To think, the audience here could’ve gotten some of this:
An epic 10-minute story about a charged exchange with a homeless man he meets outside his upscale Manhattan hotel had the poetic weight of an August Wilson monologue. Since San Francisco, this morally engaged story has become more ornate and moody, the jokes emerging from meticulously sketched vignettes.
Mr. Chappelle explicates the story’s emotional shifts mostly by describing the homeless man’s eyes. At first, he sees “recognition, pleading, a glimmer of hope.” Mr. Chappelle slows his voice down, enunciating, stopping his comic momentum to linger on an image. Then he pauses and, out of nowhere, yells at the man — “You stink!” — then returns to his eyes, which are “angry,” revealing a “spirit broken.”
Mr. Chappelle then flees the scene. “Instantly,” he said, “I … felt … better about my problems,” he says, to huge laughs.
In these shows, Mr. Chappelle describes lashing out or quitting as a wonderful relief — at first. Then come the repercussions. After escaping the homeless man, Mr. Chappelle feels regret upon seeing his reflection in a door. He realizes he shouldn’t have insulted the man and left. When he asks for forgiveness, the homeless man accepts in a voice that seems surprisingly confident and authoritative, a gravelly, baritone telegraphing virtue. Mr. Chappelle, who has been shopping and eating at posh spots, gives the man a gift: A Sean John sweatsuit. (On “Chappelle’s Show,” Puff Daddy — now Diddy — who owns Sean John, was portrayed as pure show-business decadence.)
The homeless story is about a rich but unhappy Chappelle panicking and running away, but one that explains the context of his actions. He was unhappy, in a confused state of mind, taking advantage of his wealth and fame. After returning, he sees he has mistreated the homeless man. But he ends on a slightly cynical twist since even the dignified-sounding homeless man gets excited when he sees the Sean John outfit.