Watching Dave Chappelle’s monologue on “Saturday Night Live,” I forced myself to follow the same advice I give to students in my class about comedic controversies: “Laugh if you find it funny. Then ask (lots of) questions.” 

Did I find Chappelle’s acidic riffing on Ye’s recent antisemitic episodes funny? Momentarily, yes. But only so long as I wasn’t overcome by a pressing need to ask lots of fevered questions. Questions like: What on Earth was Chappelle thinking as he performed an endless set of cringe-y jokes about Jews for an audience of millions? When will Chappelle ever learn that what for him is just the harmless exercise of his free speech is, for others, speech that might have terrible consequences? Why, after having lit up “the Jews,” couldn’t Chappelle resist the temptation to take another swipe at the LGBTQ community? And — isn’t it ironic? — did Otis Redding’s “Try a Little Tenderness” really serve as the walk-on music as Chappelle took the stage? 

Although Chappelle was commanding the biggest stage in American comedy, he nevertheless seemed concerned that he was about to be silenced.

Tenderness was nowhere on display in this set. Nor was the kind of comedic common sense that so many other stand-ups are learning to apply as their art form undergoes radical changes. 

Let’s start with the Jewish gags. Throughout his lengthy set, Chappelle kept reverting to the same formula. First, he would earnestly denounce antisemitism or seek to dispel antisemitic stereotypes. Then came the comic clawback, the punchline in which he affirmed the truth of the slurs he just decried. Throughout it all, he implied that these truths about “the Jews” cannot be spoken aloud (whether that is because of wokeness or the Vengeful Wrath of the Mighty Jews was left unanswered).

Chappelle launched his barrage with a somber announcement: “I denounce antisemitism in all its forms. And I stand with my friends in the Jewish community.” To which anyone who knows his formidable body of comic mischief was likely to gasp, “Uh-oh.” With the first part of the joke rendered, he went in for the kill by offering this wise counsel to Ye, formerly known as Kanye West: “And that, Kanye, is how you buy yourself some time.” (Please note Ye sampled Redding’s “Try a Little Tenderness” on his track “Otis,” which perhaps accounts for the choice in musical accompaniment to Chappelle’s entrance.) 

Continuing to reflect on Ye’s repeated collisions with the (Jewish) entertainment industry, Chappelle mused: “He had broken the show business rules. … You know, the rules of perception. If they’re Black, it’s a gang. If they’re Italian, it’s a mob. If they’re Jewish, it’s a coincidence, and you should never speak about it.” The wordplay here is as clever as it is insidious. The bit implies that when dealing with unscrupulous Jews, one is forced to pipe down and pretend that their control of the industry isn’t real.

Lest there be any doubts about which group rules show business, Chappelle minced no words. “I’ve been to Hollywood. … This is just what I saw.” With his uncanny timing, he paused and nearly whispered: “It’s a lot of Jews.” Pause again. “Like, a lot!” “But it doesn’t mean anything,” he assured us — “there’s a lot of Black people in Ferguson Missouri; doesn’t mean they run the place.” Translation: While powerless African Americans languish in Ferguson, where they are subject to systemic racism, powerful Jews run Hollywood.

Warming to his theme and clinging to his formula of denial and then winking affirmation, he commented: “You could maybe adopt the delusion that Jews run show business. It’s not a crazy thing to think.” And then he followed up with: “But it’s a crazy thing to say out loud, in a climate like this.” 

The comedian peaced out with a veiled poke at his many critics in the LGBTQ community and their allies. Although Chappelle was commanding the biggest stage in American comedy, he nevertheless seemed concerned that he was about to be silenced. He sighed: “It shouldn’t be this scary to talk. About anything. It makes my job incredibly difficult to be honest with you. I’m getting sick of talking to a crowd like this. I love you to death, and I thank you for the support. And I hope they don’t take anything away from me. Whoever they are.” For those who are familiar with Chappelle’s controversial “The Closer,” the reference to “they” is unambiguous. 

One issue I discuss with my students is how comedic controversies send two sacred liberal principles hurling toward each other in some sort of convulsing superconducting supercollider. One value is freedom of speech. The other is the demand that, for there to be peace, we all must extend toleration to people who aren’t like us. Chappelle either can’t figure out how to balance the latter with the former or is simply not interested in doing so.

Technology has irrevocably changed his art form. A quip made at Snickerz Comedy Club in Fort Wayne doesn’t stay in Fort Wayne anymore.

Dave Chappelle is, undoubtedly, a comic genius. But he’s not the only comic genius, and he’s one who, unlike many of his colleagues, hasn’t recognized that a different generation expects comedians to abide by certain rules. The first is: Don’t punch down. 

Chappelle can’t obey this dictum, because he embraces what scholars sometimes call a “standpoint epistemology.” Not without warrant, he regards his identity as an African American male as the most disparaged and degraded of identities. Hence, by definition, he is always punching up — even when his targets are other marginalized groups, be they Jews or transgender people or Asian Americans or white women or lesbians or gay men or whoever.

Another ground rule of today’s comedy that Chappelle disregards might be: Direct your most homicidally nasty bits at yourself or your own group. When dealing with your people: Give ’em the works.

The rule explains why Larry David’s infamous “SNL” monologue about flirting with a fellow female inmate in a Nazi concentration camp didn’t destroy his career (as it might have had, let’s say, Ali Wong or J.B. Smoove performed the bit verbatim). For better or for worse, this is a rule that most contemporary comedians understand. Were Chappelle to understand it, perhaps he would have pivoted to equally serrated humor about converts to Islam such as himself. Or maybe he’d make cracks about the odd entitlements and lifestyle choices of middle-aged male multi-millionaires who worked their way out of the middle class

A third concept that Chappelle needs to grasp is that technology has irrevocably changed his art form. A quip made at Snickerz Comedy Club in Fort Wayne doesn’t stay in Fort Wayne anymore. Within seconds, a joke can run astride the globe like a sneering, bullying colossus. Social media can radiate a tasteless barb to a million folks less intelligent than Mr. Chappelle. The joke might confirm their worst biases or spur their basest impulses. 

Until Chappelle reckons with the power of his medium or turns his relentless critical gaze on himself or genuinely tries a little tenderness, he’ll keep stoking the controversies he swears he wishes to avoid.