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‘60 Songs That Explain the ’90s’: Tupac Against the World

Rob breaks down the complicated life and indelible legacy of one of the most important figures hip-hop ever produced, including his megahit “California Love”

Grunge. Wu-Tang Clan. Radiohead. “Wonderwall.” The music of the ’90s was as exciting as it was diverse. But what does it say about the era—and why does it still matter? On our show 60 Songs That Explain the ’90s, Ringer music writer and ’90s survivor Rob Harvilla embarks on a quest to answer those questions, one track at a time. Follow and listen for free exclusively on Spotify. In Episode 58, we’re breaking down Tupac Shakur and his megahit “California Love.”


So, listen. I have dreaded the Tupac episode of this show for a year. For a calendar year. The weight of it—the emotional, the biographical weight of it. The towering monolith of excellent preexisting Tupac scholarship. Tupac is arguably the most photographed barn in America, while we’re getting all literary. That’s pretentious. One of the most famous, the most revered, the most reviled, the most extravagantly mourned rappers, entertainers, humans in recent American history. It’s a lot. He’s a lot. There’s a lot. We’re gonna get through this together.


Because Tupac is a lot, inevitably, we might ignore or briskly sidestep a lot. A few ground rules, then, I suppose. Other than right this second, I don’t expect the Notorious B.I.G. to come up much at all; just as, when we did a Notorious B.I.G. episode, Tupac didn’t come up much at all. That’s only fair. That feels symmetrical. I don’t mean to break the suspense but I will not be definitively solving Tupac’s murder at this time, nor for that matter will I discuss his death in grueling detail, or in any sort of detail whatsoever. I confess that I have very little time or patience or, quite frankly, emotional bandwidth for the Posthumous Tupac Industrial Complex, the 10,000 thrown-together albums, the hologram (ugh), the jukebox musical, the movies, the books (the books generally are really good), the NFTs, I assume. Should I Google “Tupac NFT”? I’m gonna regret this. Oh, they got NFTs of his jewelry collection. That’s, that’s—yeah. I regret that. The fuckin’ hologram. Are Dr. Dre and Snoop gonna bring out the Tupac hologram again during the Super Bowl halftime show? I would rather Maroon 5 play the Super Bowl again than deal with the Tupac hologram again.

I’m looking at the cover of Tupac’s first posthumous album. The Makaveli record. Called The Don Killuminati: The 7 Day Theory. Also from 1996. All Eyez on Me came out the day before Valentine’s Day in 1996. Tupac was shot four times in a drive-by shooting in Las Vegas on September 7, 1996. He died of his injuries a week later on September 14. The Don Killuminati record, which of course also debuted at no. 1, was out two months later, in early November, in plenty of time for holiday shopping. In terms of our public mourning, It feels insufficient to say the wound was still fresh. The wound was all there was. The only thing that seemed to soothe us was Tupac’s voice.

The cover of this Makaveli record is a painting that depicts Tupac Shakur as a crucified Jesus Christ. Below the cross it says, “In no way is this portrait an expression of disrespect for Jesus Christ,” signed “Makaveli.” I can’t imagine that disclaimer mollified the PMRC enthusiasts it intended to mollify. But this cover still exists in polite society, so I guess maybe it worked. The PARENTAL ADVISORY logo on this cover is pretty much dead center, covering the crucified Tupac’s private parts. It is the PARENTAL ADVISORY logo in its final, definitively contemptuous form. This album cover would be tremendously funny if not for literally every other aspect of this situation.

Crack magazine interviewed the guy who painted the cover of the Makaveli record, a guy named Ronald “Riskie” Brent, who said, “Being in the studio with Tupac, he would speak a lot about feeling like he was being crucified by the media and being blamed for things that he didn’t have any control over. The concept was all his, with the different cities on the cross showing he was the most hated wherever he would go. His crucifixion was supposed to be a statement about race and what it felt like to be young, rich, and Black in America.” Riskie also says, “The 7 Day Theory was originally going to be this underground album; Pac predicted the rise of mixtapes and was only going to sell it at the mom-and-pop stores. It only turned into a commercial album after he died.”

Finally, addressing the rumors that Tupac faked his own death, Riskie said, “If Pac was still alive, he couldn’t have kept quiet all these years!”

I take a perverse sort of comfort in the fact that unless you grew up hard in very specific pockets of New York City in the ’70s, or studied poetry and theater at the Baltimore School for the Arts in the mid-’80s, or haunted the nascent rap scene in Marin City in Northern California in the late ’80s—if none of that applied to you, the first time you heard Tupac Shakur’s voice was probably on a Digital Underground song.

I just rewatched the video for “Same Song,” from 1990, by Oakland legends the Digital Underground—RIP, Shock G, a.k.a. Humpty Hump—and this video’s probably gonna be the highlight of my day. Just an enormous heartwarming silliness to this video, even though it features copious amounts of footage from Dan Akroyd’s quite poorly reviewed 1981 horror comedy Nothing but Trouble, also starring Chevy Chase, John Candy, and Demi Moore. Forget all those other people. Concentrate on a young, unknown, exuberant Tupac Shakur as he raps about clowning around while being playfully carried around like a king. Functionally the first four words of his unprecedented blockbuster rap career are Now I clown around. The Tupac story gets so dark, so fast, that I am so heartened by the fact that at least he got his first big musical break with a group as sublimely ridiculous as the Digital Underground.

Get some fame, people change, wanna live their life high / Same song, can’t go wrong, if I play the nice guy. Yeah, we’ll see. Lesane Parish Crooks was born in Harlem, New York City, in 1971, and renamed Tupac Amaru Shakur a year later. Tupac Shakur was the name of an Incan revolutionary who led a failed revolt against the Spanish occupation of Peru in the late 18th century. The 20th century Tupac’s mother, Afeni Shakur, was a legendary figure in the Black Panthers who’d spent most of her pregnancy with Tupac in jail and representing herself in court as part of the Panther 21, a group accused of plotting various bombings and other attacks around New York City. That group was acquitted a month and three days before Tupac was born. Afeni has said, “I had to get a court order to get an egg to eat every day. I had to get a court order to get a glass of milk every day. I lost weight, but he gained weight.” Tupac’s father, Billy Garland, who was not a factor in his son’s life for the first 20 years or so and would not inspire any of Tupac’s goofier songs, was an active member of the Black Panthers as well.

That grounding in radical Black nationalism is not incidental, is not trivia. It informed, from the moment of his birth, everything Tupac thought and said and did. This was his lineage. This was his destiny. Tupac once said, of his mother, “She always raised me to think I was the Black Prince of the revolution.” Indeed, when Tupac was 10 years old, a pastor at the House of the Lord Church in Brooklyn asked him what he wanted to be when he grew up, and Tupac said, “A revolutionary.” He wasn’t joking and nobody thought he was joking. The pastor told that story at Tupac’s funeral.

Most of that is according to Rebel for the Hell of It: The Life of Tupac Shakur, a 1997 biography written by Armond White. The first Tupac biography, I believe. Yes, that Armond White, the incendiary, troll-adjacent film critic—he called the Pixar movie WALL-E “nihilistic,” he really loved that Adam Sandler movie Jack and Jill. He ain’t boring. Armond’s book does a great job of stressing Tupac’s musical and cultural lineage, the daunting and baffling jumble of it … the more politically provocative end of Motown, Gil Scott Heron, the Lost Poets, LL Cool J, Public Enemy, Morrissey, Lou Reed, Stephen Sondheim, Hamlet. The Shakespeare play, Hamlet. It’s a lot. It’s great. It all matters. Tupac’s mother moved the family to Baltimore in the early ’80s, and Tupac thrived, studying theater and so forth at the Baltimore School for the Arts, and it broke his heart to leave when his mother moved the family to Northern California in the mid-’80s. Afeni struggled with drug addiction, and struggled with a rebellious and unmoored teenage Tupac, who found a new calling as a rapper. At first he called himself MC New York. He hooked up with a group called the One Nation MCs. He found his way to the Digital Underground, who first took him in as a backup dancer. But rap stardom, solo rap stardom was his destiny.


To hear the full episode click here, and be sure to follow on Spotify and check back every Wednesday for new episodes on the most important songs of the decade. This excerpt has been lightly edited for clarity and length.