But the time spent on this subject is overshadowed by his other favorite long-running pastime, expressing sympathy for rich and powerful men enmeshed in scandal. Chappelle has become the bizarro Joan Rivers, obsessed with celebrities, but not to skewer them so much as to play their defense attorney.
In his new show, he does Louis C.K. few favors by defending him limply. He also speaks up for Kevin Hart who, in his telling, lived a blameless life when his dream of hosting the Oscars was dashed because of a few tweets. And after litigating the case of Michael Jackson on specials in 2004 and 2017, he does so again here, telling his audience not to watch the recent HBO documentary, “Leaving Neverland,” in which two men who accused Jackson of sexual abuse speak out. Chappelle says he doesn’t believe them, and then adds that he has no evidence, before sputtering that even if the pop star was guilty, “he’s Michael Jackson.”
As he has told audiences many times, Chappelle says he is not in “the being right business.” He often adds qualifications to these provocations, but it’s hard not to notice that he sympathizes so much with his peers in wealth and fame. Once again returning to what he sees as the excesses of #MeToo, which he has soured on even more than in his special in 2017, when he described victims as “weak,” he focuses on the plight of the men, those accused, but also the ones who might be. Chappelle refers several times to the dangers of being canceled. He’s not worried, he says, because he doesn’t rape, but adds: “I have a few Aziz Ansaris in my past.”
The extensive Playbill bio noted that Chappelle’s comedy has “often shocked his audiences into laughter.” But there’s nothing shocking anymore about his making fun of transgender people. He does it so relentlessly that it has become blandly familiar. And the way he pairs this material with constant justifications, explaining how these marginalized groups, which he calls “the alphabet people,” have disproportionate power in Hollywood, is defensive, predictable and ultimately cruel.
Chappelle would argue, rightly, that comedy contains cruelty, and no one has demonstrated the comic potential of punching down better than him (see his sketch about beating a kid with cancer in a video game on “Chappelle’s Show”) But the bar for such jokes is higher, and he doesn’t scale it.
Of the dozen or so times I have seen Chappelle headline, this show was the first where I occasionally felt bored. Make no mistake, he remains such a naturally funny performer that he is always worth seeing. And where his greatest gift was once the conspiratorial way he would introduce an idea, teasing an audience by saying he probably shouldn’t say something, now his signature is to bring up something ridiculous and flash some side-eye.
He uses it to particularly sharp effect to mock Jussie Smollett, the rare disgraced celebrity he displays little sympathy for. Imagining the police hearing Smollett’s story that he was attacked by men wearing MAGA hats in Chicago, Chappelle flashed that side-eye before imitating an officer excusing himself and saying to a colleague: “Find out where Kanye West was last night.”