Dave Chappelle Opens Up Like Never Before On Letterman's Netflix Show

Dave Chappelle is most famous for his early ’00s sketch show, Chappelle’s Show. Even more famous than the show itself is the way he abruptly chose to end it. And for years, people continued to speculate on what would make him walk away from such a huge opportunity. He’s spoken about his decision in recent years as he began his comeback, but his recent appearance on David Letterman’s Netflix show is the first time he’s spoken candidly about what exactly led to him walking away. He also speaks about being a Black creative and Black man in America right now.

In short, a member of his crew laughed at the wrong part of a racially charged joke. He admits that the laugh sent him on a path of wondering what the hell he was doing. “It just raised an interesting question to me, which I was already wrestling with in the first place,” Chappelle explains. “There’s instances where you do go too far. You’re playing with powerful shit, doing jokes about racism, and this -ism and that -ism. To me, I looked at it as an occupational hazard, but I also realized that I was bigger than I was comfortable with.”

In the sketch, Chappelle explains that he was dressed in blackface and he’d pop up whenever someone felt the pains of racism. If executed properly, the sketch could have been a hilarious commentary of how commonplace racism is in the country. But because the person laughed at a place that isn’t the joke, it hit different. “It’s not a bad sketch. But hearing the wrong laugh while you’re dressed that way, it makes you feel shame,” he said.

For marginalized creatives, there’s always a line you have to straddle. How much self-deprecation is too much? When does your comedy cross the line from being a social commentary to giving too many people permission to laugh at you? Chappelle, like many Black comics of his generation, knows how to turn the mirror on his white audiences. But it’s clear that he also knows what happens when you give white audiences too much of you. They will think they have a pass to be on your side of the joke.

Like other Black creatives, he knew he had to walk away while he still had the space to do so. But he also understood the huge risk he was taking by doing what felt right. When you walk away from that kind of status with white audiences, you don’t always know if it’s going to be there when you come back. And that was something he had to grapple with. But ultimately, he began to find peace with his decision. Because it led him to really re-examining his work and taking a more critical look at the state of the world.

In the last couple years, Chappelle has rightfully come under fire for his criticisms of “cancel culture.” All three of his Netflix standup specials have been called out for his transphobic comments. In the most recent, Sticks & Stones, he directly confronts the criticisms of his previous specials. He doubles down on his feelings on cancel culture, defending friends Louis CK and Kevin Hart, and mocking survivors of sexual assault. He also calls himself out for the way he constantly jokes about the trans community, but continues to do it. In his interview with Letterman, he calls it a “well-intentioned piece.”

While taking Letterman on a tour of his home city, he explains that “Gays are welcome. All the letters of the alphabet are welcome in Yellow Springs.” So it begs a question that Letterman doesn’t ask. If Chappelle lives by the ethical credo of “kindness” set by his hometown, why does his work eschew that decency? Does he genuinely enjoy mocking the transgender community, or does he simply make those jokes to keep his fan base happy? That’s an answer we don’t get in this conversation.

As we can expect since the interview was conducted fairly recently, Letterman asks Chappelle about the state of the country right now. Chappelle is a Muslim, and Letterman asks him how he feels about the president’s desire for a Muslim ban. Because Dave Chappelle is a Black man in the country with a modicum of sense, he takes the question in stride. “You don’t expect necessarily that much empathy or compassion or cultural astuteness from a guy like that,” he explains. He goes on to point out that Biden’s indictment of Trump being the first racist president is untrue, which is just common sense at this point. “So how do I feel when I hear a white person say some stupid shit?” he asks. He shrugs it off with a laugh.

The sweetest moment during the conversation is when Dave Chappelle talks about his children. He has three, two sons and one daughter. “The new models are better than the old models, you know?” he asks Letterman when talking about them. He gives much of the credit for raising them to his wife, who he admits did a lot of the heavy lifting when his sons were younger and he was doing Chappelle’s Show and traveling to do stand-up. “Mother is the word for God in the hearts and lips of children,” he says. Much like a dad, his end game with his kids when they were young was to remind them that he was the “coolest motherfucker you will ever meet.” But he does go on to say that he really tries to reinforce that they can trust him.

Dave Chappelle is a Black man with a lot of brilliant things to say on the subject. But as we learn in this interview, he’s incredibly self aware. And for the most part, his comedy reflects that awareness. However, even he admits that he’s just one guy. He’s not perfect, and the trappings of celebrity aren’t important to him. He just wants to do what he loves.

My Next Guest Needs No Introduction is now streaming on Netflix.