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Robert Smigel on the sketch "In the Year 2000" that he wrote for Late Night with Conan O'Brien and on the inspiration coming from 60s television shows like The Jetsons; on the Clutch Cargo sketches which involved cutting out out lips from a still photograph and re-enacting the mouth through the photo (it was Smigel’s mouth); on his impressions being more "impercisions" than impressions of famous people like President Bill Clinton

Robert Smigel on having Adam West as a guest on Late Night with Conan O’Brien, and on other bits he came up with for West

Robert Smigel on Andy Richter and how the role of a sidekick for Conan on Late Night with Conan O'Brien came about; on how Richter was originally hired as a writer; on why it clicked between Conan and Andy; on how Stephen Colbert was also considered as Conan’s sidekick; on how NBC hated Andy as a sidekick initially; on what made a good sidekick for a personality like Conan’s

Robert Smigel on what made the Clutch Cargo sketches work on Late Night with Conan O'Brien; on his Arnold Schwarzenegger Clutch Cargo impersonation; on Arnold reminding him of Desi Arnaz

Robert Smigel on the stresses of producing Late Night with Conan O'Brien; on some of the challenges he faced as a producer; on his self-effacing personal style; on discontinuing "fake guests" on the show; on Don Ohlemeyer being a big supporter of the show; on a fake guest bit he did with Conan writer Louis C.K. about fake dog trainers; on this being the first time he did the dog-voice (a precursor to Smigel's "Triumph the Insult Comic Dog" character); on the genesis of his puppet character "Triumph the Insult Comic Dog" when he was producing Late Night with Conan O'Brien; on "Triumph" first uttering the phrase “for me to poop on”; on the dog’s gold bow tie and cigar; on the cigar prop; on doing a deadpan stare as "Triumph" in the vein of comedian Myron Cohen; on "Triumph" being able to do what Conan couldn't as a "nice host"; on the popularity of "Triumph"; on doing the first remote shoot with "Triumph" character at the Westminster Dog Show and how they were able to sneak into the show which did not want them filming there; on improvising the remote bits with "Triumph"; on being invited onto Hollywood Squares as "Triumph"; on going to a Bon Jovi concert; on "Triumph" filming the sketch outside a Star Wars movie premiere in New York City

Robert Smigel on the never-aired pilot he produced with Conan O'Brien called Lookwell, starring Adam West of Batman-fame

Robert Smigel on why he left Late Night with Conan O'Brien, and on what made that show unique