Dave Chappelle’s Freewheeling Podcast

When “Chappelle’s Show” first aired, in 2003, it was novel for its content and, more crucially, its attitude. The show had an effortless, laid-back cool, an unapologetic vulgarity, and a deep sense of mischief as Chappelle and his collaborators explored racial dynamics in America. But it also offered a critique of television as a form of entertainment. Most of the sketches parodied popular TV programs (“Frontline,” “The Real World”) or advertising tropes (QVC, car commercials), taking the ingrained rhythms of the medium and scrambling them. In one episode, there was a promotional clip for a fake show with the tagline: “It’s not HBO. It’s just regular-ass TV.” (“Chappelle’s Show” aired on Comedy Central, after being rejected by HBO.) Often, Chappelle would tell his live audience, in between sketch clips: “I can’t believe we haven’t been cancelled yet.” Now legendary for its rule-breaking spirit, “Chappelle’s Show” was absurdist television that brought to light just how absurd most other television was.

Nearly two decades later, Chappelle is tackling another format, bringing his rogue sensibility to the world of podcasting. Last month, he launched “The Midnight Miracle,” an understated, free-form audio show that bears no resemblance to the formulaic shapes that podcasts typically take, particularly those created by celebrities. Chappelle hosts the show alongside two of his oldest friends, the New York rappers Talib Kweli and Yasiin Bey (formerly known as Mos Def). In the early days of “Chappelle’s Show,” the two guested as Black Star, bringing an earnest and civic-minded hip-hop presence to the program. On “The Midnight Miracle,” Kweli and Bey have been promoted to colleagues and co-stars, and the show draws on decades of friendships and shared histories on the fringes of Hollywood for its stories.

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