The Late Show dropped a nice little surprise this week in the form of two “Flipped Interview” segments, where Stephen Colbert trades places with his guests and becomes the interviewee rather than interviewer. These new segments work particularly well because the interviewers are good friends of Colbert’s — first fellow is Daily Show alum John Oliver, and then the other is his former Strangers With Candy collaborator Amy Sedaris. (Both segments appear to be saved up from Oliver’s and Sedaris’s Late Show appearances from February.) Oliver takes his turn at the desk to ask Colbert a series of supposedly “classic first-date questions” he found online, which Colbert finds quite attractive. “You’re cute,” he tells Oliver during the segment. “Thank you,” Oliver responds. “You’re coming on a little strong, but I do like to be chased.” As is the case with any typical first date, the conversation includes Colbert predicting his own death, which involves a horrific contraption around his face where he’s forced to drink water as it fills over his face before inevitably drowning.
After that, Oliver asks Colbert what friendship has impacted him the most, and Colbert drops the reality hammer and gives a startlingly sweet, sincere answer. “My wife. Without a doubt. No one comes close. The most harrowing idea would be that I would spend any part of my life without her, because that would be a level of loneliness and irreplaceable, irredeemable emotional desolation that I could not possibly contemplate. And I understand why old men die like a month after their wives go, because how I will actually die is she will die first and I will not last a year,” he says. “Okay,” Oliver responds, “check please. I’m wasting my fucking time here.”
Sedaris’s segment with Colbert delves into their days performing comedy in Chicago and working together on Strangers With Candy. Colbert showers Sedaris with praise: “I like to tell people that writing for you was one of the proudest things I’ve ever done. You’re one of the funniest people on the planet, and to have written anything that you said was a real source of pride for me. I brag about it.” Sedaris then presents Colbert with a series of “trigger words,” which are really just reminders of different memories they made together with comedian Paul Dinello as they were in the early phase of their careers. For example, they look back on the time when Sedaris made Colbert laugh so hard while improvising onstage with her and Dinello that Colbert got pissed, stormed backstage, locked himself in the bathroom, and cried. “And you stood outside that bathroom door, and the two of you mocked me,” Colbert remembers, “and I realized in that room that you had broken something in me, and I came out a changed man … I came out and I was never as professional as I should be again.”