This week sees Stephen Colbert ascend to new heights of fame, but some of his greatest work wasn’t so mainstream…
It feels like just yesterday we were saying goodbye to David Letterman, and now we’re already at the start of The Late Show With Stephen Colbert. After years as Comedy Central’s late night satirist, Colbert is now going network just as the medium of talk shows is feeling more ancient than ever. But as longtime fans know, Colbert’s infectious comic energy can make anything feel alive and worthwhile, even staid talk shows. Fans who’ve been following him for two decades know this especially well.
Look, I’m not trying to play the hipster card of “I’ve been watching Stephen Colbert for more than 20 years” on all of you, but, seriously, I’ve been watching Stephen Colbert for more than 20 years. To see him go from underappreciate costar of an underwatched satire to inheriting the desk of David-freaking-Letterman is a pretty big deal. And when you explored all his best moments that lead him to this newfound level of success, you’d appreciate it all the more.
So, let’s take a look, in chronological order, of all the great projects Colbert appeared in. Many of these come from long before he became to the ridiculous figure of conservative outrage that fueled his most famous appearances. This… is my report on Colbert…
When you look closely at Colbert’s career, it’s just about impossible to not also bring up two other able performers: Paul Dinello and Amy Sedaris. The trio, along with Mitch Rouse and Jodi Lennon, worked in Chicago sketch groups together before starting Exit 57, one of Comedy Central earliest original sketch shows. As the above scene will show you, it was weird, confrontational, and honestly a bit confounding to a live audience. No matter how obtuse the sketches may have been, Stephen’s skill as a performer is immediately obvious. Exit 57 was early work by creative folks who’d go on to so much more. However, if you were one of the sad sacks watching Comedy Central all day in 1995 – like Waylon Smithers and myself – it was an early glimpse at a future star.
The Dana Carvey Show
This sketch show had Stephen Colbert, Steve Carell, Louis C.K., Robert Smigel, and Charlie Kaufman working with one of the most popular Saturday Night Live cast members ever. Despite all that, it’s remembered as one of the biggest failures in broadcast history, thanks to material that was far too weird for folks who just finished watching an episode of Home Improvement. Though it only last seven episode, Colbert was excellent as usual on this show, particularly when paired with Carell. Stephen would even start doing the type of faux news stories that he’d take with him to The Daily Show.
Strangers With Candy
For three seasons on Comedy Central, Strangers With Candy was one of the sharpest, meanest satires on TV, even many viewers failed to notice. Colbert once more teamed with Sedaris and Dinello, this time parodying after school specials of the 1970s, only the people involved never learned a single lesson. Sedaris was the star as the purposefully hideous Jerry Blank, while Colbert and Dinello played teachers Chuck Noblet and Geoffrey Jellineck respectively, two horrible teachers who were not so secretly having a romance. Colbert’s character could go from severe to pitiful in seconds, all played with straight-faced conviction throughout. The trio wrote and starred in the show until an abrupt cancellation in 2000, and it still feels pretty current if you pull it up on Hulu now, so get to watching it.
If you need more inspiration, how about a little song and dance?
Read on to see even more Colbert gems, including an overlooked book and all his work on Adult Swim!