In a moment that blends comedy, cultural commentary, and historical hindsight, Dave Chappelle recently peeled back the curtain on what the Saturday Night Live writers’ room looked like the week Donald Trump stunned the world by defeating Hillary Clinton in 2016. Spoiler alert: it wasn’t pretty — unless you’re into irony.
Appearing on Variety’s Actors on Actors alongside fellow comedian Mo Amer, Chappelle didn’t hold back as he described the atmosphere at 30 Rock in the days leading up to his now-legendary post-election SNL episode.
“When they called Donald Trump the winner — that s*** shut the writers’ room down,” he recalled, to roaring laughter from Amer. “They was crying… They couldn’t believe this was happening.”
Dave Chappelle reveals what the SNL writer’s room looked like when Trump got elected in 2016: “That s**t shut the writers room down.”https://t.co/VW4gwr7t8l pic.twitter.com/JwHTe9nyd9
— Variety (@Variety) June 4, 2025
The irony, of course, is that SNL — a show built on satire, shock, and poking fun at the elite — was filled with people devastated not by a national tragedy, but by the election of a man their industry simply couldn’t process. In that moment, the show itself became an unwitting parody. It was comedy gold — if only they’d had the self-awareness to see it.
Chappelle’s hosting gig that week became instantly iconic, not just for the timing but for his measured monologue. In a media landscape defined by hysteria, he went against the grain, famously saying: “I’m wishing Donald Trump luck. And I’m gonna give him a chance. And we, the historically disenfranchised, demand that he give us one too.”
In hindsight, Chappelle acknowledges some of those words didn’t age the way he might have hoped — but he doesn’t flinch. “That’s what it felt like in that moment,” he explained, comparing the monologue to a photo in time. And he’s right. It captured a national mood, or at least a slice of it that Hollywood had trouble recognizing existed: skepticism, curiosity, and a sliver of hope for unity.
Contrast that with where SNL went in the years that followed — deeper into caricature, often discarding nuance in favor of predictable political punches. The show that once skewered the powerful became a safe space for elite consensus.
Just this year, SNL offered up a skit where Tom Hanks — Hollywood’s everyman — played a Trump voter too afraid to shake a Black man’s hand. A cartoonish and tired portrayal masquerading as edgy comedy.
Chappelle’s revelation reminds us that while the 2016 election may have stunned the media and entertainment elite, it didn’t surprise everyone. Some saw it coming — not because they approved of everything Trump stood for, but because they had their ears to the ground outside the coastal echo chambers.
