Tupac Shakur’s Break-Up Letter to Madonna

Tupac Shakur and Madonna dated briefly in 1994. According to Tupac’s brother Mopreme, the relationship began when Madonna passed Tupac a note during a press day for Above the Rim. The two of them broke up sometime before Tupac was shot on November 30, 1994 as part of a robbery at the Quad Recording Studios in Manhattan. Shortly after he was shot, Tupac was convicted of three counts of molestation as part of a sexual abuse case brought against him in 1993.

While in jail, Tupac wrote a letter to Madonna. This letter appears to have been sold at auction by Madonna’s former friend, art dealer Darlene Lutz, in 2018, after Madonna lost a legal fight to have it returned to her and keep it from being sold. Exactly what became of the letter is unknown.

It’s a remarkable letter, although parts of it have been blurred out by the auction house. The Independent focuses on the fact that Tupac was concerned about being seen publicly dating a white woman:

Can u understand that? 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.

Tupac was also upset by an interview that Madonna gave where she said, “I’m off to rehabilitate all the rappers and basketball players.”

“Those words cut me deep seeing how I had never known you to be with any rappers besides myself,” Tupac writes in the letter. “It was at this moment out of hurt & a natural instinct to strike back and defend my heart & ego that I said a lot of things.”

In her note on the letter, “Please Do Say Forgive Me,” Chandra Steele focuses instead on the nature and quality of Tupac’s apology.

Celebrities are separated from us by our perception of their godlike attainment of what we’re supposed to want: fame and money and sex. But when Tupac refers to their relationship, he uses words of humanity and humility. “I haven’t been the kind of friend I know I am capable of being” is how he frames the apology. It’s an empathy that some never access within themselves, no matter how many classes they take in unlocking their chakras. Later he tells Madonna, “I offer my friendship once again, this time much stronger and focused.” …

What’s more remarkable than what’s written is what isn’t. Tupac does not overstep the bounds of being an ex-lover. He does not push a selfish agenda. He has the wisdom to balance what he wants with what is warranted after leaving sans explanation. He does not burden her by asking for her forgiveness.

And then there are Tupac’s closing words:

I Don’t Know How you feel
About visiting me 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. [heart]

• apologies
• celebrities
• letters
• Madonna
• movies
• music
• Tupac Shakur

Revisiting “Juice,” 25 years later

It’s been a (very!) eventful two weeks, but I still can’t stop thinking about Hanif Willis-Abdurraqib’s terrific appreciation of Ernest Dickerson’s 1992 film Juice. That’s as good a reason as any to share it here.

Juice might be Tupac Shakur’s signature performance as an actor: he’s charming and frustrating, thoughtful and thoughtless — accelerating through emotions and personalities like an athlete changing speed mid-play — beautiful and wrathful and doomed, like Achilles or James Dean. Or, like Tupac.

Willis-Abdurraqib zeroes in a key part of the story, and of the best art from the era in which the film was made — “what so rarely happens with black people who live and die and do wrong today: an ability to visualize a complete life behind simply a finger that pulls a trigger, and a willingness to understand what drove them there.”

Juice came at a time when the black nihilist was being visualized and reconsidered onscreen in ways that had traditionally been afforded to and reheated for white actors and their stories. Movies like New Jack City, Menace II Society, and Boyz n the Hood showed black characters who either gained things with no moral code, or who were deeply aware of how little they had to live for, and conducted themselves in a manner that showed that awareness regardless of whom it hurt. These characters were sometimes sympathetic and complex, but none were like Tupac’s Bishop — in part because it was Tupac playing the role, but also because of the way we find Bishop, and how he ends up. By the time I was old enough to understand the emotion of his narrative, when I watched Bishop fall from the rooftop and heard the sound of a body hitting concrete that followed, I felt like I had lost a friend — a friend who, like some of my actual friends, had drifted into the machinery of some vice and had not felt loved or seen enough to shake their way out of it…

A tragedy is defined by the fatal flaw that plagues its central character, and the ways in which that flaw echoes down to all the other characters, leading to a brief and immediate reversal of fortune. The Greeks referred to this kind of flaw as hamartia — literally, a missing of the mark. Hamartia is to aim for a target and not hit it, and to have yourself end up on the other side of tragedy. It is, perhaps, to aim a gun at someone you want to kill and then pull the trigger, hitting them instead in an arm that they will soon need to pull your body back to safety. The true reversal of fortune rests in the brief moment before Bishop falls to the ground, when you realize that Quincy wants to save him, but can’t.

I should add, especially for readers who’ve never seen it, that Juice is beautiful. Dickerson was/is one of the best cinematographers alive before he became a director, and it shows. And the soundtrack is amazing. You could say it was a forgotten movie, but it’s just so unforgettable.

• Ernest Dickerson
• hip-hop
• movies
• tragedy
• Tupac Shakur