated that dating a white woman would lead to the tarnishing of his image at the expense of enhancing hers.

According to Vince Staples, the phrase “do it for the culture” is a deceitful construct that at times is used for some people selfish gains. To support his argument, Staples argued that most white entertainers remain relevant in the industry through the appropriation of the black culture.

Staples ideology is noticeable in the cordial 90’s letter, Tupac detailed on the reasons behind the brief relationship he had with Madonna. This indicates that the use of black culture by some white people to remain relevant started to form a while back and not a present-day issue as many people believe.

Tupac wrote “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. 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.”

Madonna in an interview with Howard Stern in 2015 spoke on how she revealed she was dating Tupac on during The Late Show with David Letterman. “I was mad at [David Letterman] when I said the f-word a lot. I was in a weird mood that day. 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.”

Tupac was irritated by this and he wrote in his letter, “[In] an interview where you said ‘I’m off to rehabilitate all the rappers and basketball players’ or something to that effect, those words cut me deep seeing how I had never known you to be with any rappers besides myself.”

However, Tupac amidst the noticeable frustrations while writing the letter apologizes for terminating their relationship snappishly and requests that Madonna visits him in prison.

Tupac’s letter is set to be auctioned for a starting bid of $100,000 at the Gotta Have Rock and Roll on the 19th -28th.

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