Dave Chappelle’s Freewheeling Podcast | The New Yorker
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.
Although there is plenty of conversation, “The Midnight Miracle” is not a talk-radio-style podcast, nor is it a narrative show. There is none of the traditional scaffolding that we’re accustomed to on podcasts—Chappelle does not bother with overly formal preludes, introductions, or signposts. Instead, “The Midnight Miracle” drifts from story to story, fading hazily in and out of carefully selected musical interludes. (Each episode is a testament to his love of music, and will also be released on vinyl.) The show treats podcasting like an opportunity to make experimental art. Unlike “Chappelle’s Show,” “The Midnight Miracle” doesn’t explicitly critique the traditional constraints or tropes of the form; instead, it has a blue-skies sensibility that simply sidesteps the customary practices of podcasting altogether. I wouldn’t be surprised to learn that Chappelle had never listened to a podcast before recording his own.
In one episode, Bey recalls one of Chappelle’s marathon six-hour standup shows from decades ago. Bey had snacked on a cookie backstage beforehand. Chappelle, during his set, called on Bey to entertain his audience while he took a bathroom break. It was only as Bey stood in front of the crowd that he realized what he’d consumed. “Why am I this relaxed? I’m still Black in America. . . . What’s going on?” Bey recalls. “Then I realized . . . I’m high.” Just as Bey began to make the connection between the cookie and his altered state, Robin Williams joined the stage for a surprise guest set, at which point the two-hundred-and-twenty-seat theatre sounded “like ten thousand,” Chappelle remembers. “At the end of the night, it was me, Mos, and Robin onstage killing it, just like we’re doing now.” Williams ended up trying to rap alongside Bey. These are the types of stories that are the bread and butter of “The Midnight Miracle,” a show heavy on misty-eyed reminiscence.
Not all of these tales have such levity, though. The same episode contains a floaty piece about death called “How to Inspire,” in which “How do you keep a despondent person alive?” Bey asks. “How do you make somebody want to live? Is there a thing that you can even do for someone like that? Seriously.” Bey is inspired to tell a story about his friend, the late singer Amy Winehouse, and the experience of being in her midst when she was using heavily. He extolls the benefits of being kind and nonjudgmental to people in anguish. Still, the episode resists tidy conclusions, instead languishing in a contemplative, quasi-mystical space: “The fact of the matter is that we’re all walking in the same direction. It’s how you get there that matters most,” Bey says. Tonally and structurally, the show makes for an absorbing, psychedelic listening experience that feels both half-baked and meticulously wrought, and blissfully light on grievance-airing.
Since his return from hibernation, Chappelle has drifted away from the role of the pure standup, taking on the air of an orator or public intellectual in his specials. Sometimes his sets have the feel of extremely entertaining lectures. These days, he often has a bemused but curmudgeonly attitude, professing his disdain for what he perceives is a culture of censorship, although he’s usually too savvy to use terminology like “cancel culture.” He often defends standup as a sanctuary for free thought, and argues that it should be immune to censorious cultural forces. These sentiments have earned him plenty of criticism, and they also tend to make him sound stubbornly out of touch. In one special, from 2017, he went on a generic tirade in which he lamented, “Everything you say upsets somebody,” sounding more like a paranoid member of the élite defending his perch than a provocateur or a keen-eyed comic examining new fissures in society. And his nagging fears about censorship have not exactly borne out: his 2019 special “Sticks and Stones,” during which he chastised Louis C.K.’s accusers for “ruining . . . [his] life” and wrote off gender dysphoria as “a hilarious predicament,” won him two Emmys.
But there’s another undercurrent that has emerged in Chappelle’s comedy that is subtler and more easily overlooked. Recently, he has also seemed softer and more full of wonder. Just as Chappelle has been an advocate for self-expression, he is also a champion of human experience, and the idea that people should remain open to life—to strive to “make memories,” as he likes to say. When Chappelle received the Mark Twain Prize for American Humor last year, Aziz Ansari told a story at the ceremony, which was later aired on Netflix, about Chappelle’s urging him to eat some magic mushrooms after a show. Chappelle argued that, in twenty years, tripping on psychedelics would make for a far better story than “You got some sleep.” “I said, ‘Dave, you’ve got a point. Let’s eat those mushrooms,’ ” Ansari told the audience.
Chappelle has carried this memory-making—and hallucinogen-loving—sensibility through the pandemic, during which he frequently hosted live, outdoor comedy shows on his land in Ohio, flying out comedians to perform and carouse together, and occasionally go on kayaking trips. (He reportedly hired a chef designated to make food and drink out of cannabis and psychedelics, and both Chris Rock and Tiffany Haddish have told stories about being under the influence at these now-infamous gatherings.) During lockdown, he also recorded and filmed constantly—a practice that surely yielded the material and inspiration for “The Midnight Miracle.” The podcast makes you feel like you’re eavesdropping on intimate conversations inside a beloved celebrity’s home. The form also allows Chappelle to blend storytelling, insight, and provocation more subtly than in the standup format. In a recent episode that features David Letterman, Bey launches into a story about a time he refereed a “midget boxing match” in Manila. Chappelle interrupts with an edit: “Quick note from the editor: what happens next is a series of very unfortunate phrases that ultimately made David Letterman leave.” Rather than play the entire conversation, Chappelle presents brief snippets set to music, leaving most of the objectionable story to the listener’s imagination.
In another episode, he tells the story of being a young comic, high on mushrooms and riding a horse and buggy around Manhattan with his then girlfriend (now wife). He pulled up to a comedy club for an impromptu set. He was reminded of this day recently, Chappelle explains, when he received a Polaroid picture of himself and his wife in the mail. A stranger had found it in a car and tracked his wife down on Instagram to send it to him. It was taken on the day of the magic mushrooms and horse and buggy. In this story, Chappelle gracefully expounds on the idea that magic lurks around every corner if you leave yourself available to it. “I’m trying to tell you,” he concludes, “We never know if it’s going to be the time that we’ll make the memory that we never forget.”