In 2015, Madonna sat down for a Howard Stern interview. She actually gossiped a lot and made some news with some of her revelations, like she dated Jean-Michel Basquiat but dumped him because of his heroin addiction. She also said that she dated Tupac for a moment in the ‘90s, which was news to me at the time. I didn’t even know that Pac and Madge traveled in any of the same circles back then, but apparently they did, they went to the same parties and they had friends in common. They met, spend time together, dated briefly and then… Tupac dumped her. Because she’s white!! Apparently, when Tupac was in jail in 1995, he broke up with Madonna by writing her a Dear-John type of letter, explaining his reasoning.
On Wednesday, TMZ published portions of a letter—written Jan. 15, 1995 at 4:30 a.m.—that Tupac wrote to Madonna while serving time for sexual assault at Clinton Correctional Facility. Gotta Have Rock and Roll will auction off the letter between July 19-28 with a starting bid of $100,000; according to TMZ, the last letter written by the rapper fetched more than $170,000. TMZ redacted four chunks from Tupac’s letter. The late rapper started by calling Madonna “M,” saying, “I’ve waited a long time 2 finally write this mainly because I was struggling to find all the answers that I wouldn’t leave any unanswered questions. First and foremost, I must apologize to you because like you said I haven’t been the kind of friends I know I am capable of being.”
Later in the letter, he explained that he broke up with the “Human Nature” singer because of her race. “Can u understand that? 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,” he wrote. “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 went on to reference an interview where Madonna had supposedly said, “‘I’m off to rehabilitate all the rappers & basketball players,'” or something like that. “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.” After another redacted paragraph, Tupac continued to share his side of the story with Madonna. “Can you feel me? In the time since, as u can see, I have grown both spiritually and mentally. It no longer matters how I’m perceived,” he said. “Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol.”
Later in the letter, the hip-hop heavyweight wrote, “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.”
Tupac ended his letter with a warning for the Queen of Pop. “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!”After signing the letter, he added a final message: “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,” Tupac, who was fatally shot, said. “It’s funny but this experience has taught me to not take time 4 granted.”
You know what? I have to give it to Madonna – whenever she’s name-dropping and humblebragging, I always think “you are so full of sh-t, Madge.” But she’s actually telling the truth about so much of this stuff. She really did date Tupac. They really did have a connection, enough of a connection where Tupac had to write her a long-ass Dear John letter explaining why he was dumping her. And I totally get his reasons too, because Madonna was, like, Peak Clueless White Woman (I cringe when I think about what she probably said to Tupac, much less what she said about him) and Peak Culture Vulture at that point. Dating Tupac gave her a certain kind of “credibility” where it was probably nothing but a major pain in the ass for him. Still, it’s clear that he cared about her.
Photos courtesy of Getty.
I’m wondering why TMZ redacted parts of the letter. They’re not known for restraint.
I’m guessing because it’s up for auction – if you can read the whole thing online, why spend money?
He shows more talent in one letter than many artists today can produce in 3 albums. Such a phenomenal writer.
Yay with the vintage gossip, love these!
So agree.
I love letters.. I hate that we are now reduced to 140 characters. I miss getting letters in the mail. I’m getting OLD.. but damn letter writing is a talent.
I’m shocked by the heart and soul in his words. He’s so beautifully expressive!
He was always so good with words. So soulful in general.
To find that he was a thug and a gangstar was really shocking because it went against the soulful, thoughful words and poetry.
He had real talent, and this letter shows how much thought he put into it and how perceptive he was. He was a true artist and I get sad when I think of rap music today vs then, most of it is meaningless bullshit singing about white tees or stilettos, not all of Tupac’s music was deep but man it was so much better than anyone today by far.
My impression, as well. On top of the huge heart, he was so damn pretty, too.
I know Tupac is a legend and all…..but I can’t even see past the terrible grammar….geez!
But having said that, there is a lot of unexpected sensitivity in his thinking/writing
I call fake. This letter is fake and they never dated. They were just friends as he said in an interview.
Madonna pulled the same bs with MJ. She makes up stories about dead black superstars. She is a vulture.
I call matter of perspective of this… If you’re spending a lot of time together and you bang, some people will call it friendship and some people will call it dating. Either way, Madonna was a huge star and she dated everybody. Now, if you want to question whether she dated the people she claims she dated just to big up her profile, fine, but are you really doubting that, at the height of her sexual icon status, she slept with and was friends with a ton of famous people?
Pac clearly said their relationship wasn’t sexual and she never challenged that claim until he died. So yeah, I think she’s lying.
I remember this particular story. She was going through a famous black dudes phase, Kardashian style. Dated Dennis Rodman, Tupac, Lenny Kravitz or was he earlier.
I wasn’t surprised about Basquiat because there were so many rumours in the 80s about them. For some reason i thought Keith Haring too until i realised he was gay. Mind you, i thought Basquiat was gay, so there was confusion all round.
She never claimed to date MJ. That one Oscar date they had was mutual publicity stunt which was very obvious to everyone. At the time she was rumoured to have found him too strange in terms of his set up and didn’t take it any further which in itself was shocking because Madonna l-u-r-v-e-d the publicity their one date generated.
That’s right, she never claimed to date MJ. She just puts up pictures of him/them all over her social media like they were these special friends, except they didn’t like each other and she never supported him as a fellow superstar artist when he was in terrible situations (which is her right, but don’t use him now he’s dead, you know? Keep shutting up like when he was alive.)
Black man phase made me giggle a bit. I’ve dated different races and ethnicities. I’ve even dated three White man back to back. Does that mean I was going through a White man phase since I’m Black . Wait, I was, just kidding. I’ve dated plenty of White men but it wasnt a phase. I date based on atttaction, not race.
Bit it is a bit suspicious that she is talking about this now that Pac is back in the limelight with his recent film in theaters “All Eyez on Me.”
I can believe they dated for a bit. The thing I find interesting about madonna when she speaks about ex lovers or collaborators is it’s usually the gorgeous and talented ones. She doesn’t say a lot about the relationship she had with Vanilla Ice.
I can believe they dated. But after reading that letter, I’m wondering how any man managed to stay interested in her for more than 2 minutes. “Rehabilitating the rappers and basketball players?” What? Condescending, much?
I can see why he dumped her.
If I was ‘Pac I would have jumped on Raquel instead of Madge. Now THAT was a woman…
I love his music but why are people still “worshipping” him to this date?
He was convicted of sexual assault and was in a rehab facility in New York for the crime.
I totally get where he is coming from but it seems to me he was more worried about his reputation amongst black people than he personal happiness.
He was later vindicated for that sexual assault charge because the “victim” admitted it was a set-up in full details as to who set him up and why they set him up. She came forward after his death, but there were even receipts presented with other witnesses to the setup. So to answer your question Tupac is “worshipped” or respected because his message was deeper than rappers at the time and he was truly a revolutionary in his thought, raps and actions towards uplifting black people. He had Black Panther roots and it showed in his rhymes and interviews. And real fans already knew the sexual assault charge was fake.
What about when he shot a 6 year old? Pac had a deeper message but he was still conflicted, he wanted to be rise above but was also dragged back in frequently.
The U.S. for pointing that out. People tend to point out his sexual assault case but leave out the part where it was proven to be false and the woman lied.
@UmYeah he didn’t shoot a 6 yo. Video of the park shooting is available if you want to see. By all witness accounts, Pac did not have a gun nor did he directly or indirectly cause that child’s death. He was in a fight, caused by the other party, and another person pulled out a gun and shot. That death was instrumental in his development, so it is important to get the facts straight.
V4Real it really upsets me that the gossip machine keeps perpetuating the lie that Tupac was convicted of rape. Not only is that not true but it has been proven to be a lie.
@AmunetMaat can you drop a link for the video, i have seen videos of the performance but not the shooting? I know the bullet that killed that little boy on that afternoon was linked to a gun owned by Tupac. Sometimes when people die, famous or not, people like make them out as saints. I always thought Tupac was very real, in constant conflict with who he was versus who he wanted to be, i can relate to that, i think most people can relate to that.
I can’t find any comments from the victim saying her allegations were false, just an interview from 5 years ago where she states that she did think that the police went after Tupac particularly because of his reputation, and that that was damaging to her too because she as the victim was treated badly by the police, an afterthought, and no one cared about the other men who assaulted her either. It was all about Tupac.
I can’t find anything confirming any of it was a lie, just a bunch of crackpot nonsense about how the FBI spent years planning this set-up, along with Mike Tyson’s.
No, the victim did not recant her testimony. Please stop perpetuating a lie. I understand Tupac’s influence on culture and society. And he was flawed like all humans. But please stop disrespecting a victim because it doesn’t suit your narrative.
@Amunet
The fact remains that he was convicted of sexual assault and did time in prison for it , whether you believe he did it or not and the woman did not recant that is some fan fiction she said it became all about Pac instead of her and the other men who raped her
From what I understand the story has some parallel to Nate Parker in that the girl liked Pac was there for him and had consensual , sex with him earlier. In this later instance his boys took that as an opportunity to run a train I.e gang rape her
Even though Pac has steadfastly mantained his innocence he admits that he should not have walked away and let his boys do what they did as he suspected she was not t down for that .he said basically his only regret from that night was that he didn’t want to seem weak or punk out with his boys by putting a stop to what he knew was going to go down
I mean… yeah. And I feel like he didn’t break up with Madonna because she’s white, but because she’s *white.* I hope this doesn’t sound terrible, but Madonna is hella white, in the way that it’s more of a personality trait than a racial identifier. Clueless, ridiculous, and slightly desperate. I say this as a white woman, because some white people, man… I just can’t.
Kathleen at Lainey has a great analysis of this same perspective @Shambles- that most reporters and bloggers are looking at the letter without any depth, and not actually reading into what he is saying about the challenges an inter-racial relationship would pose for him with his image and his fans. He isn’t wrong, and he’s very thoughtful about the dialogue he is having about it.
Looking at any relationship with any depth, I think if you really truly care about someone, you won’t give a second thought to what everyone else thinks. Especially for something as superficial as skin color. Values, for some reason, get discussed much less in these types of discussions than skin color does. Finding someone whose values align with yours is the vital thing, I believe.
I find it hard to believe that if this letter was ever in Madonna’s possession that she would’ve lost it or given it up. Seems weird.
Yes that’s the part that I don’t understand at all. Where did this suddenly materialize?
But I love his writing
Did not know he was a convicted rapist until yesterday
He wasn’t convicted of rape, they couldn’t prove that rape occurred. Instead, he was convicted for inappropriate touching. That charge was disputable.
Is Madonna the one auctioning it off? If not, how did it leave her possession? Did she authenticate it? Lots of questions, not a lot of possible answers which aren’t distasteful.
Maybe it’s a copy the prison took? I’d think that all letters convicts write are copied and stored, but I don’t know that for a fact.
It’s your typical, it’s not you, it’s me blow off.
I could see it happen. Madonna was an icon and a very sexy and confident women at the height of her celebrity, constantly reeinventing herself in an organic way, that would surprise you.
It is a shame that she has not been able to handle aging with the same style.
If someone was breaking up with Tupac cos he’s black, nobody would be cheering them on the way the comments are super understanding of Tupacs move.
I hate when people do this. Roles can’t simply be reversed and equated. What don’t you get about that? The racial and social politics of the time need to be considered and Madonna’s “whiteness” was a part of the problem. Who in the hell is she to rehabilitate rappers? That speaks of white privilege so yeah . . . she needs to be dumped because she’s that type of white.
I dont think Madonna was trying to “rehabilitate” Tupac, i think she was attracted to him and his talent. Madonna had already courted controversary with her “like a prayer” music video, she wasnt afraid of negative press and liked to push the boundaries.
I agree you can’t reverse roles. Things were more segerated at thhat time in terms of music and popular culture. Tupac wasn’t just another rapper, he became symbolic to a lot of black people for actually bridging the gap between conscious rap of the late 80s to the hardcore street message of the early 90s. That means his blackness and what he did and how he handled his blackness was a part of his image or brand. Madonna’s brand was different, and she was going through a phase. Madonna has famously said each album is like a tattoo that it represents a phase of one’s life. Her album Bedtime Stories and Erotica was around the time she was culture vulturing black culture and being “shocking” dating black men was her way to do this. I remember the street convos at the time about it, like my mom was even commenting on it. It was the few times I recall her talking about Madonna. So for Tupac to date Madonna at that time when she was talking reckless was a problem for him and his brand. Also, he had clearly gone through a transformation of thought by this time in his career.
Seems like her words in an interview went against her, not simply her skin colour. I can see why he dumped her.
Anyway, maybe he instinctively knew he was being used for her image. And maybe he liked putting sugar in his tea. It’s not like skin colour is the only reason someone might not want to date Madonna, no matter how confident and vibrant she might be.
Because while y’all are busy “not seen color” we’re over here proud to be black and brown, and all that means in life, family, and community, in a world where white privilege means to strip it from us or use it to demean Who We Are.
The hour is too late in America to pretend like you don’t understand anymore.
It boosted her cred to be seen with him, it diminished his. She was playing counter culture, a big eff you to the conservatives who don’t like to see mixed couples. Very on brand for her
I imagine to see a major star date a white woman when he got famous, that might rub some people really wrong. It might have been troubling to him on a personal level as well, and it seems it was very off brand for him.
I was also a bit suprised, his letter showed an emotional maturity I didn’t expect.
Isn’t there a family missing their 6 year old child because of this guy?
No there isn’t. There is a family missing their 6 yo because a reckless person brought a gun to a park and decided to use it in a regular basic fist fight that they started. Tupac was not the guilty party in that poor child’s death as he did not start the altercation or bring a weapon to that alteractaion. Please stop spreading lies.
Actually the bullet came from a gun registered to Tupac
The little boy’s name was Qa’id Walker-Teal. He would be 25 years old now.
No, this is a lie. Tupac isn’t responsible in that poor kid’s death. But since people wants to talk about kids and families torn apart, what about those kids Madonna bought herself in malawi?
I was naming the victim. I was not assigning blame to any one individual. It was a tragedy that rocked Marin City. According to media at the time, Tupac apparently felt culpable and was very upset about this incident. A civil court found Tupac and his brother responsible in the wrongful death suit.
They have great lives.
I don’t doubt that they dated/slept together, everyone does that in Hollywood. But if this letter is real, how did it leave Madonna’s possession? Did she intentionally leak it to prove her claim? Why is some of the letter redacted? How did TMZ authenticate it? So many questions.
She has had hundreds of people working for her over the years. It could have been a cleaning lady, an assistant, a “friend”, anyone, who just found and took the letter without her knowing.
I get a feeling that Tupac was totally over her, but was wording his letter as carefully and caringly as possible because he did NOT want to be on the blacklist of the biggest popstar on the planet, since he was in the same industry.
I am under no illusion that he was this “good” guy. He had “girlfriends” all over the place and everyone knew, his own wife has admitted she knew about the other women.
But yeah, he was talented and played a big an important role in rap, and overall black culture. No doubt.
Maybe her skin colour didn’t help out the relationship, but I can also see a lot of other reasons why someone wouldn’t want to date Madonna over the long term.
If he was dating some other white lady, I tend to think the relationship might have lasted longer.
He was engaged to Kidada Jones, daughter of Quicy Jones. She was half white (mixed)
This is also a lie. This whole Kidada engagement idea only emerged years after his death, and nobody close to Pac would say she was much more than a casual girlfriend.
What Madonna told Howard in 2015 was no revelation! She didn’t present it like it was a revelation, either. Anyone who’d been paying attention already knew she dated Tupac. Even People magazine referenced it a decade ago: http://celebritybabies.people.com/2007/10/30/rumor-madonna-w/
Call me a cynic, but I think Madonna calculated to have a baby with someone outside her race just so seem exciting and hip, then after that was accomplished marry and have a kid with a white guy.
The pattern is apparent. When she turned 35 in 1993, Madonna decided she wanted to get pregnant and went on the prowl for a baby daddy. Look at the men she dated during that time: Tupac Shakur, Dennis Rodman, Jose Canseco, Jim Albright (her bodyguard), Carlos Leon…all ethnic. Months after having Lourdes, she kicked Carlos to the curb and started dating white men: Andy Bird, Mark McGrath, Guy Ritchie. And the rest, well, you know..
Anyone else make this observation?
Actually, Madonna was helping the FBI build a case against him as an informant. He found out. I think he wrote this to try to pacify her so she wouldn’t rat him out.