Dave Chappelle's new comedy special The Closer proves he just doesn't get it. Which is frustrating because his thinking and his message are usually so on point.
Chappelle is a comedian who can articulate societal issues in a way that's both profound and profoundly funny. He takes risks with his comedy, provokes and trolls in a way that, at his best, sees you gasping for air while imparting topical wisdom to ruminate on long after he's dropped the mic and the credits have rolled.
Chappelle doesn't write comedy just to make you laugh. He crafts his jokes to make you think about the world and society you live in.
Although not without controversy, his run of comedy specials that began in 2017 have been a masterclass in comedy by a comedian who has a stronger claim that most to the title of the GOAT, or Greatest of All Time.
But even the great boxing legend Muhammad Ali took the odd loss. And Chappelle's final special in his eye-wateringly lucrative deal with Netflix really is a self-inflicted KO.
The Closer sees Chappelle come out swinging. He opens recounting his experience getting Covid ("Turns out, I didn't get sick at all") and somehow segues into a tall tale about getting molested by a preacher as a boy.
"Oh, don't feel bad for me," he admonishes, before enthusiastically grinning. "I liked it."
"It's gonna get worse than that," he warns, smiling devilishly. "Hang in there."
These opening rounds are like a champion fighter working the jab, testing his opponent and softening them up for what's to come.
"I have an objective tonight," he says, seriously. "This body of work I've done on Netflix I'm going to complete."
Then he says, "I'd like to start by addressing the LBGTQ community directly," while his audience erupts in claps and cheers.
It's hard to know if they misheard and are showing support for the marginalised community or if they're applauding his purposeful jumbling up of the representational letters which, I guess, is supposed to be funny.
The next 45minutes consists only of Chappelle punching back - not down, he insists endlessly - at the communities that've been vocally displeased by the many jokes and barbs he's fired at their expense over the years. Primarily women and LGBTQ.
That they're unhappy is fair enough. No one likes being the butt of someone else's jokes. Just look at how worked up people get about being called "boomer" or "woke". It's all fun and jokes until someone's laughing and pointing at you.
However, Chappelle's ire here is mainly directed at the trans community after a friend warned him, "they're after you".
"One they," he ponders with mock concern, "Or many theys?".
That's a very good pronoun gag. Chappelle's smart and funny and peppers similarly terrific bits of wordplay, clearly written as wind-ups and delivered with a cheeky grin, throughout.
"What I think the feminist movement needs, to be very successful, is a male leader," or, "What would make these b*****s think I hate women?"
His gags are purposefully provocative and delivered with a knowing irony that lets you know he knows he's out of line and is just joking around. You can take a joke can't you?
But is that one joke or many jokes? Because where it falls apart is that he can't let any of it go. He'll do a bit on gays or lesbians or trans or women and then do it again. And again. All the while claiming offence that people are offended by all the wilfully offensive jokes he's told.
To end the show and prove he doesn't hate trans people he tells a story about befriending a trans comedian named Daphne Dorman. This is a little like saying you're not racist because you have a friend who's a person of colour right before you spout some racist stuff.
He then tells us that Dorman died by suicide a few weeks after being mentioned in his last comedy special. His shout-out led to "her tribe", the trans community, piling onto her on social media. He talks of losing his friend, how that felt and says he's started a trust fund for her daughter.
It shows a humanity otherwise buried underneath his gleeful trolling and feels like it's heading to the promised land of poignancy and wisdom that he so often leads us to.
And then he undoes it all with an admittedly quite clever but entirely undermining and quite awful punch line.
"He was a hell of a woman," Chapelle says, entirely too satisfied. It proves he just doesn't get it. Which at this point can only be considered a deliberate choice.
Then, tired, he says, "LBGTQ... LMNOP... QYZ it's over," still clearly unable to resist getting in a final dig. "I am not telling another joke about you until we are both sure that we are laughing together."
It's the GOAT of empty threats and, sadly, the only wise thing this incredibly smart comic says during the whole damn show.