On Monday’s Late Show with Stephen Colbert, the audience got more than just laughs. Conan O’Brien, the veteran redhead who has weathered some of the most notorious battles in late-night history, sat down with Colbert for an extended 22-minute conversation. What began as a humorous retelling of a fake “advice dinner” ended up spotlighting the solidarity, vulnerability, and resilience of a genre under fire.

Conan the Survivor

Conan O’Brien’s career arc makes him uniquely suited to weigh in on Colbert’s precarious position.

1993: O’Brien replaced David Letterman on Late Night, surviving brutal early reviews and carving out a cult audience.

2009: He inherited The Tonight Show from Jay Leno, only to be forced out less than a year later when NBC reversed course and reinstated Leno.

2010–2021: He hosted Conan on TBS, proving he could thrive outside the broadcast mainstream.

2021–present: O’Brien has reinvented himself as a podcaster, producer, and occasional actor, with his Conan O’Brien Needs a Friend podcast ranking among the most popular in the world.

That résumé — particularly the 2010 “Late Night Wars” — gave his appearance alongside Colbert a sense of déjà vu.

“Cowardice Is the Way”

With Colbert facing the end of The Late Show in 2026, Conan recounted a (fictional) farewell dinner he once staged for his peers.

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

Colbert laughed, acknowledging the irony: both he and Jimmy Kimmel have been punished precisely for speaking truth to power. O’Brien pushed the bit further, joking that in 28 years he “never read the news” and “didn’t even know who was president.”

The exaggeration masked a serious point. Late-night has become a flashpoint in 2025, with hosts punished or sidelined for political satire. O’Brien’s “cowardice” advice was satire about satire: in the current climate, blunt honesty can be costly.

From NBC to Paramount: A Tale of Two Eras

O’Brien’s Tonight Show exit in 2010 was a corporate debacle: NBC mismanaged its transition plan, affiliates revolted over ratings, and Conan became collateral damage.

Colbert’s impending departure, by contrast, is shaped by corporate politics colliding with national politics. Parent company Paramount Global announced in July that The Late Show would end in May 2026, officially citing economics during its pending merger with Skydance. Yet the timing, paired with public pressure from FCC chair Brendan Carr and President Trump’s hostility toward Colbert, made the move look politically convenient.

Both stories highlight the fragility of hosts who, despite commanding loyal audiences, remain at the mercy of networks under pressure — whether from affiliates in 2010 or from regulators in 2025.

Conan Turns Sincere

After the jokes, Conan dropped into sincerity:

“I adore you. You’re a comedic force. I’m sad that this chapter is ending, but the connection you have with the audience, you’re taking with you. No one else owns that. That’s yours for the rest of your life.”

It was advice rooted in lived experience. O’Brien took his connection with fans from NBC to TBS to podcasts and tours. Colbert, he implied, will do the same, whether in scripted acting, producing, or another venture.

Solidarity in Late Night

The segment underscored a new dynamic: camaraderie. In 2010, O’Brien fought largely alone while Leno and Letterman looked on. Today, late-night hosts have rallied together.

Colbert has defended Jimmy Kimmel after his ABC suspension.

Seth Meyers has used his monologues to highlight threats to free speech.

Fallon, typically apolitical, even acknowledged Kimmel’s ordeal with a wink: “If you’re here for my suspension comments, you’ve got the wrong Jimmy… Dad.”

That solidarity matters in an era where political leaders have openly targeted hosts. It also provides a sense of cultural continuity as late night faces contraction: Colbert ending, Kimmel’s future uncertain, Fallon and Meyers under constant attack.

Conan’s Own Next Chapter

O’Brien wasn’t just on The Late Show to reminisce. He’s promoting his new film If I Had Legs I’d Kick You, a psychological thriller starring Rose Byrne, in which he plays her therapist. The project marks his first dramatic film role and opens Oct. 10.

That pivot mirrors what Colbert might embrace after 2026: scripted roles, film work, and projects outside the nightly grind.

The Broader Picture: Late-Night’s Precarious Moment

Colbert’s farewell is part of a larger trend. CBS is exiting late night altogether. ABC nearly lost Kimmel permanently after his suspension. NBC’s Tonight Show and Late Night are locked in carriage disputes with YouTube TV. The once-crowded field is shrinking fast.

The battles O’Brien once fought over time slots and affiliate ratings have given way to something more existential: whether political satire itself has a place on network TV in the Trump era.

Conclusion: From Jokes to Lessons

Conan O’Brien’s visit to The Late Show was a master class in comedy, but also in perspective. His mock advice — “cowardice is the way” — captured the absurdity of today’s risks for hosts. His real advice — that the bond with an audience is portable — was a reassurance to Colbert and his viewers alike.

As late night contracts under corporate and political pressure, Conan’s career stands as a reminder: hosts may lose time slots, but if they remain authentic, their audience will follow them anywhere.

For Colbert, whose run ends in 2026, that lesson may be the most valuable parting gift his fellow survivor could offer.