At first, The Colbert Report did not seem a likely success. Sure, the eponymous host was funny as a correspondent on The Daily Show, but could his bizarro world Bill O’Reilly possibly work as the host of a nightly series? Not only did the show end up working, it launched Stephen Colbert as an arch comedic force, scoring a cluster of Emmys and bestselling books in the process. Colbert couldn’t remain in character forever, though, and now he’s ditching the blowhard persona in perhaps the best way possible: by taking over for David Letterman.
Though he seems like a natural choice now to fill the forthcoming Late Show void, after proving his enduring late-night appeal over nearly a decade of Report, Colbert had a long, winding road to get there. Here’s a look at all the formative stops he took along the way.
Exit 57, 1995
Colbert first began his fruitful relationship with Comedy Central in the sketch show, Exit 57, which ran for a single season in the mid-90s. It was the first major project he collaborated on with his creative partners Amy Sedaris and Paul Dinero, and it was typically wacky.
The Dana Carvey Show, 1996
The writers room on The Dana Carvey Show was stocked with future superstars like Louis C.K., Steve Carrell, and Charlie Kaufman, in addition to Colbert. Of course it was promptly cancelled. In the clip below, however, you can see Colbert getting comfy behind a desk, foreshadowing his future.
Good Morning America, 1997
When he wasn’t making short-lived TV shows, Colbert spent part of his time appearing in short comedy bits on Good Morning America that play, in retrospect, like an audition for The Daily Show.
The Daily Show, 1998
It’s hard to believe now, but there was once a Daily Show that didn’t have Jon Stewart. The now-seldom seen Craig Kilborn was the host in the show’s original conception, and Stephen Colbert actually beat Stewart to the punch by appearing on that version.
Strangers With Candy, 1999
The second major project Colbert made with cohorts Sedaris and Dinello proved to be their most popular. Strangers With Candy was a satire of after school specials wherein Sedaris played Jerri Blank, a 46-year old ex-con/high school student. Eventually, the show spawned a movie and a lot of famous friends pitched in with cameos.
Saturday Night Live
Occasionally during this time, Colbert would appear on Saturday Night Live in vocal form with the animated gay panic parody, The Ambiguously Gay Duo. he worked on these segments with Robert Smigel and Steve Carrell, comprising a partial reunion of the gang from The Dana Carvey Show.
The Colbert Report, 2005
The show that made Bill O’Reilly seem (even more) ridiculous has occasionally included high-profile musical guests like Arcade Fire and Daft Punk, making it a solid training ground for hosting a late night talk show.
White House Correspondents Dinner, 2006
What helped The Colbert Report break through to a more mainstream audience, though, was its host’s gutsy, hilarious speech at the 2006 White House Correspondents Dinner. Never before had a sitting U.S. president endure such a well-crafted, sly lambasting in person.
The Late Show With David Letterman, 2013
One way to prepare for sitting at Letterman’s desk is sitting on his couch, which Colbert has done many times over the years. Here’s the most recent.
The Hobbit: The Desolation of Smaug, 2013
Okay, so maybe a very brief cameo in The Hobbit did not help Colbert prepare to succeed Letterman, but we couldn’t resist including it.
What’s your favorite Colbert moment? Weigh in below in the comments.