Dave Chappelle does not make it easy.
He is one of the most brilliant stand-up comics in the business. But he also makes a sport of challenging his audience — putting ideas in front of them that he knows are uncomfortable and unpalatable to those invested in modern notions of how to talk about feminism, gender, sexual orientation and race.
Sometimes, he does it to make a larger point. But at times, especially during his latest special for Netflix, The Closer, he also seems to have a daredevil's relish for going to dangerous places onstage and eventually winning his audience over — regardless of what he's actually saying.
Of course, these days, the fix is in. Chappelle is considered the Greatest of All Time among many comedy fans — he says it about himself, wryly, toward the end of the special — and The Closer finds him surrounded by an enthusiastic audience in Detroit ready to go wherever he takes them.
That much is obvious, early in the special, where he talks about an idea for a film centered on an ancient civilization that discovered space travel, left the planet and then came back, determined to claim the Earth for their own. His punchline is the title for the film: Space Jews.
Even the adoring audience in Detroit took a breath on that one. "It's gonna get worse than that," Chappelle retorts, laughing. But I'm not sure it did. Because that was pretty awful.
Coming from Chappelle, a joke like that felt like a dare. He knows, in the moment, that such a punchline will briefly break the spell he has on the audience, make them rethink their allegiance to him, at least for a second. And he'll have to work a little to get them back on his team again — which he does.
(He also knows reviewers like me will quote the joke and criticize him for it, which I am. I don't really care what point he's trying to make; a joke that sounds like antisemitism gets a hard pass from me.)
And the message Chappelle has for those who have criticized him about transphobic, homophobic or any other phobic jokes seems to be: Race trumps all.
This idea surfaces when he talks about rapper DaBaby, who was pilloried publicly for making homophobic comments during a concert in July. Chappelle jokes that DaBaby "punched the LGBTQ community right in the AIDS" before recalling a 2018 incident in which the rapper was involved in a fight inside a North Carolina Walmart where another person was shot and killed.
"In our country, you can shoot and kill a n*****," Chappelle says. "But you better not hurt a gay person's feelings."
What Chappelle doesn't say is that DaBaby claims he was defending himself against two men who tried to rob him and his family in the store. Eventually, he was found guilty of a misdemeanor charge — carrying a concealed weapon — though the family of the 19-year-old who died insists that DaBaby started the fight.
In The Closer, Chappelle eventually says he's jealous of the progress the gay rights movement has made in America. "If slaves had oil and booty shorts on, we might have been free 100 years sooner," he cracks.
But lines like that assume that the struggle over oppression is a zero-sum game — that because some gay people have access to white privilege in America, all their concerns about stereotyping and marginalization are hollow and subordinate to what Black people face.
It ignores the fact that there are plenty of nonwhite gay people who face oppression for both their sexual orientation and their race. And, of course, opposing these public statements of homophobia isn't just about making gay people feel better; it's about keeping the anger and prejudice behind those words from becoming widely acceptable or turning into action.
Too often in The Closer, it just sounds like Chappelle is using white privilege to excuse his own homophobia and transphobia.
Because Chappelle is brilliant, his words about DaBaby make an important point; it is sad that more people know about DaBaby's homophobic comments than his involvement in this deadly encounter. But there is more to the story outside his simplistic framing, which seems designed to excuse some pretty hurtful words.
"Gay people are minorities until they need to be white again," Chappelle says as the capper to a different story about his conflict with a white man who called the police. The comic says the man he nearly fought was gay.
And, yes, we know what calling the police on a Black man can mean in a post-George Floyd world. But if some belligerent jerk were confronting me in a nightclub, I'd probably call the cops, regardless of the race of the jerk. And Chappelle refuses to consider this possibility.
He goes on to joke that for years, he thought the word "feminism" meant "frumpy d**e." That the #MeToo movement was "silly" because wealthy women in Hollywood didn't fire their agents and uplift women working in the mailroom. That, just when he figured out how to nail white people on their racism, some white people changed the game by declaring they were changing genders.
Chappelle recalls how he once asked why it was easier for Caitlyn Jenner to transition in public than for Cassius Clay to change his name to Muhammad Ali, ignoring the obvious answer: Ali adopted his name 50 years earlier. Thankfully, times also eventually change.
The fact is, these are all complicated topics, tough to encapsulate in a single punchline or anecdote. And watching Chappelle talk about them is like watching somebody use a chain saw as a letter opener.
Worse, it is obvious during The Closer that Chappelle cannot stand dealing with people who confront him over his more controversial jokes. More than once, he relays a story about someone getting in his face about how he has talked about women, gay people or transgender people, accusing him of "punching down."
Chappelle may craft his monologues to make the audience think. But that doesn't mean he necessarily wants much of a dialogue, especially with people who don't like his ideas.
The Closer ends with a poignant story about transgender comic Daphne Dorman, whom he befriended and allowed to open for him during a club appearance in San Francisco back in 2019. Dorman died by suicide that same year; Chappelle says she took a lot of criticism online for defending him against allegations that he was transphobic and for denying he was "punching down" in his material.
Earlier, Chappelle says this performance, his sixth special with Netflix, will be his last for a while. He also says he won't joke about LGBTQ topics anymore.
"I'm done talking about it," he says toward the end of The Closer. "All I ask of your community, with all humility: Will you please stop punching down on my people?"
That line, with all of its terrible assumptions about who "your community" is and who "my people" are, just made me terribly angry and disappointed. Because untangling homophobia, transphobia, racism and white privilege requires a lot more effort and understanding than Chappelle makes here.
But if I were gay and heard a line like that from a wealthy, Emmy-winning comic at the end of a special that millions of his fans will likely watch and cosign, I'd probably have a simpler response: