King of Pain: 20 Years Later, Tupac Shakur’s Problematic Genius Still Haunts Us

Tupac flanked by the Notorious B.I.G. (left) and Redman backstage at a Tupac  performance at the Palladium in New York on July 23, 1993.
Al Pereira/Michael Ochs Archives/Getty Images
Tupac flanked by the Notorious B.I.G. (left) and Redman backstage at a Tupac performance at the Palladium in New York on July 23, 1993.
Al Pereira/Michael Ochs Archives/Getty Images

To all the seeds that follow me
Protect your essence/
Born with less, but you still precious —Tupac

The aphorism goes, “Stars are born, not made.” I understood this twice in childhood: the first time I saw Magic Johnson on television, and the moment in Digital Underground’s “Same Song” video when a resplendent Tupac Shakur burst into the public consciousness on a chariot, wearing a dashiki and kufi, and holding a scepter that looked like it was fashioned out of black cool itself:

Now I clown around when I hang around with the Underground
Girls who used to frown, say I’m down when I come around
Gas me and when they passed me they used to dis me
Harass me but now they ask me if they can kiss me …

When I rewatched the video last week, it struck me that the men carrying the chariot looked like pallbearers. Even in his figurative birth as a star, his inevitably early demise winked at us. The two always moved hand in hand.


Tupac has been dead 20 years, which is nearly as long as he was physically with us on this earth, Cuban exile theories notwithstanding. Even as I wrote that, knowing it to be fact, I felt an instinctive skepticism because Tupac has transcended celebrity to cultural ubiquity. “Hail Mary” is Michael B. Jordan’s ring-entrance music in Creed; I was ambushed by “Dear Mama” while watching Mr. Robot. My close friend Justin coaches a youth basketball travel team out of New York, and he told me that a trend among black teenagers with whom he deals is the sporting of T-shirts for movies in which Tupac starred.

His legacy is as surreal as it is persistent: A statue of Tupac built by Italian artist Paolo Chiasera popped up at the Marta Museum in Herford, Germany; classes on his songs and poems have appeared in the course catalog at Cal Berkeley and the University of Washington, among many other institutions of higher learning; last year, a white woman from small-town Nebraska recalled to me each member of her sixth-grade class being tasked with reporting on a song that held particular significance in their lives—and half the class explained their love for the song “Changes”; a Tupac biopic is slated for release later this year; Johnny Depp is negotiating to star in a Tupac-related film; and they’ve even produced a Tupac movie in China.

Add in the innumerable posthumous albums and bootleg compilations, and Tupac is in the ultrararefied air of artists and celebrities more prolific in death than in life.

That’s saying a lot, given how prolific he was in life. In such a brief time, he managed to live what seemed even at the time to be nine different lives. Those of us near his age when he died are now in our 40s, or knocking at the door of that middle decade of life.

We are either still searching for our great achievement or hanging our hats on the one of two major accomplishments under our belts. Which makes it all the more incomprehensible to process Tupac’s output of six albums and six feature films (including two iconic roles) by 25. And that’s including the time he lost while recovering from a shooting and then a stint in jail. It strikes one as unfathomable that he slept before his final, permanent rest.


Scientific American says a star is born when atoms of light elements are pressured significantly enough to undergo fusion. The same article notes that all stars are the result of a balance of forces; that once fusion is achieved, stars exert an outward pressure. As long as the inward and outward forces are of equal intensity, the star remains stable.

Tupac epitomized fusion—cultural fusion—and maybe because of that, his star was never a stable one. The intensity of society he absorbed at every stop and the intensity he projected back at it were rarely in step.


He spent the first decade of his life in Harlem, the next four years in Baltimore, and came of age in Oakland, Calif., before his celebrity put him in a state of constant transience, living on the road, in Los Angeles, and in a jail cell. He was at once everyone and no one; as rich in spirit as he was, he was also spiritually homeless. That made him quintessentially black in America.

He was and remains a Jesus figure for so many black men, not because of his Makaveli album-cover art, but because he let himself belong to us. His love, his pain, his anger, his intensity, his generosity, his recklessness, his paranoia, his vulnerability … he put it all on display.


He was as naked an artist as I have ever known. No one had offered such access to his life, and the more titillating episodes made us wonder if he hadn’t entered a self-perpetuating cycle—it was tough to tell whether the music was being driven by his life experiences or was driving them. To some, he was hip-hop’s great method actor; to many others, he was the realest.

His energy was frenetic, his enthusiasm infectious. I could never figure out if he was running from or running toward something, but I knew I was willing to follow him wherever the journey took him, and me. The journey, in Taoist fashion, turned out to be the destination. In retrospect, I wish he had kept more of himself for himself. It’s not coincidental that he hasn’t even been allowed his own death.

Hit the bar and played the star everywhere I went
In my heart I felt alone out here on my own
I close my eyes and picture home
On my block

Everything about Tupac belonged to us in the end. In a very figurative sense, he died for the sins of our society and our culture of celebrity worship, violence, crass materialism and black death.


All these years later, Tupac is whoever we decide he is. He still functions as a funhouse mirror, and whatever we project onto him comes back to us in a larger, stranger reflection. He was a prophet, a player, a thug, a poet, a Panther, a prince. He navigated Nate Parker’s path of sexual assault but came out largely unscathed in terms of public perception. Most of us were always willing to give Tupac the benefit of the doubt, partially because he was handsome, irrepressible and charismatic, but mostly because he was a black man who loved himself because of his blackness rather than in spite of it.

He was also a hood folk hero come to life: He shot police officers who were harassing black men; he publicly went to war with gangsters; he danced with old women in wheelchairs; he passed out Thanksgiving meals. He was every stereotype of a black man rolled into one, a beautiful mess within which just about anyone could see himself, somewhere.


As a rapper, he changed so much about the genre that it’s difficult to quantify. After Tupac, seemingly every rapper had tattoos from head to toe; seemingly everyone has mimicked his gratuitous ad-libbing and rants; seemingly every diss track since “Hit ’Em Up” has aimed for deeply personal insults that cross lines of basic decency.

But all of those things seem cartoonish in Tupac’s wake, because everything he did was so extreme as to render any facsimile of his way of being contrived and absurd. His reverence among other rappers is unparalleled. 50 Cent came out of the gate professing a desire to have rap fans love him like they love Pac; even rap luminary Nas dressed up as Tupac, sporting a Pac-inspired tattoo across his belly to pay tribute at an award show.


Just as every rapper seems to have borrowed something from Tupac, everyone has a Tupac story:  Tony Danza, Nikki Giovanni, Mickey Rourke, Jasmine Guy, Jada Pinkett Smith, Madonna. The list goes on and on and on. My blood cousin is Kool Keith, and I remember sitting on his tour bus in 2003, shaking my head in a mix of astonishment and humor while his since-deceased friend and collaborator Tim Dog shared a story about Tupac saving his life in San Francisco.

I have my own Tupac story. He used to hang in my Harlem neighborhood from time to time; his wife, Keisha Morris (the marriage was annulled), lived in the building down the block from my cousin Booby, and Tupac would also come through to check on Ra-Ra who lived (I think) in the Jackie Robinson projects. At that time, Ra-Ra was a young boy who was featured on the last track of Me Against the World.


One night, Tupac was hanging with a group of older guys from my cousin’s building who were block legends; I was young, so when my cousin Booby pointed them out, I played it low-key. They were drinking and smoking while leaning against a bodega wall on 126th and Lexington, across from where Sal's candy and video game spot used to be.

One guy started freestyling and was trying to get Tupac to join in. Tupac just smiled and laughed and said he would rather just hear him rap. He told him he was good at rapping, and called him "that verbal [n—ga]" when he was saying his goodbyes. I could tell, even from a distance, that Tupac had the glow. And his presence in that neighborhood was the reason that when the East Coast-West Coast beef was heating up and so much of New York hated Tupac, Harlem always had love for him, and you'd hear his music there all the time.


And when the music was good, it was wonderful, grim as it was. He drew from the same misogynistic, violent and materialistic well as all the rest, but in his hands, even the cliché was infused with an energy and meaning that transcended the lyrics.

And when he was truly in his bag, he made ballads for the dispossessed. Those songs don’t share the intellectual heft of a James Baldwin essay, but they have the same eerie quality of persistent relevance, which says as much about the cyclical indecency, classism and racism of American society as it does about his insights into it.

It's kinda hard to be optimistic
When your homie's lyin dead on the pavement twisted
Y'all don't hear me though, I'm tryin hard to make amends
But I'm losin all my motherf—kin friends

Like many young black men, I wept openly when Tupac died. I didn’t cry because he was a prophet or a hero or the second coming of Malcolm X.  Our mythologizing of Tupac as genius and revolutionary is rooted less in reality than in the depressing circumstances of black life in America. The reality that so many of our brilliant leaders and revolutionaries were systematically murdered before, during and just after the civil rights movement, we are a rudderless ship, constantly seeking a captain to steady us. In a society that has killed so many of our heroes, and told us in so many ways that we are inferior citizens, we’re starved for someone to step into the leadership void.


Tupac wasn’t our leader, he wasn’t our freedom fighter. He was as problematic as he was persuasive and poetic. To erase that side of his legacy is to neuter it; his power was rooted in the intense swing between the life and death instincts, the yin and the yang, the remarkable and the lamentable. He doesn’t have to be sanitized and misremembered as Malcolm X or Marvin Gaye. Tupac was our superstar. He still is.

Right before I die I'll be cursing the law
Reincarnated… even worse than before

That evening on a Harlem street corner, about 25 years ago, I saw our superstar, and he glowed, even in his relative silence. Back then, I couldn’t see that the future of the Harlem I knew was even bleaker than I thought: that in another seven years, 125th wouldn’t even have a hint of its old life to it; that vendors and bootleggers would get harassed out of existence; that the iconic eateries and record shops of my youth would be forced to close; that the people who used to show up on tour buses to eat at Sylvia's and gawk at how the other half lived would soon show up in moving vans and turn Harlem out with gentrification. That across from Ra-Ra’s Jackie Robinson projects, in front of the enormous wall that had "EACH ONE TEACH ONEgraffitied across it for years, where we would play taps until, like, 2 or 3 in the morning because there were lights on the basketball court, there’d be a repast for my cousin Booby after he’d been shot and killed, too.


I cried again while writing this because Tupac is gone, my cousin Booby is gone and the Harlem I knew is gone. Most of all, I cried because so many black men in America die young or see their hearts and souls age prematurely, and that’s why I understood and loved Tupac’s music, and all its paranoia, weariness and death.

I cried because historically, just about all black music is about finding a way to distill a tiny bit of happiness from unspeakable misery. I cried because, like Tupac, black people are perpetually homeless and unstable in America, yet we persist, we transcend and—against all odds—we rise.


T.D. Williams was born and raised in New York City, where he spent his youth in a welfare hotel for the homeless in Times Square. He has been a soda salesperson, camp counselor, a parking lot attendant, a waiter, a bartender, a civil rights activist, a dean of college admissions and an adjunct professor. He is currently finishing his first novel, and his writing on sports and societal issues has appeared in various publications, including Sports Illustrated. Follow him on Twitter.