TBTS Reviews: Conan O’Brien Can’t Stop

There’s a scene in Rodman Flender’s documentary Conan O’Brien Can’t Stop wherein the ex-Tonight Show  and Late Night host is trying to concentrate on material for his recent live tour when he notices a solitary fan standing outside the building, two stories down, trying to get a glimpse in the window at the comic. O’Brien seems to try to ignore him as he works, but he just can’t. Eventually, he sends an assistant down to see what the man needs and signs an autograph to him.

While it’s a nice gesture, however, it seems to also be a symptom of O’Brien’s neurosis — he seems to feel an unwavering responsibility to accommodate his fans, at times to the fault that he nearly loathes it afterward. And while it’s nothing new to see a comedian with a darker side, O’Brien’s situation seems to be different: his constant willingness to perform for anyone and everyone seems to be the very thing which wears him down emotionally.

Credit O’Brien for giving documentarian Flender full access; the filmmaker certainly makes good use of it. It’s not a particularly glamorous look at O’Brien, and it must have taken some balls to put one’s self out there on film like that, especially when he didn’t particularly need to. While the film’s consistently funny — mostly because O’Brien himself is consistently funny, even when cutting someone down or delivering a barbed insult — it’s also filled with moments of domineering perfectionism. One moment sees O’Brien reminding his much put-upon assistant that she needs to call her mother to let her know she made it to her destination safely, then mocks her while she’s on the phone. It’s both very kind and very stinging — not the work of a bully, but a personality who’s natural comedic talents don’t always manifest in pleasant ways.

To be fair to O’Brien in these moments, however, the film does focus on a tremendously stressful time for the comic: the months following his Tonight Show ousting and his decision and process of hitting the road to do a multi-city live show. The stress of the situation, which seems palpable through the film, would lead one to believe O’Brien isn’t normally this hard on people, or himself, but the pressure cooker of mounting a concert tour night after night can easily devour the mind. And one facet not driven adequately home is that the reason O’Brien decided to do the tour in the first place was to keep his staff working and earning money during their downtime before O’Brien took his next job. One gets the feeling, when taking this into account, that O’Brien’s not always manic to this great of a degree, but that Flender is chronicling an incredibly difficult time on many levels for the comedian.

At the end of the day, O’Brien’s tragic flaw seems almost to be his devotion to the people around him, even when he’s driving them harder and harder. O’Brien’s differing levels of interaction with others really defines the film and offers a clearer portrait of his psyche. He’s bull-headed and difficult with his assistant, writers and tour manager, he’s open and warm with his fans, he’s a ball-buster with his colleagues and friends (one scene sees O’Brien telling 30 Rock’s Jack McBrayer, who is hanging out with Mad Men’s Jon Hamm, that the sight is like “seeing the Monopoly man walking a pig on a leash’), and he’s relentless on himself. Tonight and Late Night sidekick Andy Richter, quietly present in the periphery of many of the film’s scenes, offers a great and calming presence to the proceedings, gleefully oblivious and impervious to O’Brien’s bombs — offering evidence as to perhaps why they exist so organically as a great comedy team.

It’s no spoiler that the film ends with the ending of O’Brien’s tour and the decision to take his new job at cable network TBS, and the final scenes see a drained Conan wrapping things up with his staff. With Conan O’Brien Can’t Stop, Flender ultimately turns in an intriguing case study of a comic who takes his lot in life so seriously it can wreak havoc on those around him, but can’t find any other way to operate. It’s a fantastic look behind the curtain at O’Brien (even the rough-to-watch scenes testify to the performer’s natural talents) and when all is said and done, it’s impossible not to like O’Brien, even for his exposed faults. These faults seem to be rooted in a genuine need to please others, which is precisely why O’Brien can’t seem to stop — and why you’ll hope that while he goes a little easier on himself, he won’t stop.