Watching Dave Chappelle has been an exercise in prolonged frustration in recent years. Arguably the greatest standup comedian alive, Chappelle has worked despairingly hard at destroying his legacy. His fixation with cancel culture would’ve been bad enough by itself. But in Sticks and Stones (2019) and The Closer (2021), Chappelle revealed an even more pernicious obsession—making juvenile, bigoted, genitalia-centered jokes about trans people. To see one of comedy’s sharpest, subtlest intellects behaving like a hopped-up 4chan goon was dispiriting, to say the least. It should be noted that when he stayed away from the right-wing-bait material and did what he does best—talk about race, class and power structures in America—the results were spectacular. Look no further than his incendiary 27-minute set 8:46 (2020), named after the duration of time ex-cop Derek Chauvin knelt on George Floyd’s neck.

Does his latest special, The Dreamer, undo the damage? Yes and no. This new, 57-minute special (released on Dec 31 by Netflix) contains a number of well-crafted longform stories, jokes-within-jokes stacked like Matryoshka dolls. And yet, Chappelle simply cannot resist reverting to recent form every 10 minutes or so, needlessly shoehorning what he clearly thinks are gotcha moments aimed at trans, gay and disabled people. “I love punching down,” he declares at one point, right after he mimes a physical handicap (he does this five or six times through the show). Weird flex but okay, Dave.

The first 15-20 minutes of the show set up the pattern it will follow throughout. Chappelle talks about being stuck in a dark place following the death of his father, and how the late Norm Macdonald helped him get out of this rut. It’s good, sturdy, funny-sad stuff and Chappelle builds up to a lovely little anecdote about Macdonald inviting him to the set of the film Man in the Moon, where Jim Carrey played the lead role, that of the comedian/entertainer Andy Kaufman. Being a huge Jim Carrey fan (“he has the kind of God-given talent that you cannot rehearse for or practice”), an excited Chappelle immediately agreed. When the day finally arrives, it turns out Carrey is in extreme method-acting mode, walking and talking like the late Kaufman.   

“I wanted to meet Jim Carrey, but I had to pretend this n**** was Andy Kaufman. All afternoon. And he was clearly Jim Carrey. I could look at him and I could see that he was Jim Carrey,” Chappelle says. Up until this point, this extended joke is working fairly well, two spoons slapstick with a dash of oddball humor. And then the world’s shittiest hammer drops. “Anyway, I say all that to say: That’s how trans people make me feel.” Really, Dave? That’s some weak sauce right there. It’s unfunny and repetitive and doesn’t even work as the ‘anti-punchline’ it so desperately wants to be. 

Chappelle has become the ignoble, alcoholic baap of the comedy world and The Dreamer is another frustrating reminder of both his undoubted skills and his spiraling descent. 

About 25 minutes in, Chappelle says that he has been working on a play about a black trans woman. “(…) It’s a tearjerker. At the end of the day, she dies of loneliness because white liberals don’t know how to speak to her.” This is classic strawman stuff, not least because the “white liberal” framing is an erasure of the very real and on-point critiques Chappelle has received from queer and trans Black people.

In the second half, Chappelle once again flatters to deceive. The last 20-odd minutes of The Dreamer are devoted to the titular concept—Chappelle’s belief that “[…] in any given moment, the most powerful dream wins”. There’s a very funny story here about Chappelle surviving a tense encounter with Russian mobsters immediately after his first HBO special Killin’ Them Softly (2000). There are subtle ideas explored here, like the joke where he says that “being right all the time” is its own special category of intoxicant. It’s an interesting thought, which Chappelle then artfully links this passage to the Will Smith/Chris Rock ‘Slapgate’, specifically his non-judgmental, take-no-sides stance (despite being close friends with Rock).

“[…] That’s why I don’t judge between Will Smith and Chris Rock. Because you guys look at them as big ideas but I look at them as fellow dreamers. I can’t judge between them because I see myself in both of them. I am Will Smith. I am the man that cannot take it anymore and will slap the shit out of the next person that says a cross word to me or somebody that I love. And I am Chris Rock. I am the man that can get slapped in front of the whole world and keep my composure so I don’t fuck anything up. That is what men do. Men make boundaries. Men enforce boundaries. And men test boundaries.”

This is, I am sure you will agree, much closer to peak Chappelle than most of his recent stuff. But no, he has to go and ruin it with another wannabe ‘anti-punchline’. “And no man tests more boundaries than a trans man.” Mic drop? More like terminally-online cerebral edema—let’s call it ‘mic-dropsy’. 

What do comedy fans do with the problem that is Dave Chappelle? What does Dave Chappelle do with the problem that is Dave Chappelle? I’m not entirely sure. But the impossible-seeming convergence of circumstances—an artform’s premier exponent morphing into its silliest/meanest one—reminds me of an old Amitava Kumar interview (with journalist Jai Arjun Singh) where the writer talks about his frustration with Salman Rushdie’s diminishing results down the years, something Kumar viewed as Rushdie slowly becoming a “Page 3 writer”.   

“[…] He’s a very important figure for us (contemporary Indian authors working in English). Baap hai woh. Aur baap ko gaali dena buri baat hai. Lekin chutiya baap hai. Baap agar roz daaru peeke ghar aayega toh aap usko kitna respect denge?”

Chappelle has become the ignoble, alcoholic baap of the comedy world and The Dreamer is another frustrating reminder of both his undoubted skills and his spiraling descent.