Two decades after his death on September 13, 1996, Tupac Shakur endures as one of hip-hop’s most iconic figures and its most powerful enigma. His life was a tapestry of often contradictory images: the concerned young father cradling his son in the video for “Keep Ya Head Up”; the angry rapper spitting at cameras as they swirled around his 1994 trial for sexual assault; the artist who animatedly, yet eloquently, pushed back at Ed Gordon’s questions during a memorable BET interview; and the man who seemed to predict his own demise when the “I Ain’t Mad at Cha” video, released weeks after his death, depicted him as an angel in heaven.
Related: Watch Trailer for ‘All Eyez on Me’ Tupac Shakur Biopic
Although he is no longer with us, the myth of 2Pac the thug angel remains. No other artist better illuminates hip-hop’s fault lines between regional pride and mainstream success, and the struggle to transcend and elevate beyond humble origins while honoring the streets that raised you. His wayward, conflicting expressions of pride, militancy and gangster-ism resonates in a world when black men and women celebrate their heritage and collectively organize against a racist America, yet are also cautious to protect themselves from each other.
Fans – particularly East Coast rap listeners who, after all these years, still harbor a grudge against him – will continue to debate whether 2Pac’s albums can measure up to Nas’ Illmatic, the Notorious B.I.G.’s Ready to Die, or Jay Z’s Reasonable Doubt. But no one can deny the way he transformed hip-hop into his singularly muscular, tattooed, bald-headed, bandana-clad image. Here are some of the ways 2Pac changed hip-hop – and, by extension, pop culture – forever.
1. Shakur’s appearance in Juice as Bishop, the troubled high school teen who fashions himself into a cold-hearted killer, is the first great dramatic performance by a rapper in a movie.
Yes, Ice Cube launched his acting career with his understated depiction of the Compton crack dealer Doughboy in Boyz N Tha Hood, which preceded Pac by a year. Months after Juice debuted in theaters in January of 1992, Ice-T would become a movie star in New Jack City. But Shakur, who studied acting while attending high school in Atlanta, commanded the screen with an effectiveness that no rapper-turned-moonlighting-actor had managed before, and few have done since. While he didn’t realize the promise of that early breakout role, he managed a few more solid acting performances before his death, including an overheated reprisal of his Bishop template in the basketball drama Above the Rim, and a nice turn as a heroin-addicted jazz musician in the underrated indie flick Gridlock’d.
2. He’s the man who single-handedly transformed a common epithet for a criminal into a source of masculine strength.
After recording two albums – the muddled 2Pacalypse Now and the slightly improved Strictly 4 My N.I.G.G.A.Z. – Shakur unveiled his crew T.H.U.G. L.I.F.E., an acronym for The Hate U Gave Little Infants Fucks Everybody. At the time, it seemed like an unnecessary variation on the “gangster” trope that dominated West Coast rap at the time. However, his reimagining of a word that the Oxford Dictionary defines as “a violent person, especially a criminal” into an positive attribute resonated. 2Pac’s vision redefined the word “thug” into a man who triumphs over systemic and societal obstacles. By the end of 1994, Cleveland quintet B.O.N.E. Enterprises had renamed themselves Bone Thugs-N-Harmony; the word has been since been adopted by Young Thug, Slim Thug and too many others to mention.
3. Shakur’s New York trial for sexual assault was arguably the first rap celebrity court case.
He had already tangled with the legal system on numerous occasions, particularly when he shot two off-duty police officers in 1993. But the 1994 cemented his reputation as a livewire with a flair for drama. The press hungrily publicized his every move, like the aforementioned spitting episode and, more tragically, his appearance at his sentencing date in a wheelchair after he infamously sustained five gunshots from unknown assailants at Quad Studios. Countless rappers have weathered the legal system since, but none with as much tumultuousness.
4. Before Shakur reported to prison for his sexual assault conviction, he completed the first rap “pre-prison” album.
Released in May while Shakur was incarcerated, Me Against the World is arguably his most concise and moving work. It found him making peace with his mother, Afeni Shakur on “Dear Mama,” and ruminating over his mess of a life on “Lord Knows.” “It ain’t easy being me/Will I see the penitentiary, or will I stay free?” he asks on “It Ain’t Easy.” There are also notes of joy like “Old School,” an exuberantly goofy tribute to his rap heroes, and “Outlaw,” where he flashes ill-advised anger at the woman who brought charges against him. 2Pac’s mixture of remorse, regret, suicidal despondency and life-affirming hope has echoed in “pre-prison” albums like Lil Kim’s Naked Truth, T.I.’s Paper Trail, and C-Murder’s The Truest Shit I Ever Said.
5. Shakur signed with the hottest and most dangerous record label in America, Death Row, and dropped the first hip-hop double CD.
1996’s All Eyez on Me teems with “gangsta party” hits, high-wattage collaborations, and even samples – contrary to popular belief, G-funk producers sampled nearly as often as their East Coast counterparts. It’s hard to describe an album that’s certified Diamond for selling over 10 million copies as “underrated.” But All Eyez on Me‘s reputation is closely tied to Pac’s image at the time as a shit-starter, leading his growing critics to downplay exemplary tracks like “Ambitionz Az a Ridah” and “Heartz of Men.” Nevertheless, its two-disc sprawl inspired a brief wave of double-album opuses, including Biggie’s Life After Death, Wu-Tang Clan’s Wu-Tang Forever, E-40’s The Element of Surprise and, more recently, Jay Z’s Blueprint 2: The Gift and the Curse.
6. Shakur is the first dead rapper that made people think he’s still alive.
No other rapper has generated a legend as profound as The Don Killuminati: The Seven Day Theory, the 1996 album that fueled widespread belief that he had somehow survived the Las Vegas shooting. There was speculation that Pac called himself Makaveli to evade his antagonists, much as the political theorist Niccolo Machiavelli had claimed to do in The Prince five centuries earlier. “The Seven Day Theory” is modeled on Machiavelli’s claim that he faked death for seven days; Shakur was pronounced dead six days after being shot. As an argument that Shakur is chilling on an island somewhere, it’s suspect. As an incredible piece of myth-making, it has no equal in the genre.
7. Beginning in November 1997 with R U Still Down? (Remember Me), Shakur becomes the first rapper to have his estate mine-stripped for new product.
This practice dates back to the days of Patsy Cline, John Coltrane and Jimi Hendrix, but had no real equal in hip-hop. The “Tupac effect” is subsequently used for any rap artist of note who meets an untimely demise, including the Notorious B.I.G. (Born Again), Big Pun (Endangered Species), Big L (The Big Picture), and J Dilla (Jay Stay Paid).
8. He recorded a staggering amount of material.
Before Lil Wayne flooded the Internet with his Drought and Dedication mixtapes, and Lil B bragged “you’re not a real rapper until you make a thousand songs,” hundreds of tracks from Shakur’s Death Row sessions appeared on compact disc. The bootlegs not only intensified talk that he was somehow still alive, but led to accusations that Suge Knight, then in prison and battling Afeni Shakur over control to Tupac’s work, was responsible for the leaks. “13 bootleg albums of his unreleased material have hit the streets. Is Death Row responsible?” asked Rap Pages, which dedicated a September 1998 cover to “The Raping of Tupac.” Regardless of the source, Shakur’s posthumous deluge set a precedent that everyone from Weezy to Gucci Mane follows to this day: Stay in the studio, and feed the streets until it bursts.