His stage persona has changed too, with less animated physicality and a faster, raspier delivery. Mr. Chappelle’s jokes once moseyed before they exploded. They’re steadier now, quicker to start, but less likely to dart off in wild directions. And his voice doesn’t range as much, staying in a deeper register. Some of his agility and mischievousness has been replaced with an increased narrative ambition, rooted in a confidence in his ability to get a laugh so firm that he goes deep into ideas without a punch line. This strategy has risks, which he not only embraces but also luxuriates in.
As he often does, Mr. Chappelle tells a story of getting booed onstage — this time it was about a show in Cleveland after making a joke about a killer at large there (along with the nearly-as-provocative admission that he’s a Warriors fan). Another time, he introduces a bit about Michael Jackson by saying it’s not going to work. (It did O.K., but not nearly as well as his jokes on the same material from his 2004 special “For What It’s Worth,” one of the best this century has produced).
Mr. Chappelle likes the high-wire act of comedy, using the tension produced by wading into polarizing, treacherous material to set up the release that laughter provides. It’s why he has long avoided taking on Rachel Dolezal (he says it’s too easy), but in one of his funniest tangents, he confesses he can’t stop thinking about her. It’s no surprise that the comedian who started the first episode of “Chappelle’s Show” with a sketch about Clayton Bigsby, a black blind man who thinks he’s white, is drawn to a white woman who identifies as black.
Mr. Chappelle asks emphatically: How far is Ms. Dolezal willing to go to become black? “Are you willing to refinance your house,” he says, pausing for the first wave of laughter before finishing the sentence, “so you can invest in a mixtape that won’t pan out?”
No comedian has done more confident and nuanced work about the fluidity of race; think of his inspired “racial draft” sketch, which began with an idea from Bryan Tucker, the current co-head writer of “Saturday Night Live.” But Mr. Chappelle finds himself on more unsure footing when it comes to gender. In his recent Netflix special, he drew considerable criticism for his jokes about transgender people in which he took umbrage at having to change his “pronoun game” for what he referred to crudely as someone else’s “self-image.”