The Lost Roles of Stephen Colbert

“Lost Roles” is a weekly column taking a different actor, comedian, or writer each week and examining all of the movies and TV shows they almost made but didn’t, for one reason or another. This week, we turn our attention to beloved newsman Stephen Colbert.

Before becoming a correspondent on The Daily Show (under original host Craig Kilborn) in 1997, Stephen Colbert spent a decade as a wildly funny performer at Second City Chicago who wasn’t getting the amount of career attention he deserved, being passed over for numerous big jobs. The Daily Show was Colbert’s big break, but it wasn’t until Jon Stewart took over as host that Colbert and the show really started to hit their strides. After spending eight years on The Daily Show, Colbert was finally given his own series. There, he quickly proved he was capable of anchoring his own show and achieved national treasure status. Let’s take a look back at some of Colbert’s earlier career attempts that didn’t work out, like auditioning for Saturday Night Live, writing movies, and serving as an on-air correspondent for Good Morning America:

1. Saturday Night Live (1992)

In a 2011 oral history of The Dana Carvey Show for GQ, Stephen Colbert revealed that he had tried out for SNL during a showcase for the show’s writers and producers at Second City Chicago. Colbert, who was Steve Carell’s Second City understudy at the time, recalls, “Robert Smigel had seen me perform at Second City when he was one of the people scouting for Saturday Night Live. When was Carvey? 1996? So that was in 1992 and I didn’t get hired for SNL that time.” While Colbert didn’t get an SNL job, he did impress Robert Smigel, who tells GQ, “Colbert completely blew me away. I was all about the understudy. Like, ‘Who’s the understudy?’”

Smigel ended up hiring Colbert as a cast member and writer for The Dana Carvey Show a few years later. When ABC canceled Carvey Show, Colbert briefly served as a writer on SNL in the fall of 1996. He even managed to make it on camera in small parts in a few sketches (like in the commercial parody below). Although he never was hired onto the cast, Colbert made a significant SNL contribution in voicing one of the title characters alongside frequent collaborator Steve Carell in the animated “Ambiguously Gay Duo” sketches, which Smigel created for Carvey Show and brought to SNL. Colbert even co-wrote some of these and other “TV Funhouse” sketches with Smigel during his Daily Show tenure in the late ‘90s and early ‘00s.

2. Late Night with Conan O’Brien (1993)

Robert Smigel also tried to get Stephen Colbert hired as a writer/performer on Late Night with Conan O’Brien when the show was starting up in 1993. Colbert explains, “Robert brought Conan to meet me. Conan came to the show [at Second City]. We met at a bar, the Old Town Ale House, had a couple of beers, talked, I submitted some jokes—and didn’t get hired.” Conan hired a lot of Second City guys as writers/performers, like Jon Glaser or Brian Stack, and it’s easy to imagine a young Stephen Colbert finding the same success on the show. Unfortunately, according to Smigel, “Conan didn’t quite see how Colbert could fit in.”

3. Good Morning America (1997)

After Carvey Show’s cancellation, Stephen Colbert took a job as an on-air correspondent at ABC’s Good Morning America. Colbert had a short stint there and only one of his reports aired before he moved on.  Here’s Colbert talking about this strange phase in his career to Media Bistro:

I desperately needed a job. I had been working for ABC Entertainment at The Dana Carvey Show in 1996. That show got canceled, my wife wasn’t working, and we had a baby. Someone from entertainment division recommended to the news division that if they were looking for somebody who was funny but looked really straight, for a correspondent for Good Morning America, that they should consider me. So I had a meeting with the head of ABC News—whoever it was at the time, in 1996, I wasn’t that cognizant of the news. They asked me if I could do it, I said yes, and they hired me. I did exactly two reports … Only one of which ever made it to air … After those two reports, I pitched 20 stories in a row that got shot down. At the same time, my agent, who also represented the executive producer of The Daily Show, Madeline Smithberg, said, “You should meet with Madeline. She’s doing this other show and I bet that they would do those stories.” And I went and met Madeline and the people at the show at the time, and they liked my ideas.

Here’s Colbert’s only Good Morning America appearance, about Rube Goldberg machines:

4. An “Ambiguously Gay Duo” Movie (2000)

Robert Smigel and Stephen Colbert wrote a script together for a live-action movie based on Smigel’s recurring animated SNL sketch “The Ambiguously Gay Duo.” Smigel explains to The AV Club that, although Colbert and Steve Carell voiced the characters in the shorts, he couldn’t use them on camera in the lead roles in the movie because they weren’t famous yet:

Carell and Colbert were, you know, it was the year 2000, and they weren’t superstars. Nobody had any idea. They blew us away at The Dana Carvey Show and we thought that they should have incredible careers, but we were surprised that they weren’t famous even then. We were surprised that Saturday Night Live hadn’t hired them back in 1996. Because they were both like 30 years old already, and they’d been around Second City.

And here’s Smigel talking about what the movie was:

Every successful character on Saturday Night Live prompts the question, “Is this a movie?” Ace and Gary were two characters I had no interest in doing a movie about. When I thought of them doing it live-action though, I thought, okay, I can make the characters much more dimensional, and, boy, would they look funny in those costumes with the enormous packages … I thought that would bring a whole new life to it and it would be a way of parodying the superhero genre without doing a movie that was just a superhero movie … You just want to see that car, and Colbert and I ended up writing a pretty crazy movie. It had a lot of satirical—Ace and Gary are big characters in it but there’s also enormous time spent with this rogues gallery and the government as well. We ended up getting to do a lot of funny social commentary about people’s attitudes about sexuality. I confess to still thinking about that one now and then. It was a very funny screenplay that we worked hard on and I know Colbert really liked it at the time before he became a national treasure. Now he’s like, “Ambiguously what?”

5. Trifecta (2000)

While splitting his time between The Daily Show and fellow Comedy Central series Strangers with Candy, Stephen Colbert sold a script for a movie called Trifecta he wrote with his Second City/Strangers with Candy collaborators Paul Dinello and Dave Pasquesi in 2000. Colbert, Dinello, and Pasquesi were all planning on starring in Trifecta, with Amy Sedaris also set for a big part and Dinello to direct. According to Variety, the movie  follows “two hapless brothers who break away from their boring lives and join forces with a psychotic conspiracy theorist. The trio then plans an ATM heist that ends up going haywire.” Like most movie projects, Trifecta unfortunately never made it through Hollywood’s grueling development process and remains unproduced.

6. Pioneer Town (2002)

Pioneer Town is a script that Paul Dinello and Stephen Colbert wrote for Dinello to direct. Dinello tells a fan site, “We were pitching [Trifecta] around and then I decided I didn’t like it. So I quickly wrote another script, based on an idea about a job that one of the characters in Trifecta mentions briefly. She says she works at Pioneer Town. I loved the idea of working at Pioneer Town that I wrote a whole script based on that idea.” Dinello explained that the movie is “about a guy who works at an American Settler theme park and is upset when a corporation takes over with plans to update it.” He was hoping to shoot it in the summer of 2006, but things didn’t come together.

7. An Untitled NBC Sitcom Pilot (2002)

Executive produced by Ron Howard and Brian Grazer via their company Imagine Entertainment, this was a comedy pilot for the 2002-03 TV season that focused on the work and family life of a TV news producer (played by Colbert). The pilot was written and directed by Ken Finkleman, creator of the acclaimed Canadian series The Newsroom, and Judy Greer co-starred, presumably as Colbert’s wife. NBC chose to not pick up the series and instead selected a trio of short-lived new comedies – Hidden Hills, In-Laws, and Good Morning, Miami – for its fall lineup

8. Another Untitled NBC Sitcom Pilot (2003)

The following season, NBC signed Stephen Colbert and Jon Stewart to write a pilot together as a starring vehicle for Colbert. The show was to be loosely based on Colbert’s experiences growing up in South Carolina, but it doesn’t look like NBC ever ordered the script to pilot. All for the best because if Colbert had starred in an NBC sitcom, he probably never would have ended up creating The Colbert Report.

The Lost Roles of Stephen Colbert