Stephen Colbert’s Second City Memories Won Late Night This Week

by

It’s sad to think about the small bar hidden under Stephen Colbert’s desk – it will likely disappear when they renovate the Ed Sullivan Theater, and we should acknowledge it now! Colbert’s habit of offering guests a drink always felt natural and relaxed, never pushy. It was simply a way to help his guests feel comfortable, and they clearly appreciated it – Pedro Pascal was noticeably nervous until he received a small pour of tequila this week. It’s almost a ritual, offering a bit of ease to celebrities. Here’s a look at which stars handled their late-night appearances with the most poise this week.

5.
The Daily Show Says AI Is Not Your Friend

https://youtube.com/watch?v=VViY5rm-Y1Y?si=zNl5lhF0Xa048ve8

It’s hard to beat The Daily Show hilariously skewering ridiculous AI startups created for a niche audience. But The Daily Show doing it to two such startups? Even better. Ronny Chieng’s obvious disapproval was incredibly satisfying. He voiced what many of us feel: that AI is often pointless and can’t replace real human connection, and that the Empire is clearly the villain in Star Wars.

4.
WWHL Does Sally Field by the Numbers

https://youtube.com/watch?v=watch?v=TiWhJpe4cQ8

I was absolutely loving watching Sally Field on WWHL! She and Lisa Kudrow were just brilliant together all night. Lisa’s improv as Valerie Cherish was hilarious – it totally felt like something straight out of The Comeback. But honestly, the highlight for me was Sally just letting loose and not caring what anyone thought – even dropping an f-bomb on live television! It was so refreshing to see her be so wild and free, and I, for one, absolutely adored it. She was fantastic!

3.
Pedro Pascal Loves the Water

https://youtube.com/watch?v=watch?v=vBqMQ1LQ6B4

We mentioned Pascal’s appearance on Colbert briefly, but his segment on Seth Meyers was much funnier and made the top five. Meyers started by asking, “Are you one of those people who really loves the water?” – instantly creating a funny image of a certain type of person, someone who might pretend to be a mermaid in the pool even as an adult. Pascal playfully responded to this idea, sometimes embracing it and other times acting like it was as irritating as Meyers suggested. As someone who often talks about how much they enjoy the water, I felt both seen and understood by the bit.

2.
How Far (or Near) Will The Tonight Show Go?

https://youtube.com/watch?v=watch?v=sDa5YhO_EYk

Jimmy Fallon came up with a fun interview game for his chat with Jim Parsons, inspired by the movie Titanic. They played while Céline Dion’s song “My Heart Will Go On” was playing. Whenever Céline sang the word “near,” Jimmy and Jim had to move close together. If she sang “far,” they had to move as far apart as possible – and they really stretched the limits of the studio! It was a playful way to get moving during the interview.

1.
Second City Memories and Veep Dreams

https://youtube.com/watch?v=watch?v=qW_ixPW16ac

Everyone was talking about Julia Louis-Dreyfus playfully roasting Stephen Colbert while in character as Selina Meyer – it was hilarious! And yeah, the kiss got some attention, but honestly, Colbert’s been on a kissing spree lately, and good for him. But for me, the real magic happened when those two Second City veterans started chatting about Chicago. It reminded you of their shared history and comedic roots. When Colbert eventually steps down (and ugh, it’ll be too soon!), that’s what I’ll miss the most: seeing him connect with someone who truly gets comedy because they’ve lived it.

Read More

2026-05-15 18:54