Chappelle vowed to be hitting pause on jokes about the LGBTQ+ community until he and the LGBTQ+ community could both be laughing together again. "I'm telling you: It's done. I'm done talking about it," he concluded.
But on Monday night, Chappelle laughed as he acknowledged his promise to stop with that kind of material, but with the new caveat that he'd only do so if the set was being recorded, earlier pointing out that everyone in the 20,000-person arena had their cellphones locked away in Yondr pouches.
After the screening of his heartwarming documentary, it took Chappelle only a few seconds to launch headfirst into his recent troubles. "Week four of being cancelled, it's crazy," he began, launching into a tale about how he had to take out an order of protection against a racist neighbor who had turned up at his house a few months ago.
He described that his wife had gifted him a pearl-handled .22 caliber pistol, joking that the last thing someone would say to him before he had to use the weapon would be "f----t." And if Chappelle did end up going to jail for murder, to escape the roughness of prison he said he would simply claim to identify as a woman.
Chappelle continued with his bit, explaining that after getting the order of protection against his neighbor, he offered to pay for his rehab or therapy, because clearly the man was not mentally well.
He said the payment would have to be kept a secret, otherwise other people with no health insurance would come knocking on his door looking for medical help, adding that trans people would be among those asking him to pay for their surgeries.
Chappelle went on to boast that he's glad he wasn't technically cancelled, saying he was lucky that he had been surrounded by a circle of friends, later bringing out comedian Jon Stewart, as well as musicians Fat Joe, Busta Rhymes, and Rakim.
He also made a series of pronoun jokes. When introducing the musician H.E.R., he quipped, "It's a pronoun you don't hear much!" Later on when riffing with Stewart, Chappelle mentioned that he'd form a transgender tribute band named "They."
Stewart, who had just professed Chappelle's graciousness and blasted people who wanted to make money off conflict, seemed to shrug the jokes off, adding "Can't stop, won't stop," toward Chappelle's line of jokes.
