Robert Smigel on leaving Saturday Night Live; on Lorne Michaels wanting Conan O'Brien to produce the Late Night weekday slot first held by Steve Allen and later Jay Leno; on Lorne initially wanting Dana Carvey to host the show; on Conan O'Brien turning down producing the late-night show slot because he wanted to be an on-camera performer again; on Conan auditioning for Lorne Michaels to take over Late Night on Lorne's involvement with Conan's show Late Night with Conan O'Brien; on hiring Dino Stamatopoulos and Louis C.K. as writers on Late Night with Conan O'Brien; on Tom Brokaw's cameo on the show; on the first episode and the tone being very dark
21:10
Robert Smigel on the genesis of Late Night with Conan O'Brien; on wanting it to be the opposite of David Letterman’s style but invoking his name in the first episode; on wanting to go right to where the “stress” is in humor; on Tom Brokaw’s cameo on the show; on the very dark humor present in the first season of the Late Night show; on the "Actual Items" bit on the show
05:46
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
04:51
Robert Smigel on the genesis of the Conan sketch "Masturbating Bear" which Brian Reich developed; on the bear bit being funnier due to the limitations put on it by Standards & Practices
01:44
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
02:42
Robert Smigel on switching roles from writer to producer on Late Night with Conan O'Brien; on producing a five-day-a-week show; on the format of the show; on what Conan brought to the show's dynamic
04:16
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
06:30
Robert Smigel on the Clutch Cargo-style bits he and Dino Stamatopoulos devised for Late Night With Conan O"Brien (this technology consisted of a still photo image of a celebrity paired with a real person’s mouth voicing an impersonation of them); on how Smigel came to be the mouth on the Clutch Cargo sketches; on his impression of President Bill Clinton; on doing this sketch live being one of the most exciting moments in his career
04:05
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
02:14
Robert Smigel on his Bob Dole Clutch Cargo impression on Late Night with Conan O'Brien being his favorite; on talking about the Senator in the third person; on Dole being the funniest person he ever got to play; on doing a different version of the impression when he did Dole on The Dana Carvey Show
03:17
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
25:46
Robert Smigel on why he left Late Night with Conan O'Brien, and on what made that show unique
06:05