Stream It Or Skip It: ‘Dave Chappelle: The Dreamer’ On Netflix, Where The Comedian Has Fulfilled His Lifelong Dream If Not Also Yours

Dave Chappelle just doesn’t know when to quit. After claiming he’d said all he needed to in 2021 with The Closer, he has come back with a Grammy-nominated lecture to students and now this performance which finds him at 50 looking back at where he started in Washington, D.C., at 14, and on the same stage where he filmed his first hour special for HBO back in 2000. Is it full circle? Or is he merely spinning his wheels at this point?

DAVE CHAPPELLE: THE DREAMER: STREAM IT OR SKIP IT?

The Gist: Since releasing his first specials on Netflix in 2017, Chappelle has now amassed Grammys for all four of his previously releases on the platform, and Emmys for two of them. He also has won the Mark Twain Prize for American Humor, earned multiple Emmy nominations for his visceral reaction to the murder of George Floyd in 2020 (8:46, released on Netflix’s Netflix Is A Joke YouTube channel), and currently up for the Grammy for Comedy Album of the Year for What’s In A Name? his speech to students at his alma mater, Duke Ellington School of the Arts.

What’s left for him to say now? Chappelle wanted to return once more to D.C., to the Lincoln Theatre where he filmed his breakthrough debut in 2000 for HBO, Killin’ Them Softly, and look back on how far he has come since then. Because ultimately the dream is the one he’s living now.

And also more jokes about trans people, plus Chappelle’s own thoughts on Will Smith slapping his comedy buddy Chris Rock at the Oscars, and how a few months later, an audience member bum-rushed Chappelle onstage at the Hollywood Bowl. That wasn’t so dreamy.

What Comedy Specials Will It Remind You Of?: Coming hot off the heels of Ricky Gervais: Armageddon six days ago, there are obvious comparisons as both Gervais and Chappelle have hit huge paydays with Netflix while also doubling down on jokes about marginalized people. But the main content of this set from Chappelle contains even more parallels to Chris Rock and directly references Rock’s live Netflix special from earlier in the year.

Memorable Jokes: Chappelle opens with a story about how the late Norm Macdonald tried to cheer him in the late 1990s by introducing the young comic to one of his idols, Jim Carrey, only to realize this meeting took place on set of filming Man On The Moon, wherein Carrey never broke character as Andy Kaufman. Having to pretend Carrey was Kaufman was a big letdown to Chappelle, who now tags it with the line: “Anyhow, I say all that to say, that’s how trans people make me feel.”

Yep. There will be more trans jokes. “If you came here to this show tonight thinking that I’m gonna make fun of those people again, you’ve come to the wrong show,” Chappelle says, only to renege on that claim, as well as one quickly thereafter that’s more clearly a joke about how he’s “doing all handicapped jokes.” (There is a shot of former Congressman Madison Cawthorn, a target of some of these jokes, doubled over laughing during the end credits). Instead, Chappelle quips he’ll repair his relationship with the LGBTQ+ community by writing a play about a black trans woman whose pronoun is the N-word, then claims if he went to jail in California, he’d identify as a woman to take advantage of the other inmates.

On a relatively lighter note, Chappelle lets us know why he still prefers to visit strip clubs alone (despite being married with grown children), and gurgles out an impersonation of Titanic drowning ghosts reacting to the Titan submersible implosion earlier this year.

He’s got 15 minutes or so about reacting to “The Slap,” only to have his own onstage incident a couple of months later at the Hollywood Bowl, and then this year watching Rock’s take on it all in his Netflix special in Baltimore.

And then he’s got another 15 minutes that he stages as an encore, asking for but not receiving a standing O while he briefly left the stage to take off his outer shirt and grab a cigarette to smoke. Then sitting on the stool, Chappelle recalls an incident in San Francisco while he was taping his 1998 half-hour special for HBO, and having it rudely interrupted by music coming from the venue downstairs from the taping. What that has to do with meeting Lil Nas X in the present day, you’ll have to find out for yourselves.

Our Take: It’s all too easy to get hung up on Chappelle’s trans jokes because the subject somehow remains a hang-up for him.

Is it because at 50, he still hasn’t matured from the 14-year-old who started comedy? Is it somehow connected to his preference to still attend strip clubs by himself? Or perhaps it’s really as simple as the story he chose to tell at the start of this set, about wanting to meet Jim Carrey only to realize he was meeting Carrey during his method-acting performance as Kaufman? Chappelle cannot help but turn it into the first of many more jokes at the expense of trans people. But what if he were telling us something about the Chappelle we’ve been seeing on Netflix these past six years? What if this Chappelle isn’t the comedian we all remembered and loved, but rather himself a Kaufman-esque character designed to antagonize us?

What if that’s all this is, that Chappelle himself is a thoughtful, loving, caring human, but when he’s onstage, he’s turned wrestling heel? And that shirt with his name on it and the big C logos onstage and elsewhere are all just part of his costume, that he’s so immersed in this transphobic caricature than he cannot break character even just to let us know he doesn’t mean any of it?

Or is this giving him too much credit? After all, he did tell us that he has been labeled as a laxy comedian who works nonstop, and he did defer to his colleague Rock, calling Rock “the greatest living comedian,” for a moment humbling himself out of all of that previous GOAT talk about Chappelle.

Our Call: I wish Netflix added chapters so I could urge you to SKIP AHEAD to the stories and avoid all the unnecessary transphobia. And I’d note that much like Gervais does in his special last week, Chappelle admits in this set that certain jokes his wife hates and wishes he wouldn’t tell. But as he also says: “You have to be wise enough to know when you’re living in your own dream, and you have to be humble enough to accept when you’re in someone else’s.” This Netflix contract with Chappelle is his dream, not ours.

Sean L. McCarthy works the comedy beat. He also podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.