The film opens with a short segment explaining the events which transpired to culminate in O'Brien's launch of the Legally Prohibited Tour.

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.

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 (such as Jon Hamm, Jack McBrayer, Jack Black, Kyle Gass, Jon Stewart, Stephen Colbert, Jim Carrey and Eddie Vedder, the latter four appearing on the show) are shown — not all of which are pleasant for an increasingly exhausted O'Brien as the tour progresses.

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 (yet occasionally passive aggressive) banter till the close of the film.