Fans already know that Colbert will play the fictional late-night TV host Scotty Bristol in the highly-anticipated season premiere. His on-screen sidekick will be played by Andy Richter of Conan (and Dancing with the Stars) fame.

And that’s not all. Colbert will also be joined by Amy Sedaris, playing Scotty Bristol’s head writer. It’s another collaboration between Colbert and Sedaris, but one that left the Late Show host feeling wildly uncomfortable.

“And also, the hardest part for me is that at one point Amy Sedaris, who I have known since I was 24, she’s like my sister. She seduces me at one point. That was truly upsetting,” Colbert said during an interview with Elsbeth star Carrie Preston.

The comment points to one of the more interesting parts of Colbert’s guest spot. The two first met in the Chicago comedy scene and went on to star together in Comedy Central’s Exit 57, a short-lived but beloved sketch series that highlighted their shared appreciation for the absurd. Over the decades, they’ve crossed paths in countless projects, from Strangers with Candy to guest spots on each other’s shows. Their friendship has been constant, with both frequently describing the other as family.

Colbert’s timing on the project also carries added weight. He filmed his appearance just a week after CBS announced that The Late Show would end in May 2026, abruptly ending his tenure in late-night television. Instead of retreating from the network spotlight, Colbert jumped into a scripted role that will undoubtedly surprise fans, even if the role isn’t too far from reality.

The result won’t be revealed until the October 12 premiere, but Colbert’s comments suggest viewers can expect discomfort, comedy, and a few shocking twists. His reunion with Sedaris alone makes the episode worth watching, while the timing of his late-night exit gives it an added layer of significance. For Colbert, stepping into Elsbeth is more than just a guest role, but a chance to show what else he can do on television.