Dave Chappelle: From Un-Famous to Infamous

“I hope this shit don’t make me famous. I don’t want to be famous famous,” Dave Chappelle stated at the end of his first TV special, a 1998 episode of HBO Comedy Half Hour. “I want people to like me for who I am.” Five years later, Chappelle would be famous famous, becoming one of the biggest comedians ever with the success of Chappelle Show. A decade later, Chappelle would be largely out of the public eye, making the occasional appearance at clubs, sometimes going for hours on end. Two decades after that first half hour, Chappelle makes his return to stand-up specials with The Age of Spin and Deep in the Heart of Texas—both premiering on Netflix the same day, with a third special on its way. With Chappelle’s specials, we can see what fame has gotten him, how he bucks against the fame and how popularity informs his stand-up.

In the aforementioned HBO Comedy Half Hour, Chappelle has a two-sided view of fame. Early on, you can see Chappelle is hungry for recognition, yet is already afraid of how fame will change him. “Famous dudes will never know why people like them,” Chappelle says near the end of his set. Throughout Chappelle’s sets, he seems to lure in his audience with over-the-top stories and tightly executed jokes at the beginning, then transitions into his true fears and uncertainties. For example, this first half hour begins with some of Chappelle’s favorite topics—police, drugs, strippers, race—then gets into how he will act towards people if he one day becomes famous.

Two years later, Chappelle essentially confirms his future success with Killin’ Them Softly, where he’s refined his storytelling to perfection. The first half of his breakthrough special is the best stretch of comedy Chappelle has possibly ever done. Whether he’s telling stories about talking to the cops while high, or babies selling weed on the corner, Chappelle always follows up every joke with equally great buttons, the tiniest additions that push the jokes into pure genius. Every time Chappelle says “let’s sprinkle some crack on him,” he’s building his joke to a breaking point, improving the line exponentially every single time he drops it. The second half meanders, but occasionally still hits on some of the brilliance of the first half, especially when he questions whether or not we will have a black president one day. As with his discussions of his future popularity, it’s almost as if Chappelle can see into the near future with his stand-up.

With Chappelle’s last special, 2004’s For What It’s Worth, one can already see the pressure weighing down on Chappelle after the gargantuan success of his TV show. Filmed after he had wrapped Chappelle Show’s second season, For What It’s Worth comes off as far more freeform than his previous specials. Some of his jokes on police are only slight deviations from what we’ve heard from him before, and considering his whip-smart takes on race from Chappelle Show, For What It’s Worth almost comes off hacky. His impressions of Native Americans and Asians is the first time Chappelle becomes borderline cringe-worthy.

Yet again, it’s that second half that brings the true Chappelle to light, as he states “being a celebrity is the worst,” and takes on the public’s worshipping of television. By this point, Chappelle had become the level of famous that he feared he would become only six years earlier. Chappelle brings up constant media attention of the O.J. Simpson case (a topic Chappelle will discuss in The Age of Spin), and the potential crimes of R. Kelly and Michael Jackson. It’s as if Chappelle has somewhat of a chip on his shoulder, and questions the focus we put on celebrity culture. In hindsight, it’s hard not to look at For What It’s Worth as Chappelle trying hard to reckon with the $50 million payday Comedy Central was throwing his way and how to move forward with his fame.

But possibly the best example of who Chappelle probably is comes from the Michel Gondry-directed Dave Chappelle’s Block Party. Apropos of nothing, in the summer of 2004, Chappelle decides to throw a massive block party in Brooklyn, a concert that will bring together such acts as a young Kanye West, The Roots, Common and a reunited The Fugees. Rather than coming off as a gimmick, Block Party feels simply like Chappelle trying to bring joy to the world in a way that having an exorbitant amount of money allows him.

Watching these great musicians come together is wonderful as it is, but Block Party is truly heartwarming and joyous when Chappelle simply goes around his current hometown in Ohio and invites random people to the party that he’s throwing over 600 miles away. Nowhere is that joy more palpable than when Chappelle invites the Central State University Marching Band to perform at his show. The surprise announcement leaves the band hardly able to contain their excitement, jumping and hugging at Chappelle. Throughout the film, we catch up with the members, playing “Jesus Walks” for West, or being lectured by Wyclef Jean offstage. It’s the type of experience that these young men and women would likely never get to experience in rural Ohio, but being famous famous allows Chappelle the ability to give these people a moment in their lives that they’ll never forget.

This looks to be the type of fame Chappelle now wants. He doesn’t want to be known as Rick James or Lil Jon, as seen from him murdering his characters earlier this year on SNL. He’d rather be the man who can bring joy while also making you think. From that first HBO half hour, it’s clear he revels in making people laugh, and revolts against the idea of fame. At the end of Block Party, Chappelle states that the show he has just put on has provided the “best single day of my career,” and you can feel it in his reactions and demeanor. As Chappelle once said on Inside the Actor’s Studio, “you can’t get un-famous. You can get infamous, but you can’t get un-famous.” Chappelle can’t go back from the future he once saw from himself, he can only do his best for a positive future.

At this point, it seems as though Chappelle would rather give people a true experience that they won’t forget. After the frustration over being a celebrity in For What It’s Worth, Block Party gave Chappelle the freedom to control his own legacy. He knows that performing at the Comedy Cellar like he did earlier this year with Chris Rock, Amy Schumer, Jerry Seinfeld and Aziz Ansari will be an unforgettable moment for everyone in attendance. Or that hosting SNL with A Tribe Called Quest as musical quest will be an unmissable television event. In an incredibly short time, Chappelle went from great comedian into icon, and in a similar way, Chappelle seems ready to become a maker of memories, creating situations that won’t soon be forgotten. With Chappelle coming back with The Age of Spin and Deep in the Heart of Texas, it’s not certain where this phase of his career will take him, but it looks as if Chappelle is ready to surprise his audience again.

Ross Bonaime is a D.C.-based freelance writer and regular contributor to Paste. You can find more of his writing at RossBonaime.com and follow him on Twitter.