Getting Introduced to Conan’s Dark Side in ‘Conan O’Brien Can’t Stop’

It’s no secret that sometimes comedy is taken a bit too seriously. Comedy obsessives love not just the jokes, but the mechanics and emotions of the comedy world. There are a raft of comedy documentaries exploring comedy and comedians, but do they really have anything significant to add to the discussion? This series looks at comedy documentaries and whether they’re interesting, insightful, and possibly even…funny?

There are few comedy documentaries as prominent as Conan O’Brien Can’t Stop. Then again, there are few comedy personalities as big as Conan O’Brien, and few comedy stories as notorious as his memorable departure from The Tonight Show in January of 2010, when comedy nerds and ordinary folk alike were fixated on the drama engulfing one of the most respected comedy institutions in the country.

The documentary follows O’Brien as he hits the road with his Legally Prohibited from Being Funny on Television Tour. The film’s focus is on O’Brien’s astonishing work ethic and drive; planning the next stage of his career began on the day of his last Tonight Show. “I don’t know what it would be like to stop,” he says early on. “What do you mean, stop? What does that even mean?”

But the real thesis of the film comes a bit later. “I might be a fucking genius and I might be the biggest dick ever. I don’t know. Or maybe both.” There is certainly ample evidence to support both sides. On the genius end, his boundless energy is incredible, and he’s genuinely funny even when he’s exhausted. Though the film can’t use any material from his NBC shows, “genius Conan” has been seen on TV for years.

But it’s his showmanship that also brings out his worst side. Even when he’s tired, cranky, and bitter, he can’t help but entertain the legions of well-wishers and friends who want to see him. How awful it must been have been for anyone he met on that tour to watch this documentary. In person, he seemed so happy to see everyone; in the film, he can’t stop talking about how much he hates it. It’s especially true of a staged birthday party, where he walks towards the room complaining about how it’s “exactly the opposite of what I would have wanted,” then exclaims, “This is great!” as he enters the party.

His nastiness is a result of a Hollywood-stroked ego. There are many times in the film when O’Brien wants sympathy for his brutal schedule, but it’s hard to feel too bad for anyone in a private jet, especially someone who, over the course of the documentary, compares himself to Mozart, Napoleon, and Anne Frank.

The film’s biggest strength is that it’s so intimate that the viewer becomes, in a sense, an expert in “Conanese.” When a wardrobe guy is showing him clothing options and says he can pick whatever he likes, he snaps in “on” Conan-style, “Don’t talk to me like I’m a child.” He then immediately downshifts. “Don’t put up with it, just stand up for yourself.” And, in that moment, I actually do feel sorry for him. He is a genius, and a dick, and he can’t stop being either one.

And so, in conclusion…

Is it interesting? Absolutely. It helps that the portrayal of O’Brien is far from reverential — it would be hard to blame anyone for disliking him by the end of the film. Some people seemed taken aback by the darker, crueler side of O’Brien revealed in the film, but it feels like a natural flip side to the goofy string-dancer of late night.

What does it have to say about comedy? Comedy, interestingly enough, isn’t a major focus. O’Brien’s writers are around a lot, but we don’t seem much of them actually writing. It gives the impression that being funny is the easy part for him; the rest of the job is the struggle.

Is it funny? There are some cute gags, both intentional ones like O’Brien pretending to receive a telegram from Jay Leno that finishes with the line, “What’s it like to have a soul?”; and unintentional jokes like him confidently telling his producers, “We’re not going to TBS.” But overall, the film isn’t too concerned with being comical.

Can I stream it on Netflix? Yes!

Any comedy documentaries you’d like to see discussed? Do let me know.

Elise Czajkowski is a freelance journalist in New York City. She naps frequently.