Conan O'Brien Can't Stop (2011)

And so this is a tricky movie. It takes place just after O'Brien lost his job on "The Tonight Show." O'Brien began his career editing the Harvard Lampoon, and writing for "Saturday Night Live" and "The Simpsons." In 1993, he won the job replacing David Letterman on the "Late Night" show, where he resided until 2009.

In 2009, O'Brien officially took over "The Tonight Show" from Jay Leno and hosted it for seven months. Leno's new prime-time show began tanking and executives decided to juggle schedules so that Leno could come back to his old time slot; for the first time in its fifty-year history, "The Tonight Show" would be pushed to after midnight. O'Brien balked and chose to leave.

It's hard not to identify with O'Brien and his anger here, but this anger is on display throughout Conan O'Brien Can't Stop. He explains in one early scene that his frustration usually takes the form of ribbing; he picks on his friends, family, and underlings relentlessly. It's at this point that O'Brien decides to do a live performance, since he is barred by contract to appear on television, radio or Internet for six months.

He begins preparing for the show, which will have music as well as comedy. He also begins picking on his crew. Some of them, like his personal assistant, or his old sidekick Andy Richter, who goes along on the tour, seem to be able to shrug off the abuse. Others seem to take it personally.

As the tour goes on, O'Brien becomes more exhausted, and more unpleasant. He complains bitterly about having to talk to press and fans after shows, but he can't seem to help himself; he thrives on it. His jokes become increasingly arrogant and egotistical (whereas Richter remains hilariously funny throughout), and we begin to see a psychological pattern, one that perhaps O'Brien himself doesn't even recognize.

So the question remains: is O'Brien really like this? Was he under an intense amount of pressure here, both angry from his treatment at NBC and also keyed up over his tour? Either way, it's rather astonishing that O'Brien would allow this movie to see the light of day, and it's perhaps even more astonishing that anyone would allow this movie to see the light of day. How many movies about a comedian manage to get into his psyche, rather than concentrating on jokes? It's even more telling that the movie focuses more than half of its energy on O'Brien's music (mostly covers of blues-pop songs). It has been said that many comedians are merely frustrated rock stars, and O'Brien proves it.

I expected to laugh and to maybe find out a little more about the origin of O'Brien's silly hairdo, but instead I got a portrait of a psychologically needy, unhappy fellow. He may not be the most fun to hang around, but you won't find a more honest showbiz documentary anytime soon.

Magnolia released a very sharp Blu-Ray edition with a commentary track by O'Brien, Andy Richter, the director Rodman Flender, Mike Sweeney, and Sona Movsesian; oddly, they seem to be having a great time talking -- with Richter cracking the best jokes -- and no one notices the oddly negative portrayal of O'Brien in the film. There's a fairly generic interview with O'Brien, outtakes, and trailers.