Dave Chappelle Mostly Moves on From Troll to Philosopher in ‘The Dreamer’

Despite the occasional misstep, Chappelle rediscovers empathy
Dave Chappelle Mostly Moves on From Troll to Philosopher in ‘The Dreamer’

In Dave Chappelle’s new Netflix special, The Dreamer, it’s almost as if he has to get the “you can’t tell me what to say’s” out of his system before he can get to the good stuff. He turns his opening story about meeting Jim Carrey on the set of Man in the Moon into a toothless trans joke before vowing to leave the subject alone for the rest of the night: “If you guys came here to this show tonight thinking that I’m going to make fun of those people again, you’ve come to the wrong show.” 

It’s a promise Chappelle mostly keeps, although he can’t resist also throwing in a few disabled gags, joking that he loves punching down. Luckily, Chappelle proceeds to right the ship just as The Dreamer threatens to become a partner piece for Ricky Gervais’ defensive and driftless Armageddon.

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Chappelle’s new special sees him returning to the scene of an almost-crime, his hometown of Washington, D.C.. It’s the city where he filmed his first half-hour special for HBO when he was only 22 years old. Now 50, Chappelle appears to relish the full-circle moment of coming back to where he started, setting the tone for an evening of comic reflection.

There’s a surprisingly fresh bit about Chris Rock being attacked by Will Smith at the Oscars, a subject that’s been, well, beaten into the ground by other comedians. But Chappelle has an interesting twist: He’s probably the only comedian who knows exactly how Rock feels. That’s because Chappelle was assailed himself just a few months later during a live comedy set at the Hollywood Bowl. You think you know what you would have done if Will Smith came for you on a stage? Chappelle assures us that we don’t — no one does until they’re faced with violence themselves. (He’s still mad at Rock for running on-stage with the best joke in the aftermath of the Chappelle attack: “Was that Will Smith?”)

The Dreamer's signature bit — the one that should get all the attention if Chappelle’s annoying habit of dropping the occasional gay joke doesn’t — is a long story he tells to end the show. It’s a tale about that first HBO showcase when he was 22, a production that was nearly derailed by a disturbance outside the club where Chappelle was filming. It felt like a dream destroyed, and in his fury, the young comic found himself in a confrontation that could have ended his career then and there. Like the best Chappelle stories, it’s equal parts funny, frightening and unexpected. It’s also inspirational. “Believe in your dreams” isn’t the most original advice in the world, but the comic finds a way to give it new juice. It’s also a reminder about the importance of humility and the role we play in each other’s dreams.

Despite being great friends with touring partner Rock, Chappelle says he can’t judge Rock or Will Smith because he sees himself in both men. He is both the man who can’t take it anymore and the man who can get slapped in front of the whole world. It’s empathy that went sadly missing in specials like Sticks & Stones and The Closer and a relief to see Chappelle back in touch with that part of his comedy. 

There’s still no excusing the handful of trans and gay jokes that dot the special, half-hearted punchlines as lazy as they are unnecessarily goading. But because Chappelle has rightly reshifted his focus from provocateur to philosopher, The Dreamer feels like a step forward.

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