Director: Rodman Flender
Year Released: 2011
Good-natured egotist O'Brien, after getting bumped from his job hosting The Tonight Show - so the NBC executives could give it back to Jay Leno - decides to hit the road with his house band (and Andy Richter) to sing, tell jokes and revisit various skits from the show. The trouble is, the 'dramatic core' - O'Brien's 'disappointment' with being relieved of his duties - is muted in large part by the fact that he received a massive payoff (millions and millions) in his firing and that he genuinely seems unflappable: he throws a few sarcastic remarks at his crew and friends, but he's never mean-spirited, and always seems eager to meet-and-greet. A similar documentary about, say, the moody, insecure David Letterman might have had a little more tension going for it: this is a fan video about a witty man who takes the party with him ... on a private jet.