A few months ago, a good friend of mine invited me to see Dave Chappelle perform in Yellow Springs, a small town in Ohio known for its charm, progressive vibe, and, increasingly, as a kind of creative refuge for one of the most influential comedians of our time. The show was about an hour north of Cincinnati, not too far from home. But I declined.
It wasn’t a scheduling conflict or a lack of interest in live comedy. On the contrary, I’ve long admired Chappelle’s talent. He’s a masterful storyteller with a razor-sharp mind and a sense of timing that most comedians could only dream of. But as I weighed the decision to go, I kept returning to a familiar feeling—a quiet discomfort that’s been growing over the years. I wasn’t afraid of being offended. I was afraid of being complicit.
Comedy, at its best, is a mirror. It reflects society back at itself—sometimes funhouse-distorted, sometimes uncomfortably accurate, always revealing. Chappelle has historically wielded that mirror better than most. His early work on Chappelle’s Show was nothing short of revolutionary: irreverent, fearless, and painfully funny. But as the years have passed, the reflection has grown murkier. The mirror now seems to distort some faces more than others.
I first began to feel uneasy during Chappelle’s early rise to fame. Back when his sketches tackled race in America with both brilliance and boldness, there was an undercurrent I couldn’t ignore. As a Black man, I understood the nuances of what he was doing—satirizing racism, holding it up for scrutiny. But when I watched white audience members laugh—sometimes a little too loudly, a little too comfortably—I wondered: Do they get the joke, or are they laughing at it for the wrong reasons?
Chappelle himself seemed to notice the same thing. In one of the most widely discussed moments of his career, he walked away from a $50 million contract and his hit show on Comedy Central because he realized something chilling—people weren’t always laughing with him; they were laughing at the very people he was trying to humanize. In his words, they were laughing “for the wrong reasons.” That decision, and the integrity behind it, is one of the reasons I’ve respected him for so long.
But in recent years, something has shifted.
Over the last several stand-up specials, Chappelle has turned his attention toward a different community—transgender people, and more broadly, the LGBTQ+ community. His jokes on this subject have been the focus of widespread criticism, as well as staunch defense. Chappelle insists that he’s not “punching down,” that he’s merely telling the truth as he sees it. And again, many people laugh.
But here’s the thing: the laughter sounds familiar.
It sounds like the same uncomfortable laughter I heard years ago, when his sketches about Black stereotypes were met with howls of approval from people who, I suspected, weren’t quite in on the joke. Except now, the laughter is directed at a community already under siege—targeted by politicians, mocked by media figures, misunderstood by the general public, and fighting every day for the right to simply exist as themselves.
As someone who believes in the power of comedy to challenge, provoke, and yes, offend, I don’t believe in silencing comedians. I believe in critique. I believe in asking better questions—of ourselves and of the people we admire. And one question I can’t shake is this: When we laugh, who’s hurting?
The golden rule of comedy has long been this: punch up. Take aim at the powerful, the hypocritical, the corrupt. Shine a spotlight where others fear to look. The best comedians, from Richard Pryor to George Carlin to Hannah Gadsby, have used their platforms to disrupt the status quo, not reinforce it.
When comedians punch down—when they mock people who are already marginalized—they risk becoming part of the machinery of exclusion, even if unintentionally. And in today’s world, where transgender people face disproportionate levels of violence, discrimination, and erasure, the damage done by a high-profile joke can be deeply consequential.
It’s not about being “too sensitive” or “cancel culture.” It’s about context. Comedy doesn’t exist in a vacuum. It reverberates through our culture, echoing in locker rooms, classrooms, dinner tables, and state legislatures. When someone as influential as Dave Chappelle uses his platform to repeatedly frame transgender people as the butt of the joke, it sends a message—whether he means it or not.
And the message is this: They don’t matter as much.
One of the most common defenses I hear in conversations about Chappelle’s more controversial material is that he’s just telling “the truth.” He’s saying what others are too afraid to say. But truth without empathy can become cruelty. And when your truth dismisses or diminishes the truth of others—especially those who live at the margins—it stops being courageous and starts being callous.
People often forget that there is more than one truth in the room. A comedian’s truth is not the only truth. For a transgender person navigating a world that questions their identity, their safety, and their very humanity, the truth looks different. And their truth deserves as much room, respect, and reflection as anyone else’s.
There is a difference between telling jokes about people and telling jokes at people. The former requires curiosity and compassion. The latter requires neither.
Whether he likes it or not, Dave Chappelle is a cultural bellwether. What he says matters—not just because he’s famous, but because he’s good. His words carry weight. And that weight lands differently depending on who’s listening.
I’ve spoken to friends—Black, white, gay, straight, cis, trans—who find his latest material hilarious. I’ve also spoken to many who feel betrayed, unseen, and hurt by it. Both responses are valid. Art hits differently depending on where you stand. But the discomfort I feel isn’t about disagreement. It’s about seeing who gets empowered by the punchlines.
When a comedian’s work is cited by bigots to justify their own prejudice, something has gone wrong. When people laugh not in spite of a group’s marginalization but because of it, something has gone terribly wrong.
It’s not Chappelle’s job to appease everyone. But it is his responsibility—as it is for anyone with a platform—to consider the ripple effects of what he puts into the world.
Declining the invitation to that show in Yellow Springs wasn’t a protest. It wasn’t a statement. It was simply a choice based on values. I can admire Chappelle’s genius while still choosing not to support the aspects of his work that cause harm. That’s not “canceling” someone—it’s exercising discernment.
Too often, we treat celebrities like they can only be one thing: either completely worthy of adoration or completely irredeemable. But people are complex. Chappelle is complex. He’s not a villain. He’s an artist—a brilliant one—who, like all of us, is capable of both insight and oversight.
It’s possible to hold space for both truths: that he’s one of the greatest comedians of our generation, and that his recent work contributes to a culture that makes life harder for people who already have to fight for dignity.
In the end, this conversation is about more than comedy. It’s about what we’re willing to laugh at, and what that laughter says about who we are. It’s about empathy, responsibility, and the courage to confront the consequences of our choices—even the ones that seem as small as buying a ticket or streaming a special.
I didn’t go to the show. And while I don’t expect everyone to make the same decision, I do hope we all take a moment to ask ourselves: When we laugh, who’s hurting? And are we okay with that?
Because the answer to that question says more about us than any comedian ever could.
