They say that hindsight is 20/20, and during his latest stop on The Late Show with Stephen Colbert, former late-night host Conan O'Brien revealed just how accurate that saying can be. No stranger to late-night conflict himself, O'Brien once shared some sage advice with Colbert and his other fellow hosts on how to remain on the air without ruffling any feathers.
Of course, O'Brien's tenure as a late-night host began over 30 years ago when he began hosting Late Night with Conan O'Brien, taking over for David Letterman, who moved to The Late Show. In 2009, O'Brien took over The Tonight Show from Jay Leno, but after less than one year, NBC announced plans to bring Leno back to late night, leading O'Brien to host Conan on TBS for 11 years.
While the circumstances surrounding Colbert's current situation with Paramount are different, the results are similar. Colbert will sign off the air in May 2026 after a highly publicized dispute with Paramount following its merger with Skydance. Jimmy Kimmel also recently returned from a shocking suspension by Disney after a political conflict drew immediate criticism on both sides.
Conan O'Brien once warned Stephen Colbert not to "speak truth to power"
As late-night shows and their hosts find themselves in precarious territory under the current presidential administration, there's a lot of conversation happening among fans and even more camaraderie happening between each of the long-tenured hosts. O'Brien dropped by Colbert's show on Tuesday, Sept. 29 for a 22-minute extended interview and shared a humorous story about the wisdom he once offered his pals after leaving late night.
"Just as I was leaving my late-night show, I took you and all the other late-night hosts out. Remember this? 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.’ I said, ‘Don’t do anything to ruffle any feathers.’ Remember? I said that. And I said, ‘Whatever you do, don’t speak truth to power.’ I said, ‘Cowardice is the way,'" O'Brien playfully joked with Colbert.
O'Brien continued his joke-laden story by stating that in his 28 years hosting Late Night, The Tonight Show, and Conan, he "never read the news" and "didn't even know who was president." Obviously, that's not true, as he's simply over-exaggerating how bipartisan late-night hosts seem to have to be these days lest they get yanked off the air for any minor infraction.
After his hilarious retelling of his advice, O'Brien gushed over his friend with all seriousness, telling him that he adores Colbert and views him as a comedic force. Like all of us, he's "sad that this chapter is ending," but he expressed his excitement for all the greatness that's to come in the future for Colbert in the next chapter.
As O'Brien knows best, an audience follows the talent: "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."
Even though it's nice to see all of the late-night hosts being there for each other in this moment (Kimmel and Colbert will also have a crossover this week), O'Brien wasn't only on the show to show support for his friend. He's promoting his new movie If I Had Legs I'd Kick You, a psychological thriller starring Rose Byrne in which he plays her character's therapist. The film marks his dramatic acting film debut and hits theaters on Oct. 10.