The funny thing about David Letterman announcing his retirement and CBS responding a week later by revealing that Stephen Colbert would take over The Late Show is this: it was sort of like they’d hired an unknown, considering America doesn’t have much of an idea who Stephen Colbert the guy is, since he’s always been performing through several layers of comedy. (The confusion wasn’t unlike what happened when the world first heard about a tall, geeky redheaded comedy writer by the name of Conan O’Brien.) Even when Colbert was starting out, he was performing in shows like Strangers With Candy with Amy Sedaris, another comedian who loves to put a good costume and several meta-layers of comedy between the audience and “herself.”
While we will miss the high-wire act that is “Stephen Colbert,” blowhard right-wing parody host of The Colbert Report (hopefully somebody — the who is still a mystery — will be around to keep 2016’s presidential election funny), when Stephen Colbert came out last night on David Letterman’s show, we got to meet a guy who is very well equipped to be one of the great talk show hosts. The key with a late-night host, is, of course, that you’re ostensibly yourself and it’s an intimate, fun backyard barbecue of a show, just some folks hanging out. And meeting Stephen Colbert — Northwestern grad, South Carolina native — was a gas.
Looking handsome in a lovely, different pair of glasses (Warby Parkers, maybe?), Colbert told Letterman that he came very close to taking an internship on his show in 1986, a classic “oh, I just tagged along with someone story” where he snatched the offer out of the hands of his then-girlfriend with sheer charm. (He was pretty foxy!) About ten years later, he was applying for a writing job with his partner Paul Dinello, and Colbert read from their Top Ten list sample: Top 10 Cocktails for Santa. “Scrooge Driver: Grain alcohol and regret.” But the Letterman show didn’t get back to the writers for four months, and by then, Strangers With Candy was getting started on Comedy Central. The appearance was enough to make the prospect of spending time on the Late Show With Stephen Colbert next year even more exciting.
Check out the full interview below: