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The Dartmouth
May 3, 2024 | Latest Issue
The Dartmouth

From Chicago to NYC: Andy Richter's couch trip; With almost 1,000 episodes of 'Late Night with Conan o'Brien' wrapped, Richter discusses his rise to fame

Not too long ago, five years to be precise, David Letterman stepped down from his NBC post at "Late Night," and a newcomer, Conan O'Brien, took over. Alongside the redheaded host was Andy Richter, an actor turned writer turned sidekick. As the show's ratings improved, audience appreciation for Richter increased, and now as the show approaches its one thousandth episode on October 8, he has become a staple of late-night television.

However, being the late-night sidekick wasn't Richter's original plan in life. "When I got out of school, I started working freelance in film production," he explained in a recent interview with The Dartmouth. A graduate of Columbia College, Richter intended to break into the film business by becoming a production assistant and working with props.

"I started getting bored, so I started taking improv classes," he said. "That was too much fun to stop doing." His attraction to the improv scene wasn't purely coincidental. He had already experimented with acting in film school. "No film students know any actors," Richter said, and therefore many students needed to act in each other's films. Richter enjoyed his on-camera gigs and was requested frequently. A film school friend, Beth Cahill, knew of Richter's acting talents and urged him to do improv.

"I was always kind of curious ... I have a hard time focusing and the immediacy appealed to me. I've always worked best in groups," he said. Richter's improv career soon took off, and he became a member of "The Annoyance Theater" in Chicago where he and several others put on "The Real Life Brady Bunch." The show was hit, and when it moved to New York for a scheduled six-week run, the actor playing Mike Brady backed out, and Richter took his place.

With his acting career taking off, Richter moved out to Los Angeles where he hired an agent and pursued a film career, most notably with a role in "Cabin Boy." At the same time, Cahill joined the cast of "Saturday Night Live" where she met and worked with writer Robert Smigel. Cahill introduced Richter to Smigel and the two struck up a friendship.

After Letterman's departure from NBC, Smigel became the headwriter for "Late Night" and was influential to the show's recreation. Smigel then called up Richter and asked if he wanted to meet O'Brien. "I met with them at a deli and we hit it off," Richter recalled. "A week later I was here. I was sitting in this office and all these other offices were totally empty."

Originally hired as a writer, Smigel approached Richter to be a sidekick during one of the test shows. "My first reaction was 'Ugh' just because I thought the sidekick was the guy that laughed at everyone else. Then I thought ... who am I to turn down being on TV every night?" Richter said.

The chemistry worked, and when "Late Night with Conan O'Brien" aired in 1993, Richter was the official sidekick of the show. At first, the show received a critical thrashing. Several reviewers targeted Richter for being one of the main problems of the show.

"Don't get me wrong, it's annoying when someone refers to you as 'chubby' or 'fat'...It all becomes sort of absurd and meaningless, and what is meaningful is the fact that you are coming into a workplace everyday and trying to do a good job. I have the ability to divorce myself from anxieties that aren't useful."

Despite negative reviews, Richter remained at his post, and, along with the other writers, pulled 13 to 14 hour days. "I was as much a writer as anybody," he claimed, but after three years, when the show started finding some security in NBC, Richter essentially stopped writing. "The show will go on if I go home at 8:30 instead of 1:30," he said. Richter also noted the vested interest the entire show had in making sure he didn't burn out and become unhappy with his job.

Surprisingly enough, for the first few months of the show, Richter and O'Brien rarely spoke outside of the show. This wasn't because of any animosity, but because of the intense pressure being put on O'Brien during those first months. "He was so much under the gun that he was just trying to learn how to talk to celebrities and tell monologue jokes and being in charge of a talk show," Richter said.

A year and a half after the show started, Smigel stepped down as head writer and ushered in a new working relationship between O'Brien and Richter. "When you are doing a comedy show, you need to have somebody you can turn to that you trust. Someone you can ask, is that funny?...Robert was that for Conan. When he left, I kind of stepped into that role." As a result, the two began working together more often and forging a strong backstage relationship.

Luckily, there aren't many artistic conflicts between the two hosts. "It's his show and things go his way, and they should, and I had no problem realizing that there's not just one way to be funny...You can't treat every one [joke] as an artistic jihad."

Still, while the show has changed Richter's life for the better ("I have more money," Richter happily stated) and vastly boosted his career, he views it as a fun excursion, not the pinnacle of his life. After all, his original plan when he moved out to Los Angeles was to become an actor in film or television. "This has been a wonderful side-trip, but I still in my mind feel like I'm going to get back to that point in my life." Nevertheless, Richter has been more than happy with his "Late Night" position. "It's done wonders for me professionally and personally just in terms of my own education as a show business 'professional.'" And how much has Richter changed? "I think beyond my next meal now."