At 16-1/2 minutes, Chappelle's monologue was one of the longest in Saturday Night Live history. It also -- after a long overtime college football delay -- resulted in fewer sketches. "Last night’s Saturday Night Live was an odd beast," says Dennis Perkins. "On the one hand, having Dave Chappelle host the first post-election episode when Donald Trump is on the ballot hasn’t previously been exactly a good-luck charm. On another, the show itself—complete reversal of fortune for the nation aside—was marked by one thudding low (Alec Baldwin’s final-ish Donald Trump, with Jim Carrey channeling Ace Ventura, for the cheap seats), and then a rushed and incomplete-feeling two-thirds. ('Weekend Update' was uncharacteristically short, there weren’t many sketches, with a last sketch seemingly and awkwardly cut for time.) But the reason for the rest of the show feeling thin was, by any account, worth it, as Chappelle took the stage for an epic, most likely record-breaking 16-and-a-half-minute monologue. When you’ve got Dave Chappelle, you give Dave Chappelle all the time he wants—even if, as he related in a mid-set anecdote, some of his Ohio neighbors aren’t thrilled with his COVID-controlled, celebrity-luring cornfield stand-up shows. Chappelle showed up in a few sketches, but it was the monologue that everyone’s talking about, a thoughtful, pointed, and effortlessly light-footed set that had the in-studio audience alternately applauding, yelping hysterically, listening intently, or, in a few cases, sucking in air in shock through their mandatory pandemic masks."
Comparing Dave Chappelle's 2016 and 2020 post-presidential election monologues: "After two elections involving Donald Trump, SNL has invited Chappelle to host, treating him like a moderator for our greater national reckoning, a comedian seasoned and blunt enough to broach sensitive matters of importance. Both times, he’s opened his set by pointing out that much ails America beyond the contentious election it just endured. His monologue on last night’s episode took plenty of jabs at Trump and his administration’s handling of the coronavirus pandemic. But the thrust of Chappelle’s comedy was wider and darker. He urged the audience to consider the grievances of millions of voters feeling abandoned or adrift in their own country, connecting those feelings to the lived experiences of generations of Black Americans. Chappelle barely mentioned president-elect Joe Biden at all. Instead, he built to an argument that no president can save America if Americans don’t want to save each other. Watching both of Chappelle’s SNL monologues, his consistency is all the more striking because the two episodes around them are so different. In 2016, after Trump’s victory, a mournful pall hung over the show. Kate McKinnon tearfully sang 'Hallelujah' in costume as Hillary Clinton, a bizarre spectacle that reflected the shell shock of the show’s writers and actors following Clinton’s loss. In 2020, the show winked at the strange self-seriousness of that earlier moment by having Alec Baldwin as Trump sit down at a piano to perform a somber version of the Village People’s 'Macho Man.' The rest of the episode was filled with typically upbeat, ridiculous material; on 'Weekend Update,' co-anchor Michael Che sipped a celebratory drink while reading his jokes."
Jim Carrey's Joe Biden impression finally pays off with a nod to Ace Ventura: "Jim Carrey’s otherwise inexplicable Joe Biden impression makes a certain amount of sense as a long lead-up to the Ace Ventura 'Loser' bit this week, and although the game wasn’t necessarily worth the candle, it was still pretty satisfying when he finally said the line," says Matthew Dessem. "As for Alec Baldwin, a sad piano rendition of 'Macho Man' was the perfect exit for his Trump impression, and a reminder of how much better most Americans feel today than when Kate McKinnon sang 'Hallelujah.'"
Chappelle’s monologue veered away from the biting tone you might expect from the incisive, no-holds-barred comic: "Wearing a great suit and apparently smoking a cigarette onstage — in his defense, this was the kind of week where a performer of Chappelle’s stature could probably get away with smoking on an NBC soundstage in front of a studio audience — Chappelle’s set kept with his ongoing themes of calling out racist double standards in the US," says Aja Romano. "Chappelle started out the monologue by talking about his great-grandfather, a slave he has spoken about before, most notably in his sober commentary on the killing of George Floyd earlier in 2020. But rather than using his great-grandfather’s story to begin a commentary on the many racial and social issues facing America today, Chappelle veered into the unexpected, pivoting to a self-deprecating joke about his current Netflix and HBO specials that set the tone for the rest of the set — and arguably for the rest of the show, which seemed determined to skew toward the calm, even apolitical end of the spectrum."
Chappelle's monologue was an illuminating mess: "When Dave does television, he sets out to destroy it," says Craig Jenkins. "The culture war posturing is getting old; in a perfect future, 'Did I trigger you?' is a relic of the year the country nearly broke in half from people going out of their way to spite each other. On the night where we began to dream up our next phase, Dave Chappelle’s celebration of the enduring Black American spirit that helped make it possible — and lessons for white Americans whose grievances became a mandate for the orange man whose election loss sparked a worldwide dance party — made for a satisfying conclusion. It was maybe a bit of a mess, but it was an illuminating mess."
Chappelle's monologue was "hit-and-very-miss": "Chappelle gives a long, 16 minute monologue," says Dustin Rowles. "Some of it works; some of it does not (AIDS jokes in 2020? The crack about women deserving to make less money?). He also sums up the current moment by saying that we need to find a way to find joy in our lives and to also forgive. This space right here is probably not the place to get into this debate about Trump and forgiveness, so I’ll leave it at that. As a monologue, however, it was hit-and-very-miss."