I Ain’t Mad at Cha

On Tupac’s letter to Madonna from prison, and their complex romantic relationship mediated by race, sexualization, and fame.

By Shawn WenAugust 9, 2026

• Music

• Gender & Sexuality

• Television

ON AUGUST 10, the trial for Tupac Shakur’s murder is expected to begin. Nearly 30 years after the rapper was shot in a drive-by, Tupac’s death and all that he left behind—a catalog of unreleased music, lyrics that read like prophecy—still generate wide-ranging speculation and fringe theories. Was the hit ordered by Biggie, Sean Combs, Suge Knight, or the US government? Is he still alive somewhere in hiding? What we will miss in all the speculation about this near-mythological figure and his untimely death is a more intimate Tupac—a partner, a lover, a man who left behind a letter holding clues to how he thought and loved, and how that love was made impossible.

On January 15, 1995, a year and a half before he died, Tupac wrote pop star Madonna a letter from prison on a yellow legal pad. Although they kept their relationship a secret at the time, Madonna has since confirmed their involvement. In the top right margin of the letter, he noted the time as 4:30 a.m., as though he wanted her to know that he had stayed up late thinking about her. He explains the strain that their romantic relationship caused him—the inevitable misunderstandings of interracial relationships when one person is from the dominant group and the other is not. But first he felt it necessary to tend to Madonna’s feelings.

Tupac addressed her intimately as “M.” “[S]ome of it couldn’t wait. I felt compelled to tell you … Just in case anything happened 2 me.” He wrote a long apology, expressing regret for how he had ended their relationship: “I never meant to hurt you. As a matter of fact I was honestly stuck on you but I got scared.” He went on to explain that if their relationship had gone public, it would have reflected differently on each of them: “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 & exciting. But for me […] I would be letting down half of the people who made me what I thought I was.”

In other words: A white woman’s choice of loving a Black man is a reflection of her individuality, but a Black man’s choice of loving a white woman could be seen as a rejection of his own race. And it’s not just love. Every choice a Black man makes can be interpreted as a reflection upon his relationship with race, with his entire community.

“It always hurts when it’s one of your own,” a Black co-worker said to me when we were riding in his car as news broke on the radio about an Asian cop killing a Black man. We both laughed at his joke, which cut both ways, lacerating each of us. Because it’s true. When an Asian person acts with brutality, or becomes a victim of violence, or wins an Oscar, it reflects on every Asian person in the United States. It reflects on me. And my co-worker, a Black man, of course had an untold number of things reflected upon him. But somehow white people still escape this burden.

The idea that whiteness grants individuality while non-whiteness imposes a representational burden is not new; it’s a conversation we hear a lot. But Tupac’s letter, along with a contemporaneous appearance by Madonna on the Late Show with David Letterman, shows us how this operated in real time for two of the most famous people of the 1990s. At the time, she was 36, and he was 23. He puts it bluntly to Madonna: “[A]t the risk of sounding over dramatic, the effects of racism make it difficult for a young Black male to properly show affection for an older white woman. Can u understand that?”

A man in prison, writing to a woman he loved, explaining that his race made their love impossible, and begging her to understand. And she seemed not to understand. In fact, she made it worse.

There are a handful of photos of Tupac and Madonna taken earlier in the year before he wrote this letter. I like to think they were in the thick of their romance. They were seated next to each other at a book release party for Versace in New York. Their wardrobes mirrored each other, both dressed in sweaters, with chains around their necks (hers was bigger) and piercings in their left nostrils. They leaned toward each other so closely that their arms were slightly touching. They look as if they were trying to suppress wide, silly smiles. I imagine the secrecy of their relationship had not turned destructive yet but was still sweet and tantalizing.

In his letter sent from prison, after he apologized to Madonna for hurting her, Tupac told her that she had bruised him too:

I read somewhere in an interview where you said “I’m off to rehabilitate all the rappers & 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. 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 I have since come to regret.

While we have Tupac, in his own words, taking accountability for inflicting pain, it’s unclear if Madonna ever did the same—if she ever apologized for the wounding sentence he references. For how she bragged about her association with “rappers & basketball players” knowing that it added to her social capital. For how she used “rappers & basketball players” as a stand-in for Black men, collapsing Tupac into an entire category of people who needed “rehabilitation” through her. Tupac understood that their relationship represented a loss in social capital for him and a gain for her.

Tupac is referencing Madonna’s surprise appearance on The Tonight Show with Jay Leno in May 1994, the same year she presumably dated the rapper. Saying her goodbyes to Leno, Madonna jokes about where she’s headed after the taping: “I started this organization that rehabilitates rappers and basketball players […] and there’s just so much work to be done.” She’d stopped by Leno’s studio presumably as a PR move after a controversial interview with David Letterman a month earlier. The infamous Letterman conversation was best remembered for Madonna’s saying “fuck” 14 times during the segment, smoking a cigar onstage, and getting booed by the audience. In the brief Leno interview, she makes repeated references to her Letterman appearance, from her opening salvo (“Can I just say that it’s so nice to have a real gentleman in New York City?”) to her response to a question about her love life (“It just makes me want to say the f-word over and over again”).

While she’s talking to Leno, the Letterman appearance is clearly at the forefront of her mind. When I watched the earlier interview, I was shocked, much like the studio audience, but not by Madonna’s cursing. I was shocked by Letterman’s treatment of Madonna—which at times is relentlessly sexualizing and harassing—and also by how she uses race to fend him off.

Before she walks onstage, Letterman introduces her: “Our first guest tonight is one of the biggest stars in the world. In the past 10 years, she has sold over 80 million albums, starred in countless films and slept with some of the biggest names in the entertainment industry.”

She walks onto Letterman’s stage wearing a black slip dress and combat boots. Her hair is dyed black and slicked back. “I’m only here ’cause there isn’t a Knicks game,” she says, as she takes her seat in an armchair beside Letterman’s desk.

In those days, Madonna was a regular at Knicks games. She had told USA Today she had “a big interest” in buying an NBA team, though when she elaborated on that interest, it appeared primarily sexual.

“I had a crush on all the players […] You can see the guys’ legs and arms and faces. They’re so graceful. And it’s so in-your-face, so intimate.”

“Would you be a hands-on owner?” the USA Today reporter asked.

“Definitely,” she replied. “My hands would be all over the place.”

On Letterman, Madonna sometimes participates in her own sexualization, and sometimes she pushes back. By 1994, this contradiction was central to her public identity. For more than a decade, from the “Like a Virgin” performance at the 1984 MTV Video Music Awards through her 1991 documentary, Madonna: Truth or Dare, and her 1992 book, Sex, Madonna presented herself as an iconoclast, waving the banners of sexual agency and transgression. She made enemies with the Vatican, broadcast censors, and the American religious Right. She turned herself into a site of fierce cultural debate, polarizing feminist critics who argued that she was either the “future of feminism” (Camille Paglia) or a “glamorized fuckdoll” (the label used by Pamela Robertson to capture the criticism). But what both sides of this debate miss is what Tupac’s letter makes visible: whatever power Madonna wielded over her own sexual narrative (or not), she did so, in part, by instrumentalizing Black men. We can see this play out on Letterman.

Letterman goads her. “Let’s go kiss a guy in the audience. Why don’t you go kiss a guy in the audience?”

“Why are you so obsessed with my sex life?” she asks.

“Go kiss the guy in the audience. It would knock him out,” Letterman insists.

Madonna squirms and touches her hair. She crosses her arms in front of her. She’s laughing, and her smile is so magnetic that I almost believe she’s having fun during the taping, but her body language reads as uncomfortable to me, and her words are furious: “Incidentally, you are a sick fuck. I don’t know why I get so much shit. You’re twisted.” Madonna’s foul language is what this interview is remembered for. Later in the interview, she says, “[Y]ou are always fucking with me on the show. You are always fucking with me on the show.” She repeats it a third time. “You are always fucking with me on the show.” This taping, of course, happened decades before the Me Too movement. These days, we can clearly see a powerful man harassing a woman on national TV, enjoying taking her down a notch, sexualizing and objectifying her, as the audience laughs. But are we ready to understand the white woman’s response?

Madonna has a few tactics that she switches between. She insults Letterman, asks if his hair is a wig, calls him unfunny. She asserts herself as a sexual being, demanding he sniff her panties and inviting him to touch her dress, and she does this so boldly that Letterman demurs. She also sexualizes Black men as a way to regain power in the conversation.

Letterman asks her, “Are you buying an NBA team?” Madonna says no, and he continues: “How come? […] But you like basketball.”

She looks up toward the ceiling and gestures at the boom pole above her head. “That microphone is really long. Speaking of the NBA.” She is smiling now, licking her teeth, grinning at her own double entendre.

Letterman tries to refocus the conversation: “So now let’s talk about your interest in the NBA. You go to a lot of games. You were friends with Charles Barkley.”

She responds, “I don’t think he understands the meaning of friendship.”

“He seems like he might be a hothead, that guy.”

Madonna is quiet for a moment, and then she slowly moans, “Mmmm. Mmmmhmmm.” She pushes her tongue against her lips, making her mouth appear to swell, making a display of her deep red lipstick.

“Did you know him at all?”

She smiles as if to say yes, “Mmmhmmm. Yeah.” But she doesn’t elaborate.

Madonna’s tactic here—sexualizing Barkley as a way to frustrate Letterman—eerily plays out a prescient moment from the Black feminist critic bell hooks’s essay “Madonna: Plantation Mistress or Soul Sister?” Writing in 1992, hooks decries the lack of racial critiques of Madonna, and particularly the “Like a Prayer” music video, in which she kisses a Black saint:

No article called attention to the fact that Madonna flaunts her sexual agency by suggesting that she is breaking the ties that bind her as a white girl to white patriarchy, and establishing ties with black men. She, however, and not black men, does the choosing. The message is directed at white men.

On Letterman, in real time, you can see Madonna attempting to regain her agency with this exact strategy. She does what she has been both celebrated and criticized for—seizes control of the sexual narrative—but her sexual agency here, in this moment, is built on the bodies of Black men.

Letterman gestures at her nose ring, “Did it hurt when you had that thing put in your nose?” He tries to bring the conversation back to her, but Madonna refuses to let him.

She cackles and becomes more animated. “I thought you were going to ask me if it hurt something else […] I thought you were going to continue the Charles Barkley line of questioning. […] And the answer is […] yes.”

Letterman shifts back to the nose ring. “What happens when you take that out?”

“The answer is yes. Both questions.”

Madonna’s interview with Letterman not only made it the most-censored episode in talk show history but also earned him some of the highest ratings he had ever received.

“Now when you leave here tonight, what are you going to do? Are you gonna go out?”

“Don’t fuck with me, Dave.”

Letterman makes another joke, this time asking to kiss her. “If I don’t have to wait in line,” he says.

“Well, you’re not in the NBA, so forget about it.”

Over the course of 20 minutes, Madonna complicates the long feminist debate about who is in control of her sexual image. She wrests control from Letterman, but she does it by perpetuating sexual mythologies about Black men. And her boyfriend, at the time, may have been watching.

“Do you have a boyfriend? Are you currently interested in someone? […] What’s his name?”

After a beat, she says, “Dave,” deflecting him with another joke.

Before her answer, she stares off blankly into the middle distance. Her eyes look almost wistful. She does have a boyfriend and it’s unclear if she realizes how much she might have hurt him in this interview. Two decades later, Madonna confirmed the relationship on The Howard Stern Show. When Stern asked about her behavior on Letterman that night, she said, “I was in a weird mood that day. I was dating Tupac Shakur at the time, and […] he got me all riled up about life in general. So when I went on [Letterman’s] show, I was feeling very gangster.” Funny choice of word, “gangster.” She co-opted a word that had been forced upon Tupac. Tupac in her telling is a stereotype, a mood she was in, a passing phase.

Discussing Madonna kissing a saintly Black figure in the “Like a Prayer” video, bell hooks, again, wrote, “That Madonna’s chosen prince was a black man is in part what made the representation potentially shocking and provocative to a white supremacist audience. Yet her attempt to exploit and transgress traditional racial taboos was rarely commented on.” In these cases, her audiences were Letterman and Stern. Her associations with Barkley and Tupac—indeed in Tupac’s own words—made her “seem that much more open & exciting.”

Perhaps Tupac felt the cumulative weight of her innuendos here and elsewhere and compressed them into his feeling that she had reduced him to a stereotype, that she was “off to rehabilitate all the rappers & basketball players.” Madonna framed herself as an individual, against a backdrop of Black men. She was one of a kind, and Tupac was one of many, a demographic reduced to “rappers & basketball players.” He objected to this framing: “[Y]our words cut me deep seeing how I had never known you to be with any rappers besides myself.”

Madonna’s chosen framing extends to their legacies. She is the Queen of Pop, shocking for her bold sexual provocations, a master at reinventing herself. Tupac’s music articulates the heritage, social issues, and injustices borne by generations of African Americans. His image is iconic too, but he bears the burden of representing an entire racial group. Madonna has been free to be herself, That Girl, for over 40 years now.

This persistent individuality is what I envy most in white people. Their failures and successes are all their own. They represent only themselves when they show up to work and school. The famous among them shrug nonchalantly: “I don’t want to be a role model.”

Every person of color who moves through white spaces hears a near-constant refrain: “You aren’t like other [____] people.” This is intimated as if it’s a great compliment. Sometimes it is phrased as a question, asked with genuine curiosity: “Why aren’t you like other [____] people?” We learn to shrug it off. There’s no answer for these questions, and it feels inadequate to reply “I am an individual just like you.” I wonder how often white people say to one another “You aren’t like other white people.” Is it automatically assumed that each white person is unique?

Tupac wanted his romance with Madonna to be that of one person loving one other person, rather than one person loving a stereotype. “It no longer matters how I’m perceived,” Tupac wrote to Madonna. He wanted to heal things: “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.” Next to these words, he drew a little heart. His words are so tender. So forgiving. He beseeches her to come to him. A Black man in prison, forced to play the stereotype of a gangster, writing on a yellow legal pad at 4:30 in the morning, drawing a small heart in the margins. “Can u understand[?]”

¤

Featured image: Still from Madonna interview on CBS’s Late Show with David Letterman, March 31, 1994. Image has been cropped.