The New York Times Ran an Excellent Piece on the Sort of Comeback of Dave Chapelle
He's gotten a bit darker:
His characteristic laid-back delivery and pinpoint timing were in service of jokes that were more dark, intricate and revelatory than his stand-up from a decade ago. Seeing Mr. Chappelle evolve onstage was a reminder that he didn’t leave comedy so much as return home to the live form he has practiced for a quarter-century. Mr. Chappelle might have left television, but that departure has become the wellspring of his comedy now. He only needs a microphone and a stage to lay claim to greatness.
When Mr. Chappelle walked onstage for the first of two shows in Richmond, Va., in June, he appeared frazzled. “I almost didn’t make it,” he said, explaining that he showed up at the airport before buying a ticket. “I didn’t plan,” he said, adding that he “used to have people” do that. “Now, not as many people do.”
He's not shying away from his past
What’s changed since that special is that his jokes now always seem to circle back to his infamous exit from Comedy Central, explicitly or, more often, implicitly. For instance, Mr. Chappelle acts out a joke that comes off like an elaborate multi-act play about how his son, following his advice, left an after-school program he didn’t like. “Son, sometimes, it’s O.K. to quit,” was the title he coined for his parental lecture.
This counsel has unintended results when his son’s classmate also quits, upsetting his father, a Roman Catholic named O’Malley worried about Mr. Chappelle’s influence. He confronts the comic at school one morning saying: “O’Malleys don’t quit.” Taking cartoonish umbrage, Mr. Chappelle responded with alacrity: “Well, Chappelles do.”
He's still trying to figure it all out:
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.
Go read the full article over at the New York Times.