On Tuesday night, Dave Chappelle visited Late Show with David Letterman to promote a series of standup gigs he's doing at Radio City Music Hall next week, and the comedian's ensuing chat with Letterman marked his first late-night television appearance since he dropped by Late Night with Conan O'Brien in 2008 (as well as his first appearance on the Late Show in a decade).
As you may expect, the topic of Chappelle's 2005 exit from his extremely popular Comedy Central series Chappelle's Show came up. There were plenty of highlights; the two Daves calmly discussed why Chappelle left and whether he regrets the decision (among other things), with Chappelle pointing out that "technically, I never quit—I'm seven years late for work."
Check out the edited version of the interview below to see all the best Chappelle's Show-related bits, or the full 14-minute conversation below that to hear Chappelle weigh in on fatherhood, performing standup, what it means to have money, and more. If you've got the time, I highly recommend settling in for the extended chat—the guy's got some really intelligent and even inspiring things to say.
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Season 3 : Episode 4