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Failed Conan O'Brien writer Stephen Colbert is re-interviewed on The Late Show

Stephen Colbert, Conan O’Brien
Screenshot: The Late Show

Stephen Colbert occasionally likes to flip the late-night script and get interviewed himself on his Friday shows, taking the guest chair and having his illustrious and game would-be guests ask him some questions for a change. Invariably, there’s a good deal of goofing going on with the bit, although Colbert keeps accidentally revealing the sort of sincerely lovely anecdotes about himself that you’d expect from someone so widely liked in the industry (if not the White House). But with Conan O’Brien behind his desk on Friday’s show, things went predictably silly, with Conan doing shtick by first introducing Colbert (said with the hard ‘T’) as the guy who’d been rejected as a writer for Late Night With Conan O’Brien back in 1993.

Colbert, nervously shifting in his seat at the big opportunity to redeem himself, tried some flattery first, with O’Brien snapping into his imperious big-time asshole mode and asking icily, “Who the hell do you think you are?” Okay, bad start, although Colbert quickly opened up as he’s wont to do, explaining that, as a performer, he’s prone to depression and loneliness that only an audience’s applause can tamp down, for a while. “What’s that like, to be a needy performer?,” deadpanned Conan, “Who’s only happy when they’re getting laughs and, without it, they feel shallow and empty?” Segueing into shop talk, O’Brien shared the revelation his father had while watching Conan perform once, “You’ve taken something that should be treated and turned it into an occupation.”

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Speaking of occupations, the pair did touch on how Colbert wasn’t hired for Conan’s first late-night gig, a potentially awkward conversation turned immediately chummy, funny, and, yes, even a little lovely. Colbert, telling Conan that he and wife Evelyn McGee-Colbert have been married for 25 years, related a recent story involving the young long-distance couple’s early love letters (where they no doubt cursed out that gangly red-headed punk for not hiring Colbert), an innocent lie involving O’Brien, and the seeming butterfly effect that may or may not have led to O’Brien changing Conan’s format not long ago. Great story, although Conan was noncommittal about Colbert’s prospects for future employment on Team Coco. Still, O’Brien was encouraging, telling his guest, with a ruefully maniacal laugh, “You’ll get a gig—Network’s easy.”

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Dennis Perkins

Contributor, The A.V. Club. Danny Peary's Cult Movies books are mostly to blame.