It’s been a decade now since Comedy Central signed off on the final editions of “Chappelle's Show” behind the back of its host and creator. The three “lost episodes” glued together the completed skits from the abandoned third season, revealing the tense working environment that caused a visibly jaded Dave Chappelle to abscond to the relative anonymity of South Africa. Looking back, the desertion wasn’t so shocking: The comedian had been operating on a level so high it couldn’t possibly last.

Harnessing the savage spirit of his stand-up, “Chappelle's Show” ridiculed celebrities, crowbarred open racial taboos, and exposed the cultural woes plaguing America. The series debuted with Chappelle playing a blind white supremacist who doesn’t know he’s black. Season two finished with Black Bush, a skit that butchered George W’s presidency. Every episode in between was a shotgun slug to the chest, but not so loud that you couldn’t hear the laughter.

Dave’s legacy is undeniable—not just in comedy, but also in music. “Chappelle's Show” moved to a hip-hop beat. Rappers were the co-stars, and live music was stitched into the show’s ethos. The star would walk out to the sound of socially-engaged rap duo Dead Prez; it’s not hard to imagine that his love of politically-charged, conscious rap fueled his most daring sketches.

For too long Chappelle lived almost completely off the grid, like it took a lot of years for him to rest up and recover after that all-too-brief rush of genius. A 2014 run of Radio City Music Hall shows saw him back under the bright lights—and sharing the stage, again, with Kanye West, Nas, Erykah Badu, Janelle Monáe, Busta Rhymes, DJ Premier, and the Roots. It was further proof of an influence that continues to resonate across hip-hop and beyond. Here’s why.

A Champion of Talent

“Chappelle’s Show” episodes typically were punctuated with a live musical performance, with guests seemingly snatched out of the host’s own CD rack. The biggest-selling rappers of the day included Eminem, Nelly, and Ja Rule, but Chappelle had more distinctive taste than that. Instead he put up Killer Mike right before his first album, 2003’s Monster, dropped. In addition to numerous heroes of the hip-hop underground, neo-soul was also highlighted, via guests like Erykah Badu and Anthony Hamilton. Kanye West performed twice in the weeks after The College Dropout came out. It was a step on his road to superstar status, while forever crystallizing the beatmaker-with-a-backpack guise he’d later shake off.

Inventive Live Performances

Not only were these performances often tastemaking (particularly for a mainstream series), they also routinely echoed the show’s distinct guerrilla aesthetic. There wasn’t exactly a boilerplate on-stage set-up for musical guests, with the visuals regularly popping as brightly as any other skit. Episode one saw Mos Def in Dave’s passenger seat. Rapping to a taped beat as the host drove around, it predicted James Cordon’s bizarrely popular “Carpool Karaoke.” Kanye and Common performed “The Food” in a kitchen, a version that would be included on the latter’s album Be. De La Soul rapped on their tour bus, while Talib Kweli gave an outdoor rendition of “Get By” with the Brooklyn Bridge looming in the background. No two performances were alike, and many weren’t quite like anything seen on TV before or since.

Rappers Making Fun of Themselves

Lots of rappers have jokes, but in an industry where grit is often valued above all, not all of them are exactly into self-ridicule. “Chappelle’s Show” allowed rappers who didn’t typically engage in such mockery to cut loose in a way that made fun of typical hip-hop tropes. Lil Jon took part in Chappelle’s none-too-flattering depiction by starring in a phone call with “himself.” Ice-T dropped by the Playa Haters’ Ball, ribbing on the Blaxploitation fashion cues he incorporated from his superfly ’70s heroes. RZA and GZA poked fun at rap entrepreneurism with Wu-Tang Financial, while Dame Dash hawked his own sanitary towel brand Roc-A-Pads. Chappelle gave these guys the space to scorch their own personas for kicks, and they used it.

Mocking His Generation

Music wasn’t just a passion of Chappelle’s—the industry inspired some of his most cutting material, with Dave finding comedy in the darkest corners. He jolted audiences with his on-stage takes on the 2005 Michael Jackson trial, putting out a conspiracy theory that the litigation was just to distract the American public from what was going on in Iraq. On the lighter end of things, he targeted Puff Daddy by portraying him as an over-pampered prima donna, and poked fun at the oceans of posthumous Tupac tracks. R. Kelly’s career inexplicably continues to survive the lurid allegations that hang over him, but during the first wave of claims, Chappelle was there, flipping “Ignition” into a different kind of remix: an urolagnia anthem. Dave wasn’t just relentless, he was necessary.

Rick James and Prince

Charlie Murphy’s “True Hollywood Stories” was the fuel that powered “Chappelle's Show” from beloved cult oddity to cultural phenom. Taking Eddie Murphy’s brother’s surreal real-life tales as his inspiration, Dave’s caricatures of Rick James and Prince have become so recognizable, they’ve been absorbed into the artists’ own iconographies. His “I’m Rick James, bitch” catchphrase is as deeply embedded in the pop lexicon as the funky showman’s “Super Freak.” Prince, we learned, could shoot threes and flip pancakes almost as well as he shred the guitar. The Purple One even gave Chappelle’s performance his approval by placing a photograph of the sketch on the cover of his 2013 single “Breakfast Can Wait.”

Dave on the Mic

Music flowed through the veins of “Chappelle's Show,” so it was inevitable that its host would jump on the mic every now and then. He may have assembled Questlove and John Mayer for one of his most indelible sketches, on which instruments get different cultures dancing, but he couldn’t let the pair leave without putting together an impromptu supergroup to help him perform the themes to “Diff’rent Strokes” and “The Jeffersons.” Dave couldn’t sing or rap to a recording standard, but he brought charisma on the mic. He teamed up with Snoop Dogg in the guise of tweaked-out crackhead Tyrone Biggims, and cut a commercial for mock track “Turn My Headphones Up,” which has made all orders barked from rapper to the boards since sound positively ridiculous.

Rock the Block

Dave Chappelle’s Block Party, the 2005 documentary that charts the organization and staging of an all-star concert at a Brooklyn intersection, was dedicated to the recently-departed J Dilla. Fittingly, the movie leans on the soulful grooves and offbeat rhythms of the producer’s hip-hop collective, the Soulquarians. With Questlove serving as arranger, the live music is raw and vibrant. Mos Def, Common, Erykah Badu, and Talib Kweli are among the performers. Headlining after seven years dormant, though, were the Fugees, coming together for a show that would spark several years of activity. “This is the concert I always wanted to see,” Chappelle says. Block Party solidified its star’s musical world.