Dave Chappelle: The Dreamer, the comic’s seventh stand-up special for Netflix, opens with a quote about the nature of success by Henry David Thoreau before capturing the comic in stark black-and-white, moving through the crowd in slow-mo (cigarette in hand, naturally) to Radiohead’s “Daydreaming,” like a championship boxer before a fight. We’re at the Lincoln Theatre in Chappelle’s hometown of Washington, D.C., the very place where he filmed his first stand-up special, Killin’ Them Softly, 24 years ago. Quite a lot’s changed since then, as the 50-year-old is quick to point out. He had to hand out tickets on the street to fill it in those early days; now, fans clamor for them. Now, he’s the biggest stand-up comedian in the world, whose specials are less joke-y and more of the storyteller variety.
His nostalgia for the venue soon gives way to a personal story about his father passing away before he could witness that initial special, and a nod to late comedian Norm Macdonald for helping him feel excitement and enthusiasm again by inviting him to the set of Man on the Moon to meet one of his comedy idols, Jim Carrey. Unfortunately, since Carrey was in character as Andy Kaufman the entire time, Chappelle was left frustrated and disappointed. It’s a funny little trip down memory lane — that is, until the punchline: “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. Anyway, I say all that to say: That’s how trans people make me feel.”
He smiles from ear to ear, proud of the dig, before exclaiming, “Here we go! Now, if you guys came here to this show tonight thinking that I’m gonna make fun of those people again, you’ve come to the wrong show. I’m not fuckin’ with those people anymore. It wasn’t worth the trouble. I ain’t sayin’ shit about trans people. Maybe three or four times tonight, but that is it. I’m tired of talkin’ about them. And you wanna know why I’m tired of talkin’ 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 comin’. I ain’t doin’ trans jokes no more. You know what I’m gonna do tonight? Tonight, I’m doing all handicap jokes. Well, they’re not as organized as the gays, and I love punching down.”
Chappelle says he’s tried to “repair his relationship with the transgender community” and did so by writing “a very sad play, but it’s moving” about “a Black, transgender woman whose pronoun is, sadly, n*****. 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.”
There’s more, of course, including a joke about how if he were convicted of a crime, Chappelle would claim he identifies as a woman so he could be sent to a women’s prison and make the inmates “suck this girl dick I got and don’t make me explain myself” — this particular line sends him into a giggle fit onstage.
It’s unfortunate that Chappelle’s The Dreamer is, like some of his prior Netflix specials, so obsessively fixated on the trans community, because it’s not an area he particularly excels at, resorting to puerile premises and punchlines. There are, of course, ways to artfully tell a trans joke — take Michelle Wolf’s recent Netflix special It’s Great to Be Here — but Chappelle is apparently incapable of having most of his bits extend beyond mocking genitalia or pronouns. It’s not just tired but uninspired.
It’s a relief when, after a 15-minute barrage of trans jokes to open the special (with a dig at former congressman Madison Cawthorn’s paraplegia thrown in for good measure), Chappelle segues to different material, such as a fun little story about why he likes to go to strip clubs alone, his reaction to Will Smith slapping the piss out of his pal Chris Rock at the Oscars, and his own brush with an onstage assailant at the Hollywood Bowl, resulting in all of Chappelle’s celebrity friends whooping the intruder’s ass.
I’ve never been in a situation that extreme. But I do know now what Will Smith would not have done: And that is, enjoy the rest of his evening.
“People would ask me all the time. They’d say, ‘Dave, what would you do if you were Chris Rock and Will Smith slapped you in the face?’ And to this day, the answer’s the same: Well, I don’t know what I would’ve done. I’ve never been in a situation that extreme. But I do know now what Will Smith would not have done: And that is, enjoy the rest of his evening,” he says.
The frustrating thing about Chappelle’s preoccupation with the trans community is that he’s still capable of spinning a hilarious, layered yarn when he wants to that will have you in stitches. But he just can’t help himself.
Chappelle concludes The Dreamer with a long story about how his second stand-up special went awry involving a nightclub, loud music, bad producers, and Russian mobsters. The moral of the story is that he’s a “powerful dreamer” and has realized his dream, and that it’s important to live your own dream and not be a supporting character in someone else’s, or to allow circumstances to defer that dream. It should be a powerful and moving moment, seeing this legendary stand-up comedian reflecting on his journey and how far he’s come, and is followed by a black-and-white glimpse at Killin’ Them Softly. Chappelle, however, can’t even do this without shoehorning in a shot at trans men.
