Dave Chappelle’s Not Kidding: The comedian’s proposal to defer having his name on his high school’s theater might seem conciliatory. But it’s a big bet on what he believes.

The comedian Dave Chappelle returned to his hometown of Washington, D.C., Monday night—and to a painful controversy.

Chappelle is a graduate of—and generous donor to—Washington’s Duke Ellington School of the Arts. In 2017, the school completed an ambitious renovation. To express recognition and thanks to Chappelle, the school proposed to name its theater for him.

The naming ceremony had been scheduled for November 2021, shortly after the release of Chappelle’s Netflix special The Closer. That special featured a series of jokes about transgender claims. Notably, Chappelle insisted in blunt, earthy language on his view that gender, sex, and childbirth are biological facts. Those words triggered criticism and protests, including at Chappelle’s former high school. With Chappelle’s approval, the school delayed the naming ceremony.

The ceremony was rescheduled for Monday, June 20. The school sold tickets to the event as a fundraiser, and my wife and I bought a couple. The ceremony rules required all phones to be encased in a magnetically sealed folder, so I have no recording of the event, only personal recollection. The evening started with what looked like a show of force on Chappelle’s behalf by the school and its leading figures. The principal praised Chappelle. The chairman of the fundraising committee praised Chappelle. The jazz great Wynton Marsalis praised Chappelle. Via video from the Atlanta set of The Color Purple, the actor Corey Hawkins praised Chappelle.

Then, at last, Chappelle spoke, telling his own story of the Ellington school’s influence on his life, his fond memories of faculty and classmates. The narrative slowly built toward the controversy that erupted last November. Then came a surprise plot twist.

Chappelle proposed that the theater be named the Theater for Artistic Freedom and Expression, and then said that his name would be added later, only when and if the school community was ready.

It was quite a moment. The audience rapturously applauded.

As we walked into the soft Washington night after, two thoughts coalesced in my mind.

The first was admiration for the bravado and ingenuity of Chappelle’s maneuver. So often in these debates over free speech, the adversaries of expression claim to represent the wave of the future. Major surveys have found that Gen Z and Millennial Americans are much more willing to suppress speech in the name of equity than older Americans. Chappelle took a bet here, as if to say: Let’s see who will look silly in five years’ time, you or me.

The very act of bet-taking changes perceptions of the wager. The most powerful weapon of the adversaries of expression is their certainty. Chappelle wrenched that weapon from their hands, again as if to say: I am more certain even than you—and I’ve put a lot more of myself on the line.

As clever as the move is, it may be too clever. The second thought on the walk home was that Chappelle had defended his words by evading responsibility for them. Stand-up comedy is an art form, he’d said; it’s all about context and nuance. But if it is an art form, it’s an art form like poetry, one in which structure and content mutually reinforce each other but in which the content still matters.

A poem can work even if the reader rejects its ideas. You don’t have to agree that Christ died to redeem humanity to be moved by “The Battle Hymn of the Republic.” But you would not be moved by “The Battle Hymn” if Julia Ward Howe had not believed the words she wrote, if she’d thought they were just tinkling sounds. If comedy is art, it too depends on the artist’s belief.

The power of Chappelle’s art, if it is art, comes from forcing encounters with uncomfortable realities. Hence his famous gag about terrorists not taking Black people as hostages because “black people are bad bargaining chips.” Hence, too, his grim piece about Black Americans disregarding white Americans’ opioid crisis with the same haughty indifference as white Americans reacted to the crack crisis of the 1980s. “Hang in there, whites! Just say ‘No.’ What’s so hard about that?” If somebody claimed to be offended by those jokes, it would seem strange for the comic to defend them by saying “free expression” and stopping there.

“Free expression” protects our right to say things. But Chappelle’s performance on Monday night said more: The Closer was artistic expression, and it was great artistic expression.

Some critics, including at The Atlantic, did not enjoy The Closer. Its audience did skew male, but it also skewed huge, with nearly 400 million streamed minutes in the show’s first week on Netflix. Its millions of fans liked it because they heard something in Chappelle’s words that resonated with them, that expressed an aspect of the truth otherwise unheard. The Closer reveals his baseline of respect for sexual minorities, but Chappelle also complicated the story. And he complicated it by making comedy out of it.

Sigmund Freud observed that the psychological function of humor is to allow the expression of thoughts that formal society normally forbids. In American myth, the soldiers of World War II were heroes, the Greatest Generation. On The Phil Silvers Show of the 1950s, those soldiers were shown as lazy and venal. In sophisticated comedy, comedians play with the tension between formal and informal beliefs, and Chappelle’s is very sophisticated comedy.

The function of humor as a release from the forbidden thought explains why some of the most productive sources of jokes are authoritarian societies, because they forbid so much. In the squares of Moscow today, protesters physically reenact an old Soviet joke, demonstrating with blank signs because “Everybody already knows everything I want to say.” That same function of comedy explains why “woke America” is the target of so much satirical humor today, because so much of wokeness aspires to forbid.

When Chappelle deferred adding his name to the theater of the school to which he’d given so much of himself—not only checks, but return appearances—he was not yielding or apologizing. He was challenging the in-school critics: You don’t understand what I do—not my right to do it, but the reason it matters that I exercise that right. Until you do understand, you cannot have my name. Someday you will understand. You may have it then.

So what we heard in the new Duke Ellington School Theater for Artistic Freedom and Expression was neither a retreat nor an apology. It was a gesture of defiance, looking ahead to the time when the gesture will be redeemed. Chappelle to critics: The joke’s on you.