A lot of material from the seven (!) Netflix specials Dave Chappelle has put out in the past decade feel less like polished bits than highlights from a theoretical Dave Chappelle podcast. However, one venue he appears to take more seriously than Netflix’s stand-up vertical is the SNL stage in the immediate aftermath of a Donald Trump election — a forum he presided over in 2016 and 2020. As he candidly said of this gig while preparing for it last time around, “[T]he beauty is in trying to help people feel better in a time when they so desperately need it.”
Although simpatico stand-up, Bill Burr, pinch-hit this round on the first SNL after November’s election, Chappelle has returned for the last show before Trump reclaims the White House on Monday. While it’s a bit later than usual, he clearly still views this episode as another post-election chance to be the Voice of the People, soothing a polarized nation with comedy when they need it most. For many, it may be harder than ever to buy him in this role.
Chappelle spent a significant chunk of his Netflix run punching down at trans people. It’s something he loves to do. How do I know that? Because during his 2023 special, The Dreamer, he literally said, “I love punching down.” Perhaps he cynically loves it because punching down creates attention-grabbing controversy that his benefactors at Netflix are pot-committed to riding out. (The closing credits of The Dreamer featured a photo of Chappelle and Netflix’s Ted Sarandos smiling together.) Maybe he loves it because he’s legitimately uncomfortable with trans people and resents being asked to rein in that discomfort. The results are the same, though, either way. Chappelle made a special project of stoking anti-trans hostility during years in which that sentiment galvanized throughout America, to the point where the newly elected president vowed in December to “stop the transgender lunacy” in his upcoming term.
It is within this context that Chappelle screwed on his Earnest Mode face during this week’s SNL monologue and beseeched Trump to “have empathy” and not forget his “humanity.” (Legendary empathy-haver Dave Chappelle, ladies and gentlemen.) I don’t doubt his sincerity in speaking up for displaced Palestinians and victims of the Los Angeles wildfires, as he did during this segment of his marathon monologue. However, for a cultural icon of Chappelle’s caliber, with his demonstrated capacity to advocate for marginalized groups, for someone like that to consistently reduce the trans community to icky, screechy scolds right as their very existence is being legislated away is a waste and a disgrace.
Looking past this glaring, harmful hypocrisy was easier when Chappelle last hosted SNL in 2022. Partly, it was because there was no general election that year, and thus no need for Chappelle to adopt his Voice of the People persona during the monologue and make that empathy gap explicit. It also helped that the surrounding episode was exceptional.
More than his previous turns as host, that one seemed the most like a successful experiment to graft the sensibility of vintage Chappelle’s Show onto modern-era Saturday Night Live. This episode, the first of 2025, instead mostly just comes across as bog-standard SNL — typified by one sketch Chappelle couldn’t even be bothered to appear in.
Here are the highlights:
MSNBC Special Coverage Cold Open
As much as Chappelle is meant to be the unifying force in a divided time, this week’s cold open does a pretty strong job on that front too. It’s got something for everybody. MSNBC’s primetime lineup gets roasted for being “basically like the Avengers for your aunt,” while Donald Trump is portrayed by James Austin Johnson, as ever, like a chaotic, narcissistic clown of doom. (His plan to defeat the California wildfires involves “filling the Up house with water balloons.”) The true target here, though, is the symbiotic relationship between Trump and all liberal-leaning media — each side opposing the other while obsessed with the content they can wring out of it.
Dave Chappelle Standup Monologue
At 16 minutes and 49 seconds, Chappelle’s monologue this week is the longest in SNL history. (As The Latenighter points out, the No. 2 and No. 3 slots are occupied by previous Chappelle outings.) Despite his more contemptible tendencies of the past decade, Chappelle is a tremendously gifted stand-up at heart, and these sprawling monologues are always exciting. Seated and blasting a cig, he takes rascally delight in exploring taboo opinions. He tells a story that suggests maybe there was some pet-eating going on in Springfield, Ohio, and comes dangerously close to defending Sean Combs. Needless to say, not all of it lands. The joke about West Hollywood being spared from the wildfires because its residents are already “flaming,” for instance, is more groan-worthy than offensive. One need not agree with any of it, though, to laugh at some of it or just be riveted by the edge-of-your-seat experience of watching what Chappelle will dare to say on live TV.
Evacuation Alert
During the monologue, Chappelle winks at the camera after suggesting it would be in poor taste to make jokes about the wildfires. Of course, he’s going to make jokes about the wildfires. The rest of the episode’s efforts at finding humor within the grim, still-unfolding catastrophe lands in this sketch. Chappelle plays a patriarch whose secret life spills out into daylight while he and his family prepare to flee the fires. What makes this premise work is the level of gruesome absurdity it eventually reaches, each beat escalating a little further.
Weekend Update: Michael Longfellow Pleads For TikTok to Not Be Banned
Although they started out more like stand-up, Michael Longfellow’s Weekend Update appearances have often leaned more on gimmicks recently, like dressing up as Dilbert or a groundhog or a cigarette. This week, he gets back to basics with a no-frills plea to save TikTok, culminating in his getting bored with the moment and trying to “swipe” Michael Che away. It’s not just a highlight of the episode but one of Longfellow’s finest moments altogether.
Weekend Update: The Original Nosferatu
Just the image of Sarah Sherman decked out like Max Schreck is already comic gold. The decision to make the character a roast comic — with a signature mic-drop joke punctuation, repeated a bananas number of times — takes this desk piece to the next level.
Cut For Time
• There was a lot of talk on X, The Everything App, about Chappelle’s impressive bulge during the monologue.
• If the Immigrant Dad Talk Show sketch looked familiar, it’s because it first appeared in the Ramy Youssef episode from last March. If I remember correctly, that episode also marked the last time a host of the show spoke up for Palestinians during the Israel-Hamas war.
• Musical guest GloRilla had an incredibly cool entrance for her first number, her silhouette appearing in a tight close-up from behind prison bars before that chunk of the set floats away and she starts dropping bars.
• “RFK Jr., who has been preparing for his confirmation hearing by setting his tanning bed to Tropic Thunder,” is the Weekend Update banger of the week.
• Never has the SNL resurrection of Chappelle’s Show characters like Silky Johnson and Donnell Rawlings’ Ashy Larry felt more like afterthoughts than during this week’s Pop The Balloon sketch — a parody of a popular YouTube show you can be forgiven for never having heard of before.