Way Back Machine

Watch Stephen Colbert's First Appearance on 'The Late Show With David Letterman'

It was in 2005, before The Colbert Report premiered. And he’s not in character!


Before Stephen Colbert was officially replacing David Letterman—it’s happening!—Stephen Colbert needed David Letterman.

Once upon a time, you see, The Colbert Report had not yet debuted, Stephen Colbert was not yet one of the country’s most beloved late-night personalities (and certainly was not yet entirely defined by the “Stephen Colbert” persona), and The Late Show was not yet a television dynasty with a host soon to abdicate his desk-throne. That time, to be exact, was fall 2005, when Stephen Colbert made his first appearance on The Late Show with David Letterman, the very show he would be announced as the new host of nine years later.

Back then, Colbert was just like any other star paying Letterman a visit, hoping that the appearance would drum up excitement for this little project of his he hoped could maybe one day turn into a very big deal.

Right off the bat, there’s something jarring about the interview to anyone who has turned watching The Colbert Report into a nightly ritual, or delighted in any of Colbert’s appearances at awards shows and on talk shows over the years. He’s not in character! Stephen Colbert is actually Stephen Colbert, not “Stephen Colbert,” regaling Letterman with stories of his upbringing in South Carolina as one of 11 siblings (each of whom he, in true “talk-show bit” fashion, breathlessly lists), his misadventures sailing, and imaginary boyfriends.

Speaking to Vulture Wednesday, just one day before Colbert was officially announced as the new Late Show host, Colbert’s friend Jon Stewart said that his Comedy Central colleague would be well-suited for the new CBS gig. “He’s done an amazing job with just that very narrow cast of character, but he’s got a lot more he can show,” Stewart said. “He’s got some skill sets that are really applicable, interviewing-wise, but also he’s a really, really good actor and also an excellent improvisational comedian. He’s also got great writing skills. He’s got a lot of the different capacities. Being able to expand upon [those] would be exciting."

This vintage Late Show appearance is an endearing walk down memory lane, especially with today’s big news, but it also proves Stewart’s point exactly. Out of character, Colbert retains the sharp wit, effortless delivery, knack for spinning a wacky-hilarious yarn, and keeping an easy presence as one-half of a late-night interview. All of the skills needed by the perfect Late Show host.

“Our first guest is a very talented man who will soon have his own television program,” Letterman says, introducing Colbert back in 2005. Just shy of a decade later that introduction remains true, but takes on a whole new meaning.