Dave Chappelle hosts for 4th time with musical guest GloRilla

Welcome to 2025, Conehead nation! There’s so much Saturday Night Live content these days, I can barely keep up. Documentaries, 8H “experiences” and now, oh yes, the return of season 50.

Dave Chappelle hosts the first episode of the new year, in his fourth gig. The previous episodes hosted by the legendary (if increasingly controversial) stand-up were mostly grounded in election reactions; they were November shows. Tonight’s episode also has a political twinge — we are less than 48 hours from the end of Joe Biden’s presidency and the return of Donald Trump to the White House. How will Dave make sense of this?

I am honored to be joined tonight with commentary with former SNL cast member Jerry Minor, who is planning to launch a new podcast with ECamm, Playing to the Back of the Room. On Chappelle, Minor shares: “I’ve always been a big fan… I think he’s great, and he’s usually a really good host.”

Reflecting on the pending Trump 2.0 era in comedy, Minor thinks it will be hard to strike the right tone in terms of political jokes: “Obviously shows like Saturday Night Live will continue to do them. But how does that happen? How do people make fun of him? How mad is he going to get at the way people make fun of him?” He adds: “During the 2000 election, Bush and Gore both came to SNL and did bits. Back then both candidates would probably make an effort to at least make some kind of appearance on the show… Even then we felt like no matter how I felt about either candidate, there was always an effort not to get too close to them, because I knew I was going to have to make fun of them.”

Scroll down and be merry folks. Hopefully our friends at 8H are well-rested and ready to meet the moment.

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Cold Open

It’s a special MSNBC Report with Rachel Maddow (Sarah Sherman), who is back on TV for inauguration weekend. Chris Hayes (Andrew Dismukes) is “Woke Sheldon” as part of a group of progressive Avengers for our collective aunts — the group promises to not chase every crazy Trump statement. But sure enough, they cannot resist — every statement from Trump distracts them. Real policy is too boring. 

Meanwhile, Joy Reid (Ego Nwodim) is calling out Chloe Fineman’s Stephanie Ruhle for trying to hook up. And Marcello Hernandez keeps quoting old pop songs, including “The Real Slim Shady.” As Trump himself puts it, the anchors are awful, like Scooby Doo “All Velma”. They cut to James Austin Johnson’s Trump, who introduces the latest member of his cabinet, the pathological liar George Santos (Bowen Yang). Interesting the show thinks of Yang’s Santos as a fan favorite. 

This is an OK media critique as the show starts thinking through its stance on Trump and the new normal. Not brilliant or ambitious in its satire, but solid. 

Monologue

Chappelle comes out wearing a great-looking suit and smoking a cigarette. He says he’s in a pickle — Lorne Michaels asked him to do the election episode back in November but he declined. He kept pushing it off until deciding it was time to get rid of his old Trump jokes. Now, the L.A. fires have changed things. Is it too soon to joke about celebrities’ homes being destroyed? While he’s tired of being controversial, he gives it a shot. He talks about poor people, West Hollywood, Luigi Mangione, and conspiracy theories. 

He turns back to Trump and the rumors that Haitian immigrants were stealing and eating pets in Springfield, Ohio. He tosses his cigarette to the ground, lamenting it’s no longer fun being famous. With some understatement, he notes Diddy is in a bit of trouble! Is he ugly, Dave wonders? Or, does he just have snitch energy? The baby oil bit here is a highlight for me. This must be one of the longest monologues of the season. He returns to Trump and the death of Jimmy Carter, and tells a moving story about the former president going to Palestine. He salutes Carter’s courage and leaves a message for Trump — and all of us. “Do better,” he implores. Show decency to people whether they live in the Palisades or Palestine. Moving and classy.

While Minor shared he is not a huge fan of a lot of modern stand-up, Chappelle remains someone he wouldn’t mind working with as far as sketch. Minor has crossed paths with Chappelle in the past noting: “Comedy Central had an award show years and years back, they only did that for three or four years. I was a performer. I think he got an award that year, maybe best stand up.”