Dave Chappelle answers Saturday Night Live's call to flattery

It’s rare for a genuinely towering figure in sketch comedy unrelated to Saturday Night Live to actually host Saturday Night Live, because there isn’t a whole hell of a lot of high-profile sketch comedy on the airwaves these days outside of the extremely mainstream institution of SNL itself. I imagine that’s why it’s hard for SNL – or at least certain folks behind the scenes – to let go of the idea of Dave Chappelle as a frequent host, even when Chappelle himself has seemed, at times, fairly disengaged by the idea of actually showing up, either at all or in sketches. He’s in the extremely rarified position of having done some of the most beloved sketch comedy of all time and walked away from it early enough to create some real British comedy-style scarcity—so just imagine, coaxing Chappelle onto your show and getting a few more sketches out of him! The only catch is that you have to let him do a very long, uneven stand-up set. Oh, and he might not do the sketches.

Obviously, I’m being a little facetious. Chappelle is also known for his stand-up, and he can still sidewind his way towards a surprising or cathartic punchline in between drags on his cigarette. (Cigarettes?! On live television? Now we’re getting dangerous!) In this episode’s 16-minute monologue, he mentioned that he’s trying to stay out of trouble, alluding to the controversy he’s courted, sometimes seemingly out of spite, in making anti-trans jokes on his series of Netflix specials, which I’m sure some poor soul in the comments will inform me is actually cutting-edge stuff. (This excellent, searching yet absolutely clear-eyed piece on his last one convinced me it might be a frustrating experience, so most of my experience with his most recent stand-up comes from these SNL mini-sets and YouTube clips.) He then proceeded to try out some knowingly premature material about the Los Angeles fires; went into a half-developed idea about the fires providing evidence of his hatred of the poor; dipped into some conspiracy-minded thinking (arsonists being responsible for the Los Angeles disaster; treating Diddy’s legal trouble as some kind of cancellation) before quickly backtracking (including a very funny, funnier for his casual delivery, of how Diddy somehow got a RICO case going over just one guy); riffed on Diddy some more, including some of his best and silliest jokes; riffed on Trump a little bit; offered a sincere tribute to Jimmy Carter and a free Palestine, along with a sincere entreaty to Trump much like the one he closed with eight years ago and change; and, you know, generally favored us with that greatest of all wisdom, that of the wealthy stand-up comic. Oh, and he also got to do his version of Kristen Wiig’s “don’t make me sing!” character, explaining that Lorne Michaels once again asked him to host the post-election episode, and backed himself into committing to a January episode closer to January 6 and the impending Trump inauguration. Dave, please! Please reluctantly accept the hosting gig and proceed to sit out a bunch of the show! We need you now more than ever!

Look, Chappelle still has something. Even the fact that he treats SNL with a kind of smug indifference can be thrilling. You can be pretty sure, going into a Chappelle episode, that you’re going to get a monologue that will take up not just more of that slot than usual (as most stand-ups do), but a substantial portion of the episode overall. That on its own has a nicely destabilizing influence on the show’s sometimes-tedious patterns, and on top of that, you have no idea how many sketches he’s going to do. The first time he hosted, back in 2016, he was there all night, bringing back Chappelle’s Show bits and mocking white shock over Trump’s first victory with glee. Other episodes, he’s dipped in and out, especially the 2020 installment. (Honestly, stick a monologue on that episode where he inexplicably turned up for the goodnights, and you could claim he hosted that one, too.)

It’s a little difficult for me not to picture how it actually might be to work with Chappelle during the week leading up to these episodes, especially when he directly brings it up while smoking through his monologue and sometimes, as was the case tonight, at least one sketch. But in the sense that he brings some unpredictability back to the show, he does what Michaels is apparently on the phone begging him to do. Hell, even the quality of his monologue will be unpredictable! Doubtless he considers his potential for genuinely off-putting (or just not all that well-formed) jokes as part of the whole act, though recent years have made it seem like he does so a lot more self-seriously than necessary. It doesn't help that Michaels, by orienting his appearances around various political divisions, positions him less as a sketch-comedy legend than a soothsayer for our trouble times or whatever. But the idea of Chappelle's episodes very much feels like a throwback to the first five seasons, which is always welcome, especially in an anniversary year.

So please don’t take it as churlishness about Chappelle in general when I say that these episodes might just be a little more fun if he put some effort back into the sketches? If he felt like there was a way for him to communicate through comedy that isn't entirely and exclusively his way or the highway? Considering there were three live sketches and one pre-tape featuring Chappelle’s Show characters tonight, it might have been fun to see Chappelle really throw himself into all three of them, instead of, uh, one.

What was on

Here was the one: a vaguely sloppy but undeniably entertaining sketch where Chappelle played a man making a few final arrangements before he and his family evacuate during the Los Angeles fires. This sketch had everything: multiple secret storage compartments, heavy blood splatter, an ass-stored treasure map like in Three Kings, dog murder, and Chloe Fineman speaking French. Did the set-up totally come through before the sketch set off and running? I'm not sure. Did Chappelle seem deeply committed to the entire thing, including the dog murder? Absolutely. "Eat the heart" was a great shock laugh.

What was off

There was nothing really wrong with the "Immigrant Dad Talk Show" coming back; it's a format built to recur, but on the other hand, there's something pretty insulting about just doing the sketch again with the same character as the guest. (You know, the touchy-feely dad played by, well, the guy who plays anyone who affectionately calls a kid "buddy.") It really felt like the show was saying to Chappelle, no worries, we'll just start it over with you! Whatever you want!

Most valuable player (who may or may not be ready for prime-time)

Is it weird to say Kenan? For a sketch Chappelle didn't deign to appear in, even though he could have played any of the four parts? The sketch with Devon Walker describing his missing girlfriend to the police, urged in a less honest direction by Kenan's lurking janitor, had a predictably sour punchline, but it's nice to get one of those periodic reminders that Kenan's perfect timing and peerless mugging abilities are a fascinating experiment in having someone do sketch comedy regularly for two full decades, something that, like sketch comedy as beloved as Chappelle's, simply can't occur that often. This is all to say that when his janitor character fake-answered the phone in the background, I laughed out loud.

Next time

Bowen Yang's extremely online reference to Club Chalamet must have been prep for Timothée Chalamet's third hosting gig next weekend, and first time as (official) musical guest. Expect Bob Dylan covers, rather than "Tiny Horse," but you can bet I'll spend the week thinking about Dylan songs way out of the Complete Unknown zone that I'd love to see him try. C'mon, "Pay In Blood"!

Stray observations

• • GloRilla! Punchy, especially that first song! Just what the show needed, given its out-of-wack timing that had Update starting around when it would usually be wrapping up. Good stuff.
• • Trying not to dwell too much on Chappelle offering some behind-the-scenes info, but of course Lorne did actually ask him to host that post-election show that a lot of fans were relieved to see him not host. Maybe the next edition of the Live From New York book will have some insight on what the Chappelle week is like, in terms of pitching sketches to him. Is he prickly, or charmingly low-key, or something else entirely? Why does he ultimately say yes to a show where he seems to find the idea of doing 20 minutes' worth of sketch comedy kinda corny? Or is he just nostalgic for those pre-2000 episodes where sometimes the host would sit out for a sketch or two without recappers fussing over it?
• • Apparently that balloon-popping YouTube show is real. A dating show where you can hear super-concise rejections has great potential for comic rhythm, though the sketch didn't quite harness it.
• • Once Chappelle pushed through the intimation that maybe Diddy was being targeted somehow, it became a perfect subject for his famous-outsider vantage, and the baby oil bit was particularly hilarious.
• • It's not in my nature to criticize Sarah Sherman, not least because she is clearly a practitioner of the horror lifestyle. However: It seems like there's probably a funnier idea involving her in full Count Orlock makeup than just ribbing Jost some more.