It goes without saying that Chappelle is a force. His decision to walk away from Comedy Central’s $50 million offer in advance of a third season of Chappelle’s Show is a watershed moment, particularly for Black creatives. His elusiveness that followed only heightened his legend and increased the anticipation and enthusiasm that audiences have for his appearances and specials.

Despite his stature and success, it seems like Chappelle is content to keep pushing the envelope, perhaps less for himself and what he sees as the sake of comedy. With his latest, The Closer, Chappelle picks up where 2019’s Sticks and Stones left off, this time focusing his time on stage almost entirely in discussion with and about the LGBTQ community - particularly trans men and women. In the aftermath of both specials, Chappelle has been accused of transphobia, though these claims do not seem to deter him. It’s clear that Chappelle knowingly acted as a provocateur throughout, warning the audience "It's gonna get worse than that," as it groaned with discomfort at his “Space Jews” joke.
Chappelle includes a poignant and human story about comedian Daphne Dorman, a trans woman who he befriended and mentored, who later would defend him after his Sticks & Stones, aired. Dorman took her own life soon after; and much has been said about whether or not Chappelle exploited her story to shield himself from critique. Or was Chapelle chastising a community that perhaps hurt one of their own because Dorman defended Chappelle..
Since its Oct. 5 release, Chappelle has been under fire. ““If this is what being canceled is like, I love it,” he said to an enthusiastic standing ovation at the Hollywood Bowl just days later. It is of note that the crowd was filled with fellow big-name entertainers, others who perhaps also tow the line to avoid being cancelled themselves, who similarly feel that their artistic expression has been put into jeopardy by an immediate feedback loop made possible by social media.
Outside of the ivory tower of celebrity, Netflix employees have planned a walkout in response to the company’s decision to defend its partnership with Chappelle.

The walkout organizer (who is trans) was also terminated on suspicion of leaking sensitive and proprietary details about Chappelle, including information about pay and performance metrics. These details were subsequently published in Bloomberg.
Netflix leadership has defended its relationship with the comedian based on its stance on “artistic expression,” with co-CEO Ted Sarandos claiming the “content doesn’t directly translate to real-world harm” in a leaked internal memo. Predictably, this statement was not well received by employees; Sarandos later admitted “screwing up” for the phrasing, but not necessarily for his opinion.
No doubt, Chappelle has turned off some audiences and so the question remains if his legend will weather the tide--can a man blow up his career twice and live to tell the tale? From the looks of it, the answer is “yes.” Netflix seems resolute in its decision to defend its relationship with the comedian, which seems almost novel in a time where corporations cleave to the sentiments of trending topic discourse. What’s unclear is whether Chappelle’s ability to remain standing is because of the heft of his own legend, or because he was successful in his role as a sacrificial lamb on the altar of comedy for his peers.