Stephen Colbert’s 15 Funniest ‘Late Show’ Moments That Still Make Us Cry-Laugh

The Late Show with Stephen Colbert is coming to a close, leaving behind more than a decade of giggles and guffaws. From topical humor (often about whatever fresh Hell the United States government is bringing us on any given day) and silly celebrity sitdowns to nerding out over J.R.R. Tolkien, Stephen Colbert never failed to bring the belly laughs, even when it felt like the world—and at times his career—was up in flames.

Colbert’s cancellation was announced in July 2025, shocking comedy fans and the general public alike amid censorship fears and a merger between CBS’ parent company Paramount and Warner Bros.Discovery.

“I tried never to take for granted filming in the Ed Sullivan Broadway theater, having that tremendous audience, or having the ability to work with the funniest people I know every day and make jokes about the things that make me most anxious,” Colbert told PEOPLE. “It takes a lot of bone marrow to do the show every day, and now I’ll be stepping down with enough time, enough energy to do other things that I want to do.”

What he’ll miss most about the job is bringing joy and comfort to audiences.

“I hope they laughed. I hope they felt better at the end of the day,” he says. “I mean, that’s it. We’re there. We’re the last thing you see. A lot of things happen in a day, but we bat last, and so we get the last take that people hear before they go to bed, and I hope it made their day better.”

Oh, Stephen. It did. And you did.

Look back at Stephen Colbert’s funniest Late Show moments to laugh until you cry (and to laugh through your tears).

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Stephen Colbert’s Funniest ‘Late Show’ Moments Ahead of the Show’s May 21 Finale

15. “UNCUT: The Nicki Minaj Interview”

Before she decided to go publicly MAGA, Nicki Minaj got cheeky on The Late Show with Stephen Colbert and made the man blush (seriously, he is beet red here) and crack up like crazy.

Related: Stephen Colbert Loves This Ina Garten Chicken Recipe—After Trying It, I Can See Why

14. “This Monologue Goes Out to You, Mr. President”

Colbert channeled his inner POTUS No. 47 in a monologue directed at Donald Trump after Trump attacked journalist John Dickerson. When he attracted controversy afterward, Colbert responded in a subsequent episode, “Now, folks, if you saw my monologue on Monday, you know that I was a little upset at Donald Trump for insulting a friend of mine. So, at the end of that monologue, I had a few choice insults for the president in return. I don’t regret that. I believe he can take care of himself. I have jokes; he has the launch codes. So, it’s a fair fight.”

Related: CBS Announces Replacement for ‘The Late Show with Stephen Colbert’

13. “Taylor Swift’s Mood Board Proves ‘Hey Stephen’ Isn’t About Stephen Colbert”

Taylor Swift did a COVID-19 pandemic virtual appearance on The Late Show to promote Fearless (Taylor’s Version), in which she insisted that Colbert didn’t inspire the fan favorite track “Hey Stephen.” (Fun fact: The song is really about Stephen Barker Liles of Love and Theft.)

Related: Taylor Swift Shares Major Personal Revelation on ‘The Late Show With Stephen Colbert’

12. “Tea at the Plaza”

Aubrey Plaza and her signature deadpan delivery served tea to Colbert in October 2022 and dished on The White Lotus and her co-stars and coworkers throughout her career, including Joy Behar, Jennifer Coolidge, Elizabeth Olsen, Danny DeVito and more.

11. “Saoirse Ronan Tries to Teach Stephen an Irish Accent”

In January 2016, Saoirse Ronan tried to teach Colbert how to pronounce her first name, as well as the key elements of Irish accents—including the importance of pitch.

Related: Josh Brolin and Stephen Colbert’s Hilarious Bromance Steals the Show in Chaotic Interview

10. “Stephen Calls Bruce Willis a Liar … MISTAKE”

Bruce Willis appeared on The Late Show with Stephen Colbert in December 2015, and Colbert told the Die Hard star that he doubted he did his own stunts. That led the duo into a hilariously choreographed brawl (and rewatching it makes us miss them both terribly, as Willis’ battle with aphasia led him to leave the limelight).

Related: How Bruce Willis Is Still Saving the World 29 Years After ‘The Fifth Element’

9. “Ryan Gosling Takes the Colbert Questionert”

Ryan Gosling proved once again that he is as hilarious as he is hot when he took “The Colbert Questionert,” especially when it came to answers he didn’t want to provide. Even Colbert couldn’t keep a straight face for most of this.

Related: Ryan Gosling Could Buy a Barbie Dream House With His Net Worth in 2026

8. “Sir Anthony Hopkins, as Hannibal Lecter, Can Make Any Classic Movie Line Sound Terrifying”

Sir Anthony Hopkins stopped by The Late Show with Stephen Colbert for a Halloween episode, in which he made otherwise innocuous classic movie lines sound absolutely terrifying thanks by reciting them in character as Hannibal Lecter.

Related: 1991 Hit Horror Film, Widely Regarded Among Best Movies Ever, Returns for 35th Anniversary

7. “Trump or Colbert?”

Back when he was still running in the Republican presidential primary, Donald Trump was a relatively good sport when playing “Trump or Colbert,” in which he had to guess whether a quote was from himself or from Colbert’s Colbert Report character.

Related: Stephen Colbert’s ‘Unhinged’ 3-Word Response to Donald Trump’s Gloating Over ‘The Late Show’ Cancelation Ignites Fans

6. “Gordon Ramsay Critiques Stephen’s PB&J”

Gordon Ramsay cursed up a storm (of course) and reviewed Colbert’s peanut butter and jelly sandwich during a memorable segment on May 26, 2017. He was not gentle.

Related: Next-Level Spouse: Get to Know Gordon Ramsay’s Wife, Tana Ramsay

5. “InfoWars’ Alex Jones Has Nothing on Tuck Buckford”

Colbert skewered far-right conspiracy theorist Alex Jones and InfoWars as Tuck Buckford, who became a recurring character throughout his tenure on The Late Show.

Related: Stephen Colbert Reveals His Sister Was the ‘Deciding Factor’ in Hosting ‘The Late Show’

4. Lin-Manuel Miranda and Stephen Perform “Button!”

Lin-Manuel Miranda and Colbert took inspiration from Hamilton to perform “Button!,” which Colbert called a “one-song play” about a signer of the Declaration of Independence.

Related: Stephen Colbert Directly Calls Out CBS On ‘Late Show,’ Names Guest The Network Barred

3. “Stephen Is Become Death, Destroyer of Worlds”

Colbert sat down with Christopher Nolan to poke fun at the often self-serious Oscar winner, who was promoting Oppenheimer. The cold open was a killer and gave a rare peek at Nolan’s sense of humor.

Related: Christopher Nolan Causes a Stir After Casting Move with Popular Musician

2. “The LOTR Rap”

Colbert spit fire with Jon Batiste, Lord of the Rings stars Sean Astin, Billy Boyd, Dominic Monaghan, Orlando Bloom, Andy Serkis, Hugo Weaving and Elijah Wood, plus cameos from Anna Kendrick, Killer Mike and Method Man (because Ian McKellen wasn’t available) about his favorite franchise being “the No.1 trilly,” and it never gets old.

Related: 80 Best ‘Lord of the Rings’ Quotes to Inspire You to Live Your Most Heroic, Epic Life

1. “Wanton Destruction of CBS Property”

Revenge is a dish best served flying off of a rooftop: Colbert’s predecessor David Letterman joined him to essentially tell the network that shafted Colbert to shove it. Bless.

Related: Stephen Colbert’s Final ‘Late Show’ Week Has Fans Bracing for an Emotional Goodbye