The Tragicomedy of Andy Samberg Won Late Night This Week

It’s been a very meta week for late night. First of all, Trump went in on both Jimmy Kimmel and Stephen Colbert this week, prompting both men to respond. And both brought their beloveds in to add fuel to the fire. Kimmel brought his wife, Molly McNearney, on to speak her mind, and Colbert brought WWHL host Andy Cohen on in as a Times Square Elmo. (It made sense in context, I assure you.) Rounding out the navel-gazing, perennial late-night guest (and one-time late-night host — that show was fun) Pete Holmes slammed late night as a dying medium. Yes and no, Pete. Is NBC defunding The Tonight Show? Yes. But is chat more central to the culture than ever, thanks to the phenomenon of podcasts on YouTube? Also yes.

Then on Late Night With Seth Meyers, the show became a teaser for the SNL50 celebrations. Will Ferrell and Harper Steele guested, discussing a post-9/11 barbecue at Steve Higgins’s house. My favorite sketch of all time, “Hamm and Bublé,” was discussed, and even Wally the cue-card guy got screen time during Thursday’s “A Closer Look.” Completely unrelated, but did you know that on Wally’s Wikipedia page, his birth date is “1965 or 1966”? What’s that about? Anyway, here are the funniest clips on late night this week.

5. Unpacking Panel-Show Trauma on After Midnight

After Midnight has both enlarged and shortened the talk-show segment of its programming, and I lament both changes. The tiny couch Taylor Tomlinson used to pull out has been replaced by a big couch, which is a bummer for fans of prop comedy. And now only one guest gets a deep question to tackle before launching into another game, which is a shame. The weird talk-show moments were some of my favorites of After Midnight — like this one where Tomlinson and Jade Catta-Preta trauma-dumped on the audience about how weirdly high-stakes it is to judge Is It Cake? It was a good moment of showbiz transparency, and I loved it.

4. Don’t Fuck With Molly McNearney

The swag of McNearney as she appeared on her husband’s show with her fucking Emmy, telling off Donald Trump for being a misogynist and a creep and a poor television critic. She was there to respond to Trump’s recent comments about how bad of a host Kimmel was of the Oscars earlier this year. (Like, way earlier.) It was a weird thing to bring up again in September. Point is: I am scared of Jimmy Kimmel’s wife, which I think both she and Kimmel know is a compliment of the highest order.

3. Prince Harry’s Most Challenging Mission Yet

Prince Harry has been through some stuff: war, losing his mother very young, interrogation training that went way too personal and disrespectful towards Princess Diana, that time he went to the Arctic and got frostbite on his dick. But he’s never had to strap a GoPro to his ass and walk through a maze. This was bonkers. How did they choose Harry as the celeb to do the Ellen-style Tonightmares walkthrough? Why not Tim Cook, who also did spon-con on The Tonight Show earlier this week? Why not Shaq, who had a haunt of his own (RIP Shaqtoberfest)? This was an incredible moment of guest meeting stunt — hats off to the Tonight Show booker.

2. A Devastating Read of Pete Holmes

After Midnight provided a fun “don’t react” game for panelists Jessica McKenna, Pete Holmes, and Echo Kellum called “Night Terrors!” Each participant laid on a bed that was 80 percent LCD screen and had to not laugh or scream as the other two said things to make them break, and Holmes broke after the first thing McKenna said! To be fair, it was one of the best reads of Holmes I’ve ever heard: “Pete, this is the longest you have been quiet with a camera facing you. Are you alive?” Got his ass! And he loved it, and we loved to see him love it.

1. The Two Faces of Andy Samberg on Late Night

Okay, let’s get the unpleasantness out of the way first: In the “French Pole Vaulter With a Giant Dong” sketch, Andy Samberg asks if this sketch will “win late night” on Vulture Dot Com. Well, Andy, I can’t be bought with a shout-out. But I also cannot look away from these two segments just because acknowledgment of this column makes me deeply uncomfortable. It’s the pairing of the sincere attempt to discuss Lee (the very serious movie Samberg co-stars in with Kate Winslet about war correspondents in the Holocaust) with the horrible, horrible dick puns that won late night this week. It’s how uncomfortable Samberg is trying to be sincere, combined with how much he clearly wants to be sincere, combined with abandoning that endeavor after the commercial break that makes this late-night gold.