Unfunny Brilliance in Standup Comedy: Part 2, Dave Chappelle

Comedian Dave Chappelle released four standup specials in 2017 that are considered his return to show business, after quitting Chappelle’s Show in 2006. The way he suddenly left the successful show (and a $50 million contract with Comedy Central) led to rumors he had a drug problem or mental health issues. Chappelle has hinted in interviews that the real problem was maintaining his integrity working with the network, though he has never been specific.

He has changed, of course, over that decade. The most obvious aspect is his physical appearance. He has said he started working out to relieve stress and is now much bigger than the lanky, loose physical comedian he was back then. When he made an appearance at the 2016 NBA Finals, social media went crazy over how muscular he had become. “Dave Chappelle looks like he ate a younger Dave Chappelle,” one person tweeted.

More importantly, he looks mature, less jittery. His face looks fatigued and a little sad, but he seems more rooted, ready to stay put, physically and intellectually.

In The Age of Spin he talks about his four encounters with OJ Simpson and his childhood admiration for Bill Cosby. Deep in the Heart of Texas is less structured and shows some of his younger reliance on the topic of sex. Both of these won a Grammy.

With Equanimity, he seems on the verge of what comes next. Comedy may not be it.

“But you know why I be thinking sometimes I want to stop doing comedy?” he says in Equanimity. “I don’t want to sound like a braggart saying this, but the real reason I want to stop is because I’m too goddamn good at it … I’m not even exaggerating. It’s not exciting. Every night before I come out on stage, I’ll be backstage, like, ‘I’m sure this is gonna go well.’ And it always does.”

This self-referential nod is followed by analysis of his fans’ reactions to a subject he refuses to drop, and the nature of comedy itself. (“I mean, it’s funny if it’s not happening to you,” he says.) He talks a long time about Trump and manages to be funny and persuasive.

The last eight minutes of the show, however, swerve from comedy into storytelling with nothing funny in them.

“Picture, it’s the early ’50s in the United States,” Chappelle says. “This 14-year old boy goes down from Chicago to Mississippi….” It sounds like the setup to a joke, but of course the boy is Emmett Till. Chappelle calmly and movingly tells the story of Till’s murder and mutilation. “And if our civil rights movement was a car,” Chappelle says, “this boy’s dead body was premium gas. This was a very definitive moment in American history, where every thinking and feeling person was, like, [noise of disgust], ‘We gotta do better than this.’”

He connects Carolyn Donham’s lie about Till, which led to his lynching, to the civil rights movement “that made my wonderful life possible. That made this very night possible.”

“How could this be, that this lie could make the world a better place? It’s maddening,” he says. The totality of it is, he says, “humbling.” When he ends the show a moment later, he reverts to an adolescent punch-line he has used throughout. The line was never funny and is further diminished in relation to the Till material. This may not be a misstep, however, but a consequence of working comedy from one mastery into what comes next.

The first three specials were filmed in big auditoriums. The fourth, The Bird Revelation, was shot in a small club and is only a 48-minute set. Chappelle’s topics include sexual harassment, Black Codes, Jim Crow, and the “brittle spirit” of our age. There is philosophizing, lecture, and more than a hint of defensiveness (about Me Too). The last 17 minutes are a strange, unfunny summary of the book Pimp, by Iceberg Slim, as it seems to apply (in Chappelle’s mind) to his own relationship with Hollywood.

In Bird, Chappelle reworks his idea on the nature of comedy from Equanimity. This time he says, “And everything’s funny ‘til it happens to you.” The problem of comedy in the current climate, he seems to say in these specials, is that everything touches everyone now, so we struggle for a new form.