efore he took the stage at Radio City Music Hall last June, nine times to nine sold out audiences. Before his decade in seclusion. Before he walked away from a $50 million contract and onto a plane bound for South Africa. Before his two season show on Comedy Central elevated him to a demigod in social satire and racial comedy. Before Half Baked, Robin Hood: Men In Tights and performances in the Washington Square Park fountain, Dave Chappelle left high school after the bell rang and got onstage at a Tuesday night open mic. He was 14. He killed it.

Months before he got onstage that first time, his mother bought him a TIME magazine with Bill Cosby on the cover. Years later, in an interview on Inside the Actors Studio with James Lipton — Lipton would eventually introduce him at Radio City Music Hall — Chappelle said he put the magazine down and “was so excited [he] told [his] family, ‘I have an announcement to make, I’m gonna be a comedian.’” Not long afterward, with his mother and grandmother in tow, Chappelle took to the stage in Washington DC for his first performance.

Even as a 14-year-old, Chappelle’s subject matter — from a Jesse Jackson presidential campaign to Alf’s spaceship landing in a black neighborhood — was already toeing a line he would come to cross and recross for a generation, talking about race fearlessly and earnestly throughout his career. His material was extremely divisive, and, at a young age, he was booed off the stage at Apollo’s amateur night — a bombing he attributes to his on stage fearlessness. In the early 1990s, Charlie Barnett, a legend of racial comedy in Washington Square Park, acted as a mentor to Chappelle, helping him soften a crowd to uncomfortable material. Barnett would let Chappelle perform in front of his massive crowds lining the park’s fountain, teaching Chappelle how to work an unruly crowd and advancing his skillset for the national stage.

Chappelle became the youngest comedian to premiere on the HBO special Comic Relief VI

By dealing with race in an intelligent way, by bringing differences to light and having white and black and asian laugh together, not at one another, Chappelle succeeded. This balancing act, the impossibility of being both extremely offensive and extremely important to our nation’s social dialogue, came to define Chappelle’s Show, which he hosted and wrote alongside Neal Brennan. The show, which ran on Comedy Central from 2003 to 2005, featured a series of skits notorious for pushing the limits, including a particularly controversial clip about a white family with the last name of Niggar.

The show ran for two complete seasons — the first season being the best selling TV-to-DVD set ever produced — before Chappelle abruptly walked away in 2005 from a reported $50 million contract during the third season. With skits and characters suddenly being laughing at, rather than with, Chappelle said in an interview with Oprah that he felt socially irresponsible, and that he had lost control of how his work was being used and consumed. This apparently came to a head when Chappelle felt a white crew member’s laughs were too loud and too long while Chappelle performed a sketch in black face as a black pixie. The stress of potentially reinforcing stereotypes, rather than examining them, led him to take time off.

His demeanor has matured, and, for the worse, so have his jokes.

After his hiatus, which was so abrupt it had news media speculating everything from drug use to a conspiracy involving Oprah and Bill Cosby, Chappelle returned to the stage, dropping in unannounced at clubs in L.A. and New York before announcing his New York debut at Radio City Music Hall in June of 2014.


On the last night of Chappelle’s nine-day stint in New York this June, James Lipton’s face — the deadpan eyeglasses from Inside the Actors Studio — spread across a Jumbotron and told everyone to “Turn off [their] mother fucking cell phone.” This wasn’t just for laughs; crowd control is important for Chappelle, who brings a lot of baggage.

This baggage followed Chappelle to Hartford, CT last year, where he performed in front of a predominantly white crowd raised on Chappelle’s Show. Chappelle was heckled until he was forced to stop performing; he waited, sitting silently on stage, until the end of his set and then walked off to Kanye West’s New Slaves. The crowd was yelling at him in the way they had seen Chappelle scream during his show, loud and confidently shoving, “I’m Rick James, bitch!” into the American lexicon of the early 2000s.

In regards to the Hartford show, David Canton, a history and black culture professor at Connecticut College, told NPR, “They were probably looking for Dave Chappelle to talk about Ashy Larry, Rick James — all the skits that they grew up watching on the Comedy Central show. I think he wants to reinvent himself as a comedian, and move away from [Chappelle’s Show].”

Chappelle wasn’t back to reinvigorate old conversations, or even to climb back on top. He was back because he could fill Radio City Music Hall nine times, even when the cheapest ticket topped $90.

This June, onstage at Radio City Music Hall, Chappelle was distancing himself from the work he had done in 2003 and 2004 — the work that had fueled a national race conversation, a conversation Chappelle felt had ultimately gotten out of hand. Now he stood on stage in all black, chain smoking, as at ease as someone who had been performing in front of crowds his whole life and as disinterested as someone who had thrown it all away.

And he wanted to keep it thrown away. Chappelle wasn’t back to reinvigorate old conversations, or even to climb back on top. He was back because he could fill Radio City Music Hall nine times, even when the cheapest ticket topped $90. Chappelle even admitted as much, asking the crowd “Why am I back?” and answering for them, “Because private school is expensive.”

His demeanor has matured, and, for the worse, so have his jokes. Along with quips about Donald Sterling and Rob Ford, the type of material that echoes Killin’ Them Softly (2000) and For What It’s Worth (2004), were truths about adulthood. They were small, personal anecdotes that were funny, yet mostly unrelateable and petty. Instead of targeting his jokes at all blacks, all whites, all Koreans, Chappelle was now telling jokes about sending kids to private school or masturbating while his wife was away. The jokes weren’t bad — they just weren’t the kind of grand world views Chappelle had been funneling through a microphone in the early 2000s, flipping convention on its head through storytelling, like a 21st century Mark Twain.

Gone was the passion. Gone was the urgency. It was like a Kanye West song, ten years after New Slaves; West knows his name and a small amount of effort will make him another million or five. Social advocacy is a young man’s game, and Chappelle seemed tired and content with the part he played before leaving his show and escaping to South Africa.

But that’s okay. We gave Chappelle the national stage in 2003 and 2004 and then inadvertently drove him out of town in 2005. The torch he carried has been passed on, most recently to Louis CK, who deconstructs social convention via his standup and his hit show Louie. Progressing our society’s dialogue on race is not one comedian’s burden. It’s bigger than that: a sequence of men and women who take the microphone at just the right time, with just the right nuance and perspective. Chappelle’s time has passed, and he knows it. His work will always be legend, but now his focus is on comedy for comedy’s sake and, admittedly, paying tuition.