Dave Chappelle and Saturday Night Live have a relationship that’s basically become a national barometer. Every few years, things get tense in America, and Lorne Michaels picks up the phone. It’s a pattern now. 2016. 2020. 2022. And most recently, his fourth stint in January 2025.
People don't just watch Dave Chappelle SNL skits for the laughs. They watch to see if he's going to say the thing you aren't supposed to say. Honestly, he usually does. Whether it's the post-election tension or the fallout from his own Netflix controversies, Chappelle uses the Studio 8H stage differently than any other host. He doesn't just play characters; he highjacks the cultural conversation for 90 minutes.
The Resurrection of Chappelle’s Show Characters
When Dave first hosted in November 2016, the air was heavy. Trump had just won, and half the country was in shock. Most hosts would have played it safe with a "we'll get through this" monologue. Dave went the other way. He gave us a Walking Dead parody that brought back the ghosts of Comedy Central past.
Seeing Clayton Bigsby in a "Make America Great Again" hat was jarring. It was brilliant. He didn't just do a "greatest hits" reel. He used Tyrone Biggums, Silky Johnston, and Lil Jon to comment on a brand-new political reality.
- Tyrone Biggums: The crack-addict character who somehow survived a Negan-style execution because his neck was too "ashy" for the bat to grip.
- Clayton Bigsby: The blind black white supremacist who finally felt he belonged in the new political climate.
- Silky Johnston: The legendary "Player Hater" who brought his vitriol to the zombie apocalypse.
This wasn't just nostalgia. It was a bridge. He was taking the 2003 version of himself and forcing it to look at 2016. It worked because it felt dangerous. You weren't sure if he was allowed to bring those characters back, especially to a network like NBC.
The Potato Hole and Biting Satire
Fast forward to 2022. The 2025 hosting gig hadn't happened yet, and the world was arguing about Dave's stance on various social issues. He walked onto the set and did a sketch called "Potato Hole."
On the surface, it’s a silly bit about a blues musician named Willie T. Hawkins (played by Chappelle) promoting an album with a weird name. The morning show anchors, played by Heidi Gardner and Andrew Dismukes, keep giggling at the phrase "Potato Hole." They make it a dirty joke. They make it light.
Then Dave drops the hammer.
He explains that a potato hole was where enslaved people hid their meager belongings—and sometimes themselves—to survive. The laughter in the room stopped. That’s the Chappelle specialty. He lures you in with a "low-brow" joke and then hits you with a history lesson that makes you feel like an idiot for laughing. It was a direct reference to the real-life musician Booker T. Jones and his 2009 album of the same name.
The Monologue as a Weapon
You can’t talk about Dave Chappelle SNL skits without talking about the monologues. They aren't five-minute sets. They’re 15-minute manifestos.
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In 2022, his monologue focused heavily on Kanye West and Kyrie Irving. He spent a massive chunk of time dissecting the "rules" of Hollywood. He famously read a prepared statement: "I denounce antisemitism in all its forms and I stand with my friends in the Jewish community." Then he paused and said, "And that, Kanye, is how you buy yourself some time."
It was a masterclass in tension. The Anti-Defamation League (ADL) wasn't happy. CEO Jonathan Greenblatt said it "normalized" antisemitism. On the other hand, comedians like Jerry Seinfeld found it complex, even if they didn't agree with every beat. Chappelle doesn't care about the consensus. He wants the friction.
Why the 2025 Hosting Gig Mattered
By the time Dave returned on January 18, 2025, with musical guest GloRilla, the vibe had shifted again. This was his fourth time. He had become a "tradition" host. The sketches this time around felt less about his old characters and more about his status as a "survivor" of cancel culture.
He’s one of the few people who can tell Lorne Michaels "no." Rumors always fly that he changes his monologue at the last second. In 2022, he reportedly did a completely different set for the dress rehearsal than he did for the live broadcast. That unpredictability is exactly why people tune in.
A Legacy of Discomfort
If you're looking for clean, safe comedy, Chappelle on SNL isn't for you. He’s going to smoke a cigarette on stage (even though it's against fire code). He’s going to stutter through a line because he’s riffing. He’s going to make you wonder if the writers are cringing backstage.
But that’s the point.
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Most SNL sketches are forgotten by Sunday morning. Chappelle's sketches—like the "Election Night" bit with Chris Rock where they watch white liberals slowly realize Trump might win—are studied in college courses now. They captured a specific, raw feeling of "I told you so" that most media outlets were too scared to touch.
What to Watch Next
If you want to understand the full arc of Dave’s SNL career, don't just look for the viral clips. Watch the transitions.
- Watch the 2016 "Walking Dead" sketch: It’s the perfect blend of Chappelle's Show energy and SNL production value.
- Analyze the 2022 "Potato Hole" skit: See how he uses silence as a comedic tool.
- Find the "Election Night" sketch (2016): It’s perhaps the most accurate portrayal of American political divide ever aired on late-night TV.
The next time Dave Chappelle hosts, don't expect a peaceful night. Expect to be a little bit annoyed, a little bit shocked, and probably more than a little bit thoughtful. That’s just how he operates. He doesn't want your approval; he wants your attention. And he usually gets it.
To get the most out of these sketches, it helps to watch the full episodes rather than just the highlights. The context of the musical guests—like Black Star in 2022 or the Foo Fighters in 2020—often reflects the specific "vibe" Dave is trying to curate for that week.