The thing that’s always made Dave Chappelle so charismatic has been his intriguing ability to go away and reflect, and then bring his learnings from that place of quiet into his work. A quality that we’ve seen in some of the most celebrated artists over time, and one that Chappelle seemed to have mastered in his last few Netflix specials. But on The Closer—apparently his final special for the platform—the veteran comedian seems to have abandoned introspection and growth for boomer intransigence. So much so that it almost feels like a relief that there isn’t another special in the pipeline. Perhaps a long break is what is sorely required. 

Dave Chappelle, who always managed to rise above, whose engagement with “phobias” and “isms” seemed always to be obvious—and usually brilliant—satire, now seems all too human. On The Closer, he displays all the sad weaknesses of mere mortals: insecurity, stubbornness, and an inability to see one’s own flaws and mistakes.  

(Spoilers Ahead)

It’s not that Chappelle has forgotten how to be funny or incisive. There are some classic Chappelle bits here about Israel, COVID-19 and yes, even feminism. But the bulk of this special attempts to deal with just one topic: the comedian’s alleged transphobia. Chappelle is so outraged by the suggestion that he spends much of his stage time tying himself up in knots, alternating between claiming that he can’t be transphobic because he’s black and understands suffering, and essentially declaring that when it comes to oppression, race trumps all.  

Here’s a pretty damning fact. By June, 2021 was already considered the worst year in history for trans Americans, with most victims of transphobic murders being black or Latina women. Black trans women are one of the most marginalised and vulnerable communities in the United States (and the situation for trans people of colour elsewhere is equally grim). So it’s hard to take Chappelle seriously when he says he can’t “punch down” on trans people because, well, he’s black. 

Equating trans-ness with whiteness, and therefore privilege, is in fact as wilfully problematic as the early feminists he vilifies in the special. Chappelle doesn’t see the irony of invoking Sojourner Truth’s fiery ‘Ain’t I A Woman’ speech—which called out the exclusionary and inegalitarian nature of early white feminism—all while making his own case for a hierarchy of causes that puts his own cause on top. 

Intersectionality works both ways—when it benefits your community, but also when it may benefit those you do not count within your community. If Chappelle were inclined to listen, there’s a whole group of people out there whose turn it is now to say ‘ain’t I a woman?’

That’s the sort of insightful punchline that could have been moulded into a classic Chappelle bit, if not for the fact that his very public battle with transphobia has become a blind spot, quite an embarrassment for an artist whose self-awareness has been one of his biggest strengths. 

The saddest thing is one gets the feeling that he gets it, but it’s almost as if having backed himself into this corner, he is now forced to defend it.

Beneath the wild-eyed imagination and scathing wit, Chappelle’s work has usually engaged in a pursuit of universal truths and justice. He’s always been fighting for the underdog. But by taking on the trans community as nemesis, he now sides with those who in almost all other matters, hold views diametrically opposite to his. What the trans community is facing especially in America, with Trump-era Republican legislation pitted strongly against them, is something one would expect Chappelle, self-declared lover of all kinds of freedoms, to be dead against.

The most moving part of the special, anchored by the story of a trans friend he had called Daphne, who laughed at all his trans jokes, also showcases how Chappelle is getting tripped up by his own biases, clouding the intellectual clarity that made him such a sharp comedian. It’s the only way to explain how he doesn’t see the obvious, and damning, alternative interpretation of this story. Imagine a white comedian getting up on stage to talk about his one black friend who laughed at all his n-word jokes. Imagine him saying that this friend eventually killed themselves because of social media pressure, which the comedian then blames on this friend speaking up to defend him for “racism”. Then imagine how Dave Chappelle would rip that white comedian apart. 

Yes, Chapelle has opened a trust fund for his latefriend’s child and that’s commendable, but what portion of his own guilt in this story has he dealt with? Throughout the telling of this story, you keep hoping he will rise up like the mythical phoenix, and use this moment to elevate himself: to admit, the way he has about so much in the past, that maybe he was wrong. That maybe all those years ago that one show that started this, that one article that was written that to this day is quoted against him, is something he regrets. If nothing else, it’s something he has decided to reflect on. 

You wish that he might use his incredible creative genius to frame his complex and nuanced feelings about this subject as a frank discussion with himself, as he has with Bill Cosby and OJ Simpson in past specials. But that moment never comes. The saddest thing is one gets the feeling that he gets it, but it’s almost as if having backed himself into this corner, he is now forced to defend it. The result is a meandering series of confused jokes where he keeps announcing his transphobia, then explaining how he isn’t in fact at all transphobic, telling stories to prove the same, ending by saying something highly transphobic, then insisting black people have it so hard, something no one ever argued against, and that grates ironically like an #alllives post. 

Chappelle keeps announcing throughout the special that this time, he’s going to go “all the way”. But when the end comes, with an unintentionally self-parodying insistence that empathy works both ways, you’re left with the feeling that he hasn’t gone anywhere. That he is, in fact, a little bit stuck.