Halfway through The Closer, his latest special on Netflix and his last for a while, Dave Chappelle recounts the story of a fan walking up to him on the street and saying: “Careful Dave, they after you!”.
A shocked but curious Chappelle responds with: “One they, or many theys?”
It is true; in his long and influential career, the 48-year-old has pissed off many a community, including some of his own when he said he would “give Trump a chance” in his Saturday Night Live monologue in 2016.
But the one group that takes the most offence is “the alphabet people”. The LGBTQIA+ gang, that is. Ever since he returned to the mainstream after quitting the pioneering sketch comedy series Chappelle's Show in 2006, and started putting together stand-up specials for streaming giant Netflix, an inordinate amount of his jokes have focused on the LGBTQIA+ community, especially the transgenders.
About 15 years ago, Chappelle, in his own words, walked away from $50 million because he thought his cutting-edge material was garnering the wrong laughter; a crew member laughed at him, and not with him, which prompted him to wrap up and leave.
He took a stand for something he believed in, and that cost him the peak of his career. It is strange then, that when he returned, he fixated on a group that could have been an ally for his cause of racial justice.
But, somehow, he made it a competition. He said he was “jealous” of how much the transgender community had achieved in such a short time. Referring to an earlier Netflix special, he says in The Closer: “You never asked yourself why it was easier for Bruce Jenner to change his gender than it was for Cassius Clay to change his name?”
At the end of the day, though, these are jokes made in a specific setting, within a specific context. Taken in isolation, each of Chappelle's statements could spark outrage. Having said that, even when immersed in the show, and setting aside “impropriety”, the trans jokes are less funnier than the others.
His previous special, aptly titled Sticks and Stones, had gotten the most stick from the transgender community, as well as from progressives who felt he was defending Michael Jackson (he cast doubt on those who accused the musician of molesting them as children). It is telling then, that his latest outing has no mention of Jackson, but a lot of minutes on his trans-gressions.
Craft wise, though, he is still a master. He carefully builds up to every uncomfortable joke. It is like he is filling up a balloon in full view of the audience, so that they know to cover their ears when it bursts, and they are, in most cases, not surprised by the pop.
He is at his ferocious best when talking about race relations in the Trump era; the 2020 YouTube clip called 8:46, about the George Floyd murder, was especially raw and moving.
After Sticks and Stones won three Emmys in 2020, Chappelle brutally proclaimed: “I hope all you critics learn from this. This is a teachable moment. Shut the fu*k up forever.”
Perhaps buoyed by that recognition, Chappelle forges on, ending The Closer by saying he was done talking about transgenders. He claims that, if the audience had listened clearly to all the transgender jokes across specials, it had always been about the whites.
It is, of course, the artist’s prerogative to talk about whatever he wants. And stand-up comedy is not activism. But there is no denying that his trans-arrow is less piercing than the others in his quiver. And it often misses the mark, too.