Saturday Night Live Recap: Dave Chappelle Takes SNL to a Season High

Saturday Night Live

Dave Chappelle
Season 48 Episode 6
Editor’s Rating 5 stars

Saturday Night Live

Dave Chappelle
Season 48 Episode 6
Editor’s Rating 5 stars
Photo: NBC/Rosalind O’Connor/NBC

When he first hosted Saturday Night Live in 2016, Dave Chappelle famously said he would give Donald Trump a chance.

That was sort of how I felt about Chappelle when I learned he’d be hosting SNL this weekend.

It was a fairly new feeling. For many years, instead of “a chance,” I would simply give Dave Chappelle my wallet and my heart. In fact, I remember where I was — walking to a work thing in Williamsburg — when I saw a tweet about Chappelle hosting the first SNL after the 2016 election. It was an instant hit of pure joy, directly into the bloodstream. That election had engulfed all of America, for far too long, in an ominous aura of pervasive dread, like an imminent car crash in slowest possible motion. Everyone wanted it to just be over but it felt like it would never end and it was difficult to imagine life afterward. The announcement of Dave Chappelle’s belated SNL debut, though — alongside A Tribe Called Quest, at that — was a reminder that not only was this grotesque election finally almost over but that good things awaited on the other side, independent of the outcome. And when the day arrived, Chappelle’s Emmy-winning turn ended up being a bright spot in what was, for many people, a very dark time.

Suffice to say, a lot has changed since then — both in America and in Dave Chappelle. That impossibly long election gave way to three chaotic Trump years, culminating in a somehow-even-more-chaotic pandemic election year, followed by even more chaos. Meanwhile, the rare thrill of seeing Chappelle perform stand-up on TV again during his 2016 SNL monologue slowly curdled into routine with his shockingly prolific run of Netflix specials. Comedy is obviously subjective and a lot of people loved each and every one of these, but to your recapper, they started to feel as tossed-off as they were increasingly bitter and combative. Having one’s jokes appear effortless is a stand-up magic trick, and Chappelle is a wizard at it. However, most of these specials were larded with lots of material that just felt low effort. And all of this is before we even get to the elephant in the studio during this SNL episode.

As you may be aware, Chappelle has faced heavy criticism in the past few years over his material about trans people. He’s been boycotted by Netflix employees, excoriated on Twitter, had a live performance canceled, and got tackled at the Hollywood Bowl last May by a guy whose stated motive for the attack so neatly aligns with a caricature of triggered comedy fans as to seem like a psyop. However, in that same span, Chappelle has also sold out venues everywhere, won an Emmy, made a deal to continue his wildly lucrative business relationship with Netflix, post-boycott, and, uh, been welcomed back to host Saturday Night Live. While some fans might call this ongoing success a victory over those who tried to cancel him, others might call it further proof that free speech isn’t quite as endangered as Chappelle constantly makes it out to be since turning his inherent right to make trans jokes into a hill to thrive on.

“The more you say I can’t say something, the more urgent it is for me to say it,” Chappelle said in What’s in a Name, a 40-minute TED Talk–esque quasi-special Netflix released in July. “And it has nothing to do with what you’re saying I can’t say. It has everything to do with my right, my freedom of artistic expression. That is valuable to me.”

It’s a valid point. At the same time, Job One for a comic is being funny, and while there have been many Free-Speech Martyrs in comedy before — and many currently cranking out cranky content about the fear of cancellation — there have seldom been humans as funny as Dave Chappelle. He’s always been somewhat bitter, but Chappelle used to take rascally delight in exploding the racial inequality that seemed to be the source of his bitterness. Recently, though, he doesn’t seem to be having much fun either in his stunt-y trolling of trans people, or his misguided scolding of those who would dare be offended by the wrong thing. Whether you agree that he’s gotten less funny since leaning practically full-time into grievance and controversy-stoking, it’s almost an objective truth that there is little in the world less funny than closing out a comedy special in 2021 by complaining in earnest that Kevin Hart was unfairly thwarted from achieving his dream of hosting the Oscars.

All of this is to say that by late 2022, I’d become indifferent to Dave Chappelle. The idea of wading through another hour of cancellation-themed humor to see if he’d actually be funny while exercising his right to poke the bear seemed like a snoozy chore. When SNL announced a threepeat of his post-election hosting tradition, though, I was willing to give him a chance. I wasn’t expecting him to help deliver by far the most consistently funny episode of the season.

Here are the highlights.

Stand-up Monologue

Clocking in just shy of his 16-minute monologue during the 2020 episode, Chappelle got the crowd roaring right away and seldom let up. Clearly, he went through some “there but for the grace of God go I” in the past month while watching Kanye torpedo both his reputation and his fortune — and thankfully he shared that experience with the rest of us. It was electrifying to watch him get close to the third rail of antisemitism while putting Kanye on blast for outright grabbing it, and explore the space in between. While he covered a lot of other ground in the monologue, his material about Kanye and Jews felt like a smarter and funnier expression of his comedic mission to test boundaries than anything that’s landed him “in trouble” on Netflix.

However, while he appeared to be coming at this material as an experiment in what he could get away with, rather than wanting to normalize antisemitic tropes, the results are largely the same either way. It’s not much of a surprise that the Anti-Defamation League has condemned Chappelle’s monologue. After wisely deciding not to pour gasoline on his previous controversy this outing, it looks like he may have ignited a fresh one.

Potato Hole

The buildup around what a Potato Hole might be goes on for so long, in such intentionally corny fashion, it feels like whatever weird sexual thing it turns out to be will inevitably be a letdown. So, when Chappelle’s bluesman Willie T. Hawkins finally reveals its very real slavery-derived definition, it lands hard. Andrew Dismukes’s anchor slowly putting down Hawkins’s album that he’d been holding up is a perfect punctuation to the main joke in this perfectly timed sketch.

Sarah Sherman Debuts Sarah News

It sorta feels like all that antagonizing of Colin Jost on “Weekend Update” has been leading up to this demented moment. Sarah Sherman fully hijacks the “Update” desk for four howlingly funny minutes of Topical Humor (Sarah’s Version), and I wish she would never give it back.

Heaven Scene

As a premise for a Chappelle sketch, “Black heaven” has a lot of potential. It is far funnier, though, to burn that premise for a fourth-wall-busting bit about Chappelle forcing Mikey Day to star in a sketch about Black heaven for his own devilish amusement. How much fun does the host look like he’s having here, surrounded by Chappelle Show alum Donnell Rawlings and Black Star, enjoying Day’s feigned awkwardness? You really do love to see it.

Please Don’t Destroy — Election Night

I compared Molly Kearney to Melissa McCarthy in a previous recap, but as they appear in more scenes, I’m seeing more shades of Chris Farley. Kearney’s manic desperation here, in trying to avoid becoming the attorney general of Ohio, has the same endearing vulnerability Farley brought to similar silliness. Also, it makes a subtle statement that the final sketch of a show hosted by someone so critical of gender expression ends with Kearney’s pronouns onscreen.

Stray Thoughts

• As a survivor of the year 1999, I appreciated the “Steal My Sunshine” reference in Trump’s rant during the Fox & Friends cold open. (James Austin Johnston’s uncanny mimicry of Trump’s stream-of-consciousness rant style is what got his foot in the door at SNL.) Also, Ainsley Earhardt (Heidi Gardner) wondering whether she was allowed to say “Wakanda Forever” turned out to be a nice tone-setter for the episode, with spiritual echoes in at least three other sketches.

• It’s amazing how long they let this sketch go on as a House of the Dragon parody before revealing that it’s actually a sequel to the Chappelle Show character bonanza from 2016, which centered on Walking Dead. Also, Tyrone Bigguns using dragon fire to light his crack pipe was an inspired touch.

• I have a feeling that Kenan Thompson’s hair clippers buzzing immediately after a white person says something out of pocket is about to become a meme on TikTok, thanks to this barber-shop sketch.

• Sharp jokes all around on “Weekend Update,” but the visual gag of Tucker Carlson, “seen here trying to make it through No-Nut November,” was the killer line.

• With his debut of unlikely presidential hopeful Jose Suarez, new cast member Marcello Hernández is now two-for-two on “Weekend Update” desk pieces this season.

This recap has been updated.

Saturday Night Live Recap: Dave Chappelle Delivers