Critic's Notebook: Dave Chappelle Helps 'SNL' Process Another Election, With Mixed Results

Dave Chappelle hosts the Nov. 7, 2020 episode of 'SNL'
Will Heath/NBC

If you're looking for serendipity, November 7, 2020, marked the fifth anniversary of that time Saturday Night Live boss Lorne Michaels decided to toss equal time regulations into the dumpster and semi-legitimize the presidential campaign of former NBC colleague Donald Trump in the name of ratings.

While waiting for Joe Biden to address the nation for the first time as president-elect on Saturday, I dedicated a bit of my afternoon to watching some clips from that Trump-hosted episode. Despite a career of more comic highs than most people can dream of, Michaels should remain ashamed of it — not just because of its political implications, but because of what a wretched piece of comedy it was: an episode on which everybody involved looked like they were either being held hostage or were waiting for the ink to dry on their respective contracts with the Devil. Nobody had a clue what was interesting, funny or significant about a campaign that few believed, several months from the actual primaries, was going to amount to anything. It was bad because it propped Trump up at a moment he was nothing, and it implicitly treated protests against his early candidacy like something to laugh off. And it was bad because it was dismal writing for an inert guest host.

Not surprisingly, nobody mentioned that particular anniversary on this week's Saturday Night Live, which had a different sort of serendipity: Dave Chappelle was back as host four years after he hosted the first episode following Trump's election in 2016.

There was more meat to that earlier hosting stint. Chappelle's monologue was preceded by the Kate McKinnon (as Hillary Clinton) rendition of "Hallelujah," which, depending on your perspective, was either rawly cathartic or the peak of liberal self-obsession — but either way not something to be forgotten. The episode also included the astonishing "Election Night" sketch in which Chris Rock dropped by to help deconstruct white liberal confusion about Trump's win.

It's hard to imagine anybody dwelling much on this week's election cold open, which was bizarrely limp and disconnected from anything that folks have been discussing or feeling about the state of American democracy over the past five days. It was path-of-least-resistance, autopilot writing, starting with Beck Bennett and Alex Moffat's non-impressions of Wolf Blitzer and John King of CNN. Using those two for a framing device already proved how badly out-of-touch the show was; MSNBC's Steve Kornacki was without question the buzziest media figure of Election 2020.

Since nobody could be expected to hold off on writing the cold open until show night, Jim Carrey's Joe Biden appeared for a victory speech that bore no resemblance (other than Maya Rudolph's white suit) to the real speech Biden had given hours earlier. And I guess that was fair, because Carrey's Biden still has no resemblance to the actual Joe Biden whose popular vote total has now gone over 75 million. At this point, I'm exhausted by Carrey's lack of interest in impersonating any aspect of Biden's voice, physicality or personality circa 2020. It's my sincere wish that they'd find somebody else to tackle the role going forward, or maybe just find a way not to have to do a White House sketch every week.

The episode feigned as if the show was saying goodbye to Alec Baldwin's Donald Trump, just like Twitter spent much of today pretending that the actual Donald Trump is just a puddle of water at a Kansas girl's feet, rather than the very real president of the United States for at least a minimum of two-plus more months. Echoing McKinnon's Leonard Cohen/Jeff Buckley cover, Baldwin's Trump sat at the piano for a mournful cover of "Macho Man," which was… definitely a thing that doesn't need to be discussed.

For his part, Chappelle took the stage with admitted nervousness and then delivered what has become a patented blend of unique, uncomfortably personal truth-telling and canned audacity-for-the-sake-of-audacity just because he likes watching people squirm. The question with Chappelle has become what the balance of those elements is going to be. Sometimes he even covers that spectrum in the same elaborately unfolding joke. Look at how he progressed from mocking white people refusing to wear masks to jabbing the knife in and twisting hard: "Don't wanna wear your mask because it's oppressive? Try wearing the mask that I've been wearing all these years. I can't even tell something true unless it has a punchline behind it." I'm not sure when I've last heard a crowd transition from "Ha ha" to "Oh shit" so abruptly.

Transitioning to Trump, whom he urged the 30 Rock audience to at least give a chance to back in 2016, he changed his tone a bit. "I thought the guy was at least an optimist," he said, cracking that his own approach is to look at it like "There's bad people on both sides." The audience wasn't sure how to respond to that.

Chappelle had Trump/coronavirus jokes. "Called the coronavirus the Kungflu. I said 'You racist, hilarious son-of-a-bitch. I'm supposed to say that, not you. It's wrong when you say it.'"

That was followed by a joke that somehow tied a female virologist not telling Trump not to drink bleach to the wage gap — a joke that probably needed two or three more steps to become funny, which didn't stop Chappelle from suggesting that the audience wasn't laughing because they were triggered. He came closer to triggering than that with the crack, "Trump getting the coronavirus was like Freddy Mercury getting AIDS. Nobody was like 'Well how did he get it?'"

Freddy Mercury AIDS jokes? Edgy, man. And this after briefly mocking Ronald Reagan for his approach to welfare? Come on. Connect more dots and connect them better.

As he did last time, Chappelle tried to strike a reconciliatory tone, tying white economic insecurity — specifically among disgruntled Trump supporters — to declines in life expectancy to the opioid epidemic to the plight of even police officers who feel impotent and endangered. He compared all that to the insecurity he (and many other people) have long felt. "Here's the difference between me and you: You guys hate each other for that and I don't hate anybody. I just hate that feeling. That's what I fight through. That's what I suggest you fight through," Chappelle said. "You've gotta find a way to live your life. You've gotta find a way to forgive each other. You've gotta find a way to find a way to find joy in your existence in spite of that feeling."

As for the rest of the show? Well, it's Saturday Night Live, so of course it was a mixed bag! The first sketch, featuring Aunt Jemima and Uncle Ben being fired from their jobs, with Chappelle as Dennis Haysbert and Pete Davidson as Count Chocula was hilarious. Weekend Update was, as it has been all season, a real highlight especially with Michael Che's new boozing, clip-on-tie-wearing disregard for boundaries. Che has been spectacular this season and his dynamic with Colin Jost has never been better.

But at a certain point, the episode ran out of energy, not at all surprisingly since the show has done six straight live shows and Saturday Night Live never does six straight live shows. Weekend Update was followed by two straight local news parodies, making three consecutive sketches with people just sitting at desks. That's bad, and the third of those sketches, with two Black anchors reflecting on a White Bronco chase featuring Don Junior at the wheel didn't have a set-up or a punchline. There wasn't even a sketch after the second Foo Fighters performance. How much of that related to giving Chappelle 15 minutes for his monologue and how much related to writing fatigue? Your guess is as good as mine.

Saturday Night Live won't be back until December and they, like all of us, could use some rejuvenation. Who knows how much crazy election stuff could happen between now and then? Maybe they'll even figure out a solution to their Biden problem.

Whatever comes next, though? No Trump cameos, Lorne. It was only five years ago. We remember.