Dave Chappelle, who turned 50 recently, climbed into a boxing ring of a center stage at the United Center on Wednesday. There were no ropes, no turnbuckles, no gloves. The Champ looked relaxed, cheerful, and wearing a loose sleeveless work shirt, strong. We know he’s the Champ — weight class: stand-up comedy, still performing — because he said so: He last toured with Chris Rock and Rock is the greatest, other than himself. He gets asked a lot about what he would have done if Will Smith tried to hit him, he said. He says he doesn’t know. But he has come to realize that he has been both men: He has been Will Smith, righteously, blindly vengeful, and he has been Chris Rock, knocked around.
He doesn’t say this to get a laugh.
Chappelle is more than two personas, and Wednesday’s sold-out United Center show found us facing yet another iteration of the comedian, and that’s bruised survivor.
Even if many of the blows were self-inflicted.
What made Chappelle so exciting on stage — and what made him so casually, thoughtfully, if not urgently, funny this time — was a lack of shtick. In the past he’s ended shows by having pancake dinners for audiences. He’s brought up Usher for impromptu concerts. He’s meandered, contradicted. His stories could be short, but more often were long and stripped of belly laughs. He told a fantastic one at the United Center about running into Lil Nas X and realizing this artist is living a very specific dream. It led to a story about a teacher asking students about their dream jobs someday. Fireman, one says (but, as Chappelle continues, this dream gets very dark). President of the United States, replies another (which Chappelle spins into a job at Walmart and early death).
Yet Lil Nas X — a Black LGBTQ rapper, country twinge — knew exactly what he would be, Chappelle said. The comedian said it with clear admiration and a hint of atonement.
Indeed, a couple of years ago, his Netflix concert film “The Closer” brought Chappelle as close to canceled as one can get and still, less than two years later, he sold out the United Center (and has two more mostly sold-out shows Friday and Saturday). He painted transgender people then with broad strokes and pandered with cheap shots — and rightfully caught hell. He ended the special by saying he was done with the subject, but in Chicago, he brought it up often — usually to say he was done discussing it, again.
This new arena tour feels designed to turn the page on the rank ugliness. It’s called “It’s a Celebration!” and there’s a DJ to hype up the audience with Whitney Houston and Bell Biv DeVoe. Everyone gets a free Chappelle tote bag at the door (random, but OK). And the first of the four opening standup comics is Flame Monroe, a brassy transgender comic who grew up in the Henry Horner Homes near the United Center and, in closing her set, notes that she stands with Chappelle. But Chappelle himself wants to reassure that he will still step over a line or two. He hasn’t been totally scared straight. At one point he even said he can still say anything he wants — as if, despite playing 23,000-seat arenas and making Netflix specials, you’re wondering. If he ended with a Sinatra-esque “My Way” of bombastic defiance, it wouldn’t have been out of place. The whole thing — particularly Chappelle’s drift toward self-aggrandizement — would come off hacky if Chappelle wasn’t also surprising. At his worse, he steps over a line, the audience gasps and the joke feels almost incidental to the shock. More often, he’s patient, personal and incisive.
But you have to wait. It’s whiplash, in other words, to have him open with intentionally offensive bits on the homeless and why he’s only picking on the disabled now, then score pandering points on reproductive rights, then veer into a smart, observant memory of running into retired boxer Floyd Mayweather because the former champion works the cash register at his strip club in Las Vegas and, incidentally, Chappelle likes to go to strip clubs alone, which his wife thinks is weird — “Do you think it’s weird?”
He leaned forward and asked someone, as if he sincerely wanted to know.
Remember, here is a guy who once rejected the audience itself, abandoned his hit comedy sketch show and wondered if his work was irresponsible. Few standups are so present, so plainly sensitive to how they’re being received. On stage, Chappelle smokes most of a pack. He says some stories are true (but doesn’t specify). He responds to shouting idiots. He muses on those who get “drunk off the feeling of being right,” but stops short of implicating himself. It’s hard to say when he is evading or digging in. The comedy of Dave Chappelle is live diary-making, full of blind spots, dumb thoughts and confusion. It’s hard to ask questions about what you don’t understand, and Chappelle, when he’s on, captures a tension between knowing better and not knowing enough. He may say he’s done talking about some subjects, but his brain is saying something else.