I’m still crossing the line

Dave Chappelle, who recently turned 50, climbed into the boxing ring at center stage at the United Center on Wednesday. There were no ropes, no turnbuckles, no gloves. The champion looked relaxed, cheerful, and wearing a loose, sleeveless work shirt, strong. We know he’s the Champion – in his weight class: stand-up comedy, still performing – because he said so: He last toured with Chris Rock, and Rock is the best other than himself. He gets asked a lot about what he would do if Will Smith tried to shoot hesaid. He says he doesn’t know. But he realized it was both men: He was the righteous, blindly vengeful Will Smith, and she was Chris Rock, who was just wandering around.

He’s not saying this for laughs.

Chappelle is more than two personalities, and Wednesday’s sold-out United Center show found us face to face with another version of the comedian, and this one is the injured survivor.

Even though most of the coups were self-inflicted.

What made Chappelle so exciting onstage — and what made him so casually, thoughtfully, unurgently funny this time around — was his lack of bullshit. In the past, he has ended shows by serving pancake dinners to the audience. He trained Usher for impromptu concerts. Convoluted, contradictory. Their stories may have been short but they were more LONG and belly-free laughter. He told a great story about running into Lil Nas X at the United Center and realizing this artist was alive. a very special dream. This led to a story about a teacher asking students about their dream jobs one day. Fireman, someone says (but as Chappelle continues, this dream gets darker). The President of the United States gives another answer (Chapelle turns this into a job at Walmart and an early death).

But Chappelle said Lil Nas X, a black LGBTQ rapper and country rapper, knew exactly what was coming. The comedian said this with clear admiration and a hint of regret.

Indeed, a few years ago the Netflix concert movie “The Closer” brought Chappelle as close to cancellation as he could get, and yet, less than two years later, he sold out the United Center (and has two other movies that are mostly sold out). indicates Friday and Saturday). At the time, he portrayed transgender people in broad strokes and pandered to cheap shots, and he rightfully got hell. He ended the special by saying he was done with the topic, but he brought it up frequently in Chicago — usually to say he was done discussing it again.

This new arena tour seems designed to turn a new page on the ugliness of the rankings. It’s called “It’s a Celebration!” and there’s a DJ to thrill the crowd with Whitney Houston and Bell Biv DeVoe. Everyone gets a free Chappelle bag at the door (random but okay). And the first of the opening four stand-up comics is Flame Monroe, the sassy transgender comedian who grew up in the Henry Horner Homes near the United Center, and he notes that Chappelle is by his side as he closes his set. But Chappelle himself wants to reassure that he will still cross a line or two. He wasn’t completely frightened directly. At one point he even said he could still say whatever he wanted; It’s like you wonder about this, even though he plays in halls with 23,000 people and makes Netflix specials. It wouldn’t have been out of place if he’d ended with a Sinatra-like “My Way” of over-the-top defiance. The whole thing, especially Chappelle’s turn to self-aggrandizement, might feel contrived if Chappelle weren’t startling, too. Worse, it crosses a line, the audience gasps, and the joke feels almost incidental in the face of shock. He is often patient, personal and insightful.

But you must wait. In other words, it’s a big blow for him to say deliberately offensive things towards the homeless and why he’s only now turning to disabled people, then get fawning points on reproductive rights. Later We flash back to a clever, careful memory of encountering retired boxer Floyd Mayweather because the former champ was working the cash register at a strip club in Las Vegas and, coincidentally, Chappelle liked to go to strip clubs alone, which his wife thought was weird – “You think that’s weird?”

He leaned forward and asked someone as if he really wanted to know.

Remember, here is a man who once rejected an audience, left his hit comedy sketch show, and wondered if his work was irresponsible. Very few standups are like that To present, they are clearly very sensitive about how they are received. Chappelle smokes most of the pack on stage. He says (but does not specify) that some of the stories are true. He answers to the shouting idiots. He muses about those who are “drunk with the feeling of being right” but stop short of involving themselves. It’s hard to tell when he’s running away or digging. Dave Chappelle’s comedy is full of lively journaling, blind spots, silly thoughts, and confusion. It’s hard to ask questions about things you don’t understand, and when Chappelle is on, he captures the tension between knowing better and not knowing enough. He may say he’s done talking about some topics, but his brain is saying something else.

cborrelli@chicagotribune.com