The wildest moment in the new Dave Chappelle special, “The Dreamer” (Netflix), arrives about two-thirds of the way through when the comic says he’s about to tell a long story. That’s not the unusual part.
Some 36 years into a storied comedy career, Chappelle, 50, is better known for controversial yarns than carefully considered punchlines. At this point in the special, he tells the crowd in his hometown, Washington, D.C., that he is going to get a cigarette backstage, asks them to act as if he were finished and says he would prefer a standing ovation. He then does something I have never seen in a Netflix special: He walks off for a smoke and costume change, leaving the stage empty. He strolls back as everyone waits, politely clapping. No one stands. He sits down and even mentions that he didn’t get the standing ovation, grumpily.
He could have cut that out but didn’t. Why? Was it to reveal that his crowd refused to be told what to do, how he doesn’t mind, as he said at another point, if most people didn’t laugh at some jokes? Was it to include a momentary reprieve from the self-aggrandizing tone of the hour, which begins with rock-star images of Chappelle walking to the stage in slow motion and ends with a montage of him with everyone from Bono and Mike Tyson to the Netflix C.E.O. Ted Sarandos? I have no idea, but what sticks with you in Chappelle’s sets these days is less the jokes than the other stuff, the discourse-courting jabs, the celebrity gossip, the oddball flourishes.
Later, Chappelle says, “Sometimes, I feel regular.” As an example, he describes being shy at a club where a rich Persian guy surrounded by women recognizes him and the comedian imagines him telling the story of seeing Dave Chappelle the next day. The idea that this is Chappelle’s idea of regular is funny.
The last time he released a Netflix special on New Year’s Eve was in 2017, which now appears to be a turning point in his career. After vanishing from popular culture for a decade, Chappelle came out with four specials that year, a radically productive run that was the start of a stand-up phase that would grow to overwhelm the memory of his great sketch show, which then dominated his legacy.
“Chappelle’s Show,” now two decades ago, began with a brilliant sketch about a blind Black white supremacist named Clayton Bigsby. It was inspired in part by Chappelle’s grandfather, a blind man named George Raymond Reed, who had served on the D.C. mayor’s commission for the disabled. Reed was funny. His Washington Post obituary reported that in describing how to spell his name, he would joke: “Reed with no eyes.”
Back in 2017, Chappelle began making jokes about transgender people — and he hasn’t stopped, in special after special, show after show. How you feel about this fixation is baked in, at this point. He begins his new hour with a labored trans joke, before saying he’s finished making them. (Fat chance: They are as much a part of his brand as his name on his jacket.) Then he says he has a new angle: disabled jokes. “They’re not as organized as the gays,” he says. “And I love punching down.”
He covers other topics. There’s a big set piece about Chris Rock getting slapped at the Oscars, the most popular subject of 2023 in comedy, and he does some cheap racial jokes, like an elaborate bit merely meant to set up his doing an Asian voice.
At one point, he tells the audience that people in comedy think he’s lazy because he’ll tell a joke for a crowd of 20,000 that makes only two or three people laugh, but they will laugh hard. He goes on to tell that joke, an impression of the dead people on the Titanic seeing the doomed OceanGate submersible coming toward them, and it’s silly and fun, a throwback to earlier days. The truth is the more common criticism you hear these days is not that Chappelle aims for a niche but that he seems to prefer making points to getting laughs.
This happens to some star comics. This month, Ricky Gervais released a dutifully predictable collection of jokes about supposedly taboo subjects. That special, “Armageddon” on Netflix, makes Chappelle look fascinating and unexpected by comparison.
Gervais trots out complaints about people being easily offended, before setting up bits that lean so hard on the assumption of that response that there isn’t much more to them. His fans eat it up. But what’s striking about his hour is the justifications, the defensive explanations, the spelling out of themes. Fine, make your Holocaust and pedophile jokes. But how about: Show, don’t tell.
Comedy is a crowded field, but for most audiences, it’s still defined by its biggest stars. Chappelle and Gervais are part of that elite, and the distance between them and the rest of the stand-up world feels greater than ever. That growing inequity is one of the subjects of Gary Gulman’s new special, “Born on 3rd Base” (Max), a meticulously funny hour that digs into the gap between the haves and have-nots.
He attacks this subject in a variety of ways, in jokes dissecting the comedy world, an inspired bit about how people order at Chipotle and a rebuttal to the argument that welfare payments destroy initiative. As different as Gulman is from Chappelle in the choice of targets, style and level of fame, they share some qualities. Gulman, 53, also likes jokes that only some will get, and he has a distinct sense of timing that insists on the crowd adjusting to him. He begins his special with the word, “Anyhow.” Is he in the middle of a thought or the end? Either way, we’re disoriented. He likes us there. He plays at his own off-kilter pace.
One tactic is the stop-and-go move of slowing down to let his viewers get ahead of him. He announces he has a one-man show called “Mommy, Look,” and the title, he explains, stems from his theory of “just about every one-person show.” Then he pauses and holds, and the crowd laughter grows as they anticipate his point about the origin of the artistic impulse. “You show me a 4-year-old on a diving board to an unreceptive audience,” he says, “I will show you a theater major.”
But Gulman also likes to get ahead of his audience, with language-drunk sentences, references intended to be over some heads (“bandicoot,” “paramecium”) and others that wallow in wordplay. One gets the sense that he has whole jokes that are, among other things, an excuse to say words like “burglar” or “guillotine.”
This is the only special that dares to engage in this debate: What is the most pretentious suffix in the English language?
You’ll have to watch to find out. But the second most pretentious, he argues, is “-esque,” before qualifying the point in the most pretentious way possible: “Unless you’re talking about something French.”
“I pander to my base,” Gulman confesses, “which is librarians.”