Conan O’Brien Still ‘Can’t Stop,’ But Who’ll Keep Him From Burning Out?

Our favorite movies and music we can go back to whenever we want to find comfort, solace or escape. Comedians do that for us, too, in the here and now – although comedy, unlike other performing arts, doesn’t always hold up the same over time. Some jokes reference fleeting fads that make little sense decades later. Some work once or twice but lose their impact upon repeated listening. Some pushed envelopes then, but don’t seem so edgy or revolutionary now that everyone else does it; while others feel outdated or behind the times of current society. With that in mind, we bring you Humor in Hindsight, an ongoing column devoted to stand-up specials and comedy documentaries streaming online that, much like wine or cheese, give us more texture and better perspective with age.

Seven years after Conan O’Brien found himself stuck in the middle of bad buzz thanks to his TV network executives, it’s not quite déjà vu all over again, but TBS brass must be kicking themselves for how their negotiations with Conan over the future of Conan became public fodder for widespread media rumors and ruminations Thursday.

O’Brien and his faithful Team Coco employees and fans certainly wondered, joking obliquely in public and sharing their worries and frustrations with me privately.

All of which gives us reason enough to revisit Conan O’Brien Can’t Stop, the documentary that premiered at SXSW in 2011 and is currently available for streaming on Hulu, and Amazon Prime (via Starz). Directed by O’Brien’s old Harvard Lampoon pal Rodman Flender, the film opens on O’Brien in his car with the late-night TV host driving around Los Angeles in his newfound employment, shouting his name and credentials at a Hollywood tourist van as he passed.

“I should have said formerly of The Tonight Show,” he says, chuckling.

O’Brien replaced Jay Leno as Tonight Show host in June 2009 only to be discarded seven months later in what can only be described as an epic fail on NBC’s behalf. The Peacock Network had promised O’Brien the promotion from Late Night to Tonight in a highly-publicized peaceful transition five years earlier, only to first panic about losing Leno, then panicking again when an experimental (yet ahead of its time, both literally and figuratively) nightly primetime variety showcase with Leno tanked ratings-wise, and hoping O’Brien wouldn’t notice getting shoved back past midnight. If only they’d had the foresight to see how well Leno’s games and gimmicks would go viral with Fallon and his team at the helm.

Instead, O’Brien balked and NBC let him walk in January 2010 with a big payout that came with a six-month no-compete clause keeping him off TV, radio and streaming airwaves. What would he do? That answer found a quick answer as well as a narrative in Conan O’Brien Can’t Stop.

We know it’s 2010 because the film establishes the set-up via one of those Taiwanese animated re-enactments that were all the rage then.

We know now that the I’m With Coco fan movement begat Team Coco and teamcoco.com, and though they didn’t save his broadcast network gig, they did help lead him to his current role with TBS. In between, O’Brien realized he really could not stop, and would not stop, trying to find an audience, even planning his next public moves while his staff planned his final Tonight Show taping.

“What if I could just go out there and see these people, who were so nice and supportive, and put on a show for them?” O’Brien tells Flender. That show became The Legally Prohibited From Being Funny On Television Tour. “I just know that I’ve always liked being in front of an audience. That’s all I know.”

And when he doesn’t have a captive audience watching him onstage, he needs to perform or talk about performing with friends and colleagues. “I really have fun when I’m with writers or I’m with musicians and we’re working things out, then I’m content.”

The documentary captures everything magical we’d later see time and time again via Conan’s remote segments out and about Burbank and Los Angeles, and even more in his hourlong specials broadcast from foreign lands — with the added bonus of pulling back the curtain on the real O’Brien you don’t see four nights a week on your screens. O’Brien gets annoyed, mad, frustrated, sarcastic, physical, and sometimes all at once in production meetings. He’ll throw insults, objects and jabs at his staffers.

In a lighter wry moment, O’Brien’s longtime producer Jeff Ross (no relation to the Roastmaster General) goes over O’Brien’s meetings with his TV suitors in 2010. “Yeah, we’re not going on TBS,” O’Brien snaps, before adding: “When is our meeting at Oxygen, Jeff?” Off-camera, he then jokingly adds another tag; his ultimate destination? Animal Planet.

Later during the tour, O’Brien acknowledges to Flender that his comments with colleagues aren’t always really jokes. “I’m extremely hard on myself. Sometimes that spills onto other people.”

He’s more openly desperate to an audience, telling his former employees who attended his tour’s first dress rehearsal: “I’m like Tinkerbell. Without applause, I die.”

Both carry the same sentiment.

O’Brien has a compulsion to perform, to entertain. He needs to be on that stage, and he wants you to need him on that stage. Everything else? He might want to just chuck by the wayside. Although until he can do that, he’ll abide by his favorite improv rule: “Act as if this is completely normal.”

His 2010 tour production based an opening segment on the stages of grief, but the show itself was more catharsis than pure entertainment, both for him and his fans.

We briefly glimpse Reggie Watts — the tour’s opening act, who afterward became first a sidekick to a satirical version of a talk-show (IFC’s Comedy Bang! Bang!) and then a real late-night bandleader for James Corden on CBS. We also see plenty of other people, from 60 Minutes to industry types to other stars to actual friends to friends of friends of someone connected with the tour, all asking O’Brien for his time and attention before and after tour stops.

Some of it is sheer joy (see: Jack McBrayer and Jon Hamm in L.A., Eddie Vedder in Seattle, Stephen Colbert and Jon Stewart in NYC). Some of it is torture. Such was a WME agency pre-show party for O’Brien in Los Angeles, or a day-off volunteer performance as part of O’Brien’s 25th reunion at Harvard. Another day “off” for O’Brien managed to schedule a secret show for him with Jack White and fans at White’s Third Man Records studio in Nashville.

O’Brien wears his weary through profanity-laced venting on his most loyal assistants, but never loses sight of the impact of his zingers on them. “I might be a fucking genius, and I might be the biggest dick ever. I don’t know. Or maybe both! That’s what Patton was. Napoleon,” he says.

And he’s always careful throughout to accommodate as many fans as possible. And even when he’s griping about too many responsibilities at Bonnaroo, he’s still going to get back out there to entertain the 40,000 fans on the mainstage.

“I definitely got signed up for too much,” he tells his assistant backstage first, lying down on a sofa and clearly exhausted. “And moving forward, there’s a lot of not — no one’s thinking about burning me out. Nobody’s thinking about it. When I burn out, and everyone can’t get, doesn’t have a job anymore, they’re going to be pissed.”

TBS may have kept that in mind by going so public Thursday, even if they sent conflicting messages about how they’d keep O’Brien happy moving forward from 2017.

So they should also go back and watch how O’Brien let his anger show in 2010, playing a TV suit. “It definitely is me saying, to the whole idea of non-creative people screwing over people that feed their bone marrow into the wood chipper of television, ‘Fuck you!’ you know. That’s part of it.”

Let’s hope O’Brien keeps his bone marrow intact for as long as possible.

Watch 'Conan O'Brien Can't Stop' on Hulu