The film opens with a short segment explaining the events which transpired to culminate in O'Brien's launch of the Legally Prohibited Tour. It focuses on the rift with NBC and the outpouring of support shown by his fans while the fiasco played out. The documentary continues with O'Brien explaining that the idea for the tour came to them while thinking of things they could do in the six months after his exit from NBC, during which time he was legally prohibited from appearing on television, radio or the Internet. The following segments show glimpses of the thought process for the tour, and then an extremely nervous Conan and team members as they wait in realtime to see the results of whether or not their show would sell. All the venues begin to sell out at a fast pace and the stage is set for them to proceed with the planning of the tour. The rest of the documentary details the creative process behind various jokes/musical acts by O'Brien's team. In between segments of the live show, the film depicts Conan interacting with fans, attending functions, hosting an entire day at Bonnaroo and encounters with celebrities are shown — not all of which are pleasant for an increasingly exhausted O'Brien as the tour progresses. O'Brien worries that he will get burned out and be unable to return to television, leaving his team without jobs. He holds a secret show for his fans at the studio of Jack White, with White participating in the show itself. During the film there is little interviewing between Conan and director Rodman Flender, though the few questions that are captured are answered in great detail. A constant companion during the entire documentary is O'Brien's personal assistant, Sona Movsesian, with whom he shares humorous banter till the close of the film. The documentary ends with a title card displaying the end date of the tour and that Conan had a few weeks off before starting his next assignment as the host of his cable talk show at TBS, a shot of Conan walking out onto the studio stage after the Conan theme is played by the band is shown after the title card. A performance at Jack White's studio is played while the credits roll.
Reception
The documentary was given a limited release, and it was generally well-received by film critics. At movie review website Rotten Tomatoes, the film has received an aggregated score of 80% from 70 reviews. Film criticRoger Ebert gave the documentary three out of four stars, stating, "To be sure, NBC paid him $40 million in a send-off package, but the Conan O'Brien we see in the film wasn't in it for the money. He was in it because he can't stop." The New York Times review by Stephen Holden was critical of the film's subject and its direction which left much of the tour's performances off camera, stating, "The film spends too much time with Mr. O'Brien and his team backstage, where he is the needy focus of attention at all times." Holden did state though, that as a whole, the documentary is "consistently watchable".
