You’d think that Chappelle, a megastar Black male comedian who’s toured as a coheadliner with Rock, would have something funny, interesting, or perhaps profound to say about the incident. The best he can muster? “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.” Groundbreaking.
Part of the trouble with Chappelle is that he still shows flashes of brilliance—something I noted when writing about the very strange night of comedy that transpired before Chappelle was bum-rushed by a weapon-wielding assailant. In The Dreamer, Chappelle transitions from jokes about the Slap to jokes about his own attack, briefly resembling the comedian he once was. He’s relatable when admitting that the incident was “some scary shit,” and makes a genuinely funny joke about how bodyguards probably shouldn’t wear dress shoes to work. (His own security guy, Travis, “came out slipping and sliding in some kind of beautiful loafer and fell flat on the back.”) But what starts as a promising anecdote quickly devolves into Chappelle’s preferred comedic crutch, as he starts cracking jokes about his alleged assailant’s sexual orientation. “Bisexual?” Chappelle says, feigning shock. “I could have been raped!”
“I’m what’s known as a lazy comedian,” Chappelle says at one point during The Dreamer. “They call me lazy ’cause I do shows sometimes—20,000 people be in the crowd, and I’ll tell a joke, and they’ll all look at me like I’m crazy. But three or four people will laugh really hard. And I’ll be onstage like, Yeah, that’s good enough.” It’s meant to read as a joke, but throughout the special, it feels more like an admission.
In his book, Comedy Book, writer and Good One podcaster Jesse David Fox chronicles the diminishing returns of Chappelle’s LGBTQ+ jokes—how they’re unsuccessful not because they’re offensive, but because they’re so rote. “Predictable to anyone paying close enough attention,” Fox writes, “it makes both the slow buildup, where he occasionally tries to sneak in some sort of message, and the inevitable twist so incredibly boring.”
Nowhere is this more clear than in the latter half of The Dreamer, where Chappelle does a long, meandering bit about dreams that ends with a punch line involving an elementary-school-aged Lil Nas X proclaiming that his dream is to be “the gayest n-gga that ever lived.” Fox couldn’t have predicted it better if he had a crystal ball.
Comedy specials are filmed well in advance of when they air; they’ll never be as up to the minute as a TikTok. Comedians are expected—required, even—to repeat the same material to perfect it, and some jokes are, in fact, timeless. But when a once great comedian keeps grinding the same axe while insisting on his own bravery, it’s hard to keep watching.
“I’m tired of talking about them,” says Chappelle of the trans community in The Dreamer. “And you wanna know why I’m tired of talking about ’em? Because these people acted like I needed them to be funny. Well, that’s ridiculous. I don’t need you. I got a whole new angle. You guys will never see this shit coming.” The funny thing is, anyone can see it from a mile away.