With friends on SNL, Richter attended after-show parties, where he met SNL writer Robert Smigel. Two years later, Smigel hired Richter as a writer for a new show he was producing, Late Night with Conan O'Brien. Smigel sent Richter to join Conan O'Brien on stage during a practice run-through when the production staff was testing lighting angles and sound, and noticed the two had a strong rapport. He became O'Brien's sidekick just weeks before the show began airing in 1993. Richter departed from Late Night after the show on May 26, 2000. He later said of the decision, "After seven years of being on the show, I got itchy. I have a philosophy that if you enjoy good fortune, rather than sit there and say, "Oh, that's fine, this amount is good enough for me," you should try and push it. You should see how much you can stretch your good fortune. And I was curious." After Late Night Richter left his post at Late Night in 2000 to pursue a career acting in films and television. His first major venture, Fox's Andy Richter Controls the Universe, was canceled after two mid-season runs. His next Fox sitcom, Quintuplets, lasted one season. His 2007 television series, Andy Barker P.I., was co-written and executive produced by Conan O'Brien. In the series, Richter played an accountant who could not attract clients. After a woman comes to his office thinking he is the former tenant, a private investigator, she asks him to find her husband, who she thinks faked his death. Barker decides to pursue this job and becomes a private detective in earnest, and continues to do his accounting job, which seems to pick up as the series goes on. The series aired on NBC, with all six episodes in the first season on NBC.com. The series was canceled after very poor ratings, despite being named by Entertainment Weekly as one of the Top Ten Shows of 2007. The Tonight Show On February 24, 2009, it was announced that Richter would rejoin O'Brien as the announcer for The Tonight Show with Conan O'Brien in Los Angeles. Richter frequently appeared in comedy sketches on the show and often commented and interacted with Conan during the opening monologue; he was also part of the show's writing staff. In mid-December 2009, Richter also began joining Conan on the couch during the celebrity interviews, much like he