Dave Chappelle SNL Sketches Ranked: Kanye and Kyrie Under Fire, Breaking Up with Trump

The show opened with a dominant standup monologue by Dave that took up more than 15 minutes. Whereas “SNL” usually averages somewhere between 10 and 11 sketches, outside of “Update” and the monologue, there were only six this week.

They did make the most of those six, though, opening the show with a brilliant reaction to the midterm “red wave” that didn’t happen by having “Fox & Friends” publicly break up with Donald Trump. Dave also brought back some of his “Chappelle’s Show” characters, this time to invade Westeros in a “House of the Dragon” parody.

In his monologue, he went in relentlessly on Kanye West’s ongoing controversies, as well as those impacting Kyrie Irving. He also talked about the midterm elections and the power that Trump still holds in middle America that so many on the coasts didn’t understand before he got elected, and still don’t seem to fully grasp.

It was a tight piece, but also one that left the audience uncomfortable at times. Chappelle has courted controversy plenty in recent years, and had many call for his cancellation -- both as host of this show and as a comedian in general. And yes, he touched on this as well.

The funniest sketch of the night, though, was one that Chappelle wasn’t even a part of … though that was kind of the whole point. There was a lot of brilliantly sharp writing and performances on the night, but this meta-sketch will probably go down as an all-time classic.

As usual, we're ranking all the sketches from worst to first, including the Monologue, Cold Open, "Weekend Update" and any sketches that were cut for time but made their way online. We'll skip the musical guests, because they're not usually funny -- unless Ashlee Simpson shows up. We wrap up with a look at the cast-member who had the strongest week.

Dave Chappelle actually set up this clip by talking about how odd it was seeing Black characters with that “blonde” hair and old-timey speak on the “Game of Thrones” spinoff. Like his “Walking Dead” parody a few years back, this pretaped sketch was Dave’s opportunity to trot out some of his favorite “Chappelle’s Show” characters like the pimps from “The Player Haters Ball” -- complete with Ice-T and Donnell Rawlings reprising their characters -- Rick James-ish and, of course, Tyrone Bigguns. Unfortunately, it wasn’t nearly as funny as the “Dead” piece as the characters weren’t as outrageous. We got more laughs out of James Austin Johnson as King Viserys, physically falling apart as we watched, than any of Chappelle’s characters.

Probably the funniest visual was when “Fox & Friends” slowly closed the window where James Austin Johnson’s Trump was standing after breaking up with him following the lack of “red wave” in the midterms. The whole premise of this bit was how the Trump sycophants had gotten an order to “move on.” Luckily, they still had some love for Kari Lake, as she holds onto hope of a victory and prepares to cry foul if she loses. Cecily Strong’s Kari Lake had the cool resolve to change her narrative from rigged election to sound democracy depending on whether or not she’s ahead in the polls, which changed by the moment in this sketch. As always, James’ rambling is a highlight, but we appreciated the more subtle tone of this whole piece, treating it like a real breakup.

A great premise with the white newscasters playfully trying to guess what a “potato hole” is only to be told by their musician guest it’s historical meaning as a place where Black slaves hid their food and possessions from slave owners. Dave Chappelle’s impassioned (in character) explanation was paired with the perfect music as all the white people nailed their deeply uncomfortable reactions after playing with the phrase like it was sexual or sports related. Booker T. Jones had an actual album named after this back in 2009, but we can only hope he never faced such an uncomfortable moment. This was definitely more in the line of cringe comedy than laugh-out-loud humor.

This turned out to be a very fun absurdist sketch about Molly Kearney accidentally throwing their name out for Ohio Attorney General and then winning the election. The boys helped prepare them for their big speech (in five minutes), setting them up with a new look and fake family. It was all so haphazard and chaotic, you couldn’t help but laugh at the absurdity of it, as well as all the ways Molly was diminished as a member of the “SNL” cast (being called a background character and stagehand). This was a pretty good showcase for Molly’s capabilities, even if it was relegated to the 10-to-1 slot, as they continue to fight to get their voice and comedic style out there.

In their political segment, Michael Che got some good audience groans (and you know he eats those up) for his joke about the U.S. having more female governors than ever before, and Covid impacting Apple production in China. Colin Jost got a savage joke in on Matt Gaetz about Congress’ first-ever Generation Z member, but the audience seemed more receptive to bashing him. They also took on Democrats retaining Senate power, Biden considering re-election, and the turn against Trump by Rupert Murdoch.

After more Latinos hit the polls than ever before, Marcello Hernandez came out as character Jose Suarez, a Latino who now wants to be president someday. It was a little over-the-top, but the wordplay he offered did have some fun moments, like talking about the moral of Roe v Wade being that if you have a boat, you can row, but if not, you’re gonna have to wade. His stance was to stop complaining because everything really is okay, and certainly better in America than some other places. Overall, it was an okay piece, but the material could have been tightened up a bit.

It was a short non-political segment but the boys were definitely having fun with real stories about a penis-shaped flight path pointing at Russia and a 10-year-old student getting in trouble for touching his teacher’s breast in Florida. But the best joke again has to go to Che for his punchline about the charges brought against a white college woman who used a racial slur and attacked two Black students. Even the audience was on his side for this one!

No one has more fun on “Update” than Sarah Sherman. This time, she didn’t make up headlines to take down Colin Jost, but rather made her own show (complete with intro and quirky set design) to tell her own “Update”-style jokes about … Sarah Sherman. There was vagina material, crushing hard on John Fetterman and, yes, some more baseless accusations against Colin when he tried to get her to stop.

Dave didn’t hold back right from the jump in a 15 minute standup monologue, opening up with a quick lesson for how Kanye West could “buy yourself some time” with a statement denouncing antisemitism before taking a deep dive into his recent controversies. It was hilariously biting commentary, with us getting a particular chuckle out of him saying “the student had surpassed the teacher” after talking about Adidas being founded by Nazis and still dropping Kanye.

As he got into Kyrie Irving, the audience wasn’t sure how to respond, and he got only one whoop when he said Black people can’t be blamed for Jewish struggles over the years. Clearly this crowd was uncomfortable and uncertain where he was going with all of this. He then tried not to dunk on Herschel Walker “because he’s Black,” but conceded that he’s “observably stupid.”

He saved some time for the ex-president, explaining his strong appeal in the rural communities and frustrations from the left about him at the same time before going in on the war in Ukraine and white people now expressing frustrations about America Black people have been saying for generations.

He wrapped by talking about how scary it is to talk these days, how nervous it makes him to get up and talk to crowds. “I hope they don’t take anything away from me,” he said. Already, his even being selected to host was met with controversy because of things he’s said in the past, so he’s speaking with personal familiarity with the power of cancel culture.

He also made his own jokes about Jewish people in Hollywood, filtered through comedy. While it wasn't perhaps as inflammatory, he was probably skirting the line still by many standards, so it's likely there will be some backlash to these comments, as well.

Typical Black barbershop chatter about everything from Kanye to politics, but the one-note joke of the sketch was the screeching halt the conversation hit every time Michael Longfellow, as a fellow barber, chimed in. They’d talk about Kyrie Irving being questionable since he said he thought the earth was flat, and Michael chimed in about him not wanting to take the vaccine, even after the president said it was okay. It was another brilliantly subtle piece about the differences in white and Black culture on all of these topics and issues. We particularly loved that the reaction to every comment Michael made was a beat of silence and Kenan firing up his clippers. No one ever responded directly to him. This gentle slice-of-life piece was all in the writing, and it was very strong. The sketch even perfectly nailed the landing!

A segment introduced by Dave Chappelle explaining that he’s sitting the next sketch out, but had a replacement lined up to replace him. Had Kyle Mooney still been part of the cast, we can picture him in this role, as the joke was clearly that Mikey Day was filling in for a “Black Heaven” piece, and more than a little uncomfortable with it. He struggled to say lines and stay in character, with the humor coming from just how out of place he was. Mikey was fantastic in this role, as was Kenan trying to support him. Poor Devon Walker continues to struggle to perform in sketches, giving more stilted line deliveries. Dave laughing on the sidelines with Donnell Rawlings and Black Star only added to the awkward brilliance.

This was an interesting night as Chappelle’s monologue ate up a lot of sketch time. There were basically only six sketches, outside of “Update,” which is way lower than the average. That said, there were some notable moments in them.

The biggest takeaway is that we’re not seeing Devon Walker settle in as a sketch performer just yet. His delivery is about as awkward as early Pete Davidson, but he doesn’t have knockout “Update” material as himself to balance it out yet, so he’s really going to need to find his voice.

On the flip side, the biggest performers this week were mostly guys, with Sarah Sherman and Cecily Strong each delivering one extremely strong performance, but either not appearing at all anywhere else, or in a very, very supporting role.

James Austin Johnson kept us laughing as Trump and in a disgusting turn as Viserys, while Michael Longfellow is really stepping up and becoming a solid performer in his own right, holding his own as a white barber in a Black barbershop, even if it was mostly a straight man role. He’s definitely coming out of the gate strongest in this format.

From newcomer to 20-year veteran, Kenan Thompson had a strong night as well, pairing well with Michael in the Barber sketch and cracking us up in the otherwise so-so “House of the Dragon” piece. But his strongest piece was next to this week’s top performer, Mikey Day.

We could almost give it to Mikey for that “Black Heaven” performance alone, as he was flawless in a complex piece that demanded he be in character and out as part of the overall comedy. It was played to perfection, while he also brought his usual consistency to “Fox & Friends” and “Dragon.”

“Saturday Night Live” returns December 3 with host Keke Palmer and musical guest SZA.