Conan OBrien Jokes About Warning Stephen Colbert as The Late Show Faces Final Season

Conan O’Brien brought laughter, warmth, and reflection to “The Late Show With Stephen Colbert” on Monday night, revisiting advice he once gave to Colbert and reflecting on the end of an era in late-night television. His visit came at a pivotal time, as Colbert prepares to wrap up The Late Show in May 2026 following CBS’s decision to end the long-running program.

A tongue-in-cheek warning to late-night hosts

Opening the conversation, O’Brien recalled the moment four years ago when he stepped away from late night after nearly three decades. Before bowing out, he gathered Colbert and other hosts together for dinner.

“Remember this?” O’Brien teased. “I took you guys to a wonderful Sizzler restaurant. We all had our trays, and I told you, ‘Take care of late night. If you take care of late night, late night will take care of you.’ And then I said, ‘Don’t do anything to ruffle any feathers.’ Remember? And I said, ‘Whatever you do, don’t speak truth to power. Cowardice is the way!’”

The crowd erupted with laughter. O’Brien doubled down on his signature self-deprecation: “During my 28 years as a late-night host, I never read the news. I had a masturbating bear and a plastic dog. I didn’t even know who was president!”

Colbert, deadpan as ever, quipped back: “Thanks for being here, Conan.”

Humor with a heartfelt undertone

Beneath the humor, O’Brien also struck a sincere note, expressing admiration for Colbert both personally and professionally.

“Stephen, I adore you. I love you. I know you as a person and also as a comedic force. And like so many people, I’m very sad that this chapter is ending,” he said.

“But I also want to say—you’re going to do amazing things, and you’re going to have a lot of fun. The connection you have with the audience—and this goes for Kimmel, Fallon, all of you guys—it’s very special. That connection is something you carry with you. Nobody else owns that. That’s yours for the rest of your life.”

The moment offered a poignant contrast to the laughter earlier, highlighting the camaraderie between two of late night’s most influential figures.

Late night in turmoil

O’Brien’s guest appearance came during a period of unprecedented upheaval for late-night television. CBS’s decision to cancel The Late Show shocked viewers and marked the end of an important chapter in the genre.

At the same time, ABC’s Jimmy Kimmel Live! was briefly pulled from the air after Jimmy Kimmel’s controversial remarks about the assassination of Charlie Kirk. The move sparked heated debate about free speech, comedy’s role in political discourse, and how late-night hosts navigate sensitive topics.

Kimmel was reinstated last week after a six-day suspension. Colbert celebrated the news on his show with typical flair:
“Our long national late-night nightmare is over! Come on! Wonderful news for my dear friend Jimmy and his amazing staff.”

Conan’s legacy, Colbert’s future

Conan O’Brien’s career spans more than 28 years of late-night television, from Late Night With Conan O’Brien to The Tonight Show and later Conan on TBS. Known for his absurdist humor, self-mockery, and offbeat sketches, O’Brien created a unique comedic voice that blended intellectual wit with slapstick absurdity. His legacy is one of innovation and risk-taking in a format often constrained by tradition.

Stephen Colbert, meanwhile, has become one of the defining voices of the modern late-night era since taking over The Late Show in 2015. Unlike O’Brien, Colbert leaned heavily into politics, offering sharp monologues and satirical takes on current events. His willingness to “speak truth to power” made him a cultural force but also exposed him to controversy and scrutiny.

As The Late Show prepares to sign off, Colbert leaves behind a powerful body of work: incisive commentary, memorable interviews, and a blend of intellect and accessibility that redefined the late-night landscape for a generation.

A farewell to an era

The exchange between O’Brien and Colbert on Monday night served as both comic relief and heartfelt goodbye. For O’Brien, it was a chance to share wisdom—both in jest and in earnest—with someone about to face the same transition he did four years earlier.

And for Colbert, it was a reminder that while the show may end, the bond with his audience and the impact he has made will endure.

As O’Brien put it, closing out his remarks: ending a show is not the end of the journey—it’s simply the beginning of another chapter in a creative life.

📺 Fans can watch the full interview between Conan O’Brien and Stephen Colbert on the latest episode of The Late Show With Stephen Colbert.