I think of all of this as I watch Chappelle, in a black hoodie, with his ever-present cigarette bungee-jumping from his mouth, pacing the outer ring of the Gotham Comedy Club in New York one night in March. The packed house has no idea he’s here, or that Jerry Seinfeld will introduce him. It is mostly white folks — 300 millennials, Gen Xers, baby boomers, shoulder to shoulder. The race of the crowd doesn’t matter to Chappelle. “I feel grateful that things are working out, the way people support me,” he had told me earlier. “It’s really warm, man, like an old friend. I was reflecting on it, and doing stand-up has been one of the most consistent parts of my life, you know what I mean? Like it was the first adult decision I made, and I really stuck to it.”
A colossal roar goes up when Seinfeld announces Gotham’s surprise guest. Chappelle arrives onstage to a standing ovation — the sort of wild applause generally reserved for, say, a populist presidential candidate, like Bernie Sanders or Donald Trump. Except Chappelle has a singular gift for blurring left and right, blue states and red states. His 11 years on the road have taken him from big cities to towns, allowing him to talk with, listen to and feel people, but with the sort of authentic interest a politician can rarely duplicate.
That Chappelle is an African-American raised by college professor parents, a Muslim with a Filipino wife, three biracial children and a white stepbrother, speaks to his singular ability to remix cultural boundaries in ways many cannot, or wish they could. He also happens to feel most comfortable in Middle America, on the acres of land he bought in Yellow Springs, Ohio, in the 2000s. So, yes, he is sprawling urban graffiti, with his casual usage of the N-word, his elastic black English and his fusillade of curse words, but he’s also small-town folk with a hard-won vulnerability.
I have known Chappelle and watched him do stand-up in New York since he was a bone-thin 19-year-old import from the Washington D.C. area, where he spent big chunks of his youth. Today, at 43, the baby face is gone, and there’s gray in his occasional goatee; his years of weight-lifting have yielded cartoonishly thick Popeye biceps. But what I see as I watch him pace that Gotham stage — freestyling on love, marriage, the ways and words of the LGBTQ community, racism, sexism — is a master at his…