Conan O’Brien Still Can’t Stop: The Longest Active Man in Late Night

When you think of longevity in comedy, you probably think of late night talk show hosts. Johnny Carson hosted The Tonight Show for 30 years. They basically had to pry Jay Leno off television. David Letterman earned icon status over 33 years of sharp, ironic comedy. All of those guys are gone now, either off the air or, in Carson’s case, passed one. There is one man left in the world of late night whose longevity is impressive, especially given how much he had to endure in order to maintain that longevity. That would be, of course, Conan O’Brien.

Conan O’Brien is a genius. This was clear before he even stepped in front of the camera as a talk show host. He wrote for The Simpsons, including two all-time great episodes, “Marge vs. the Monorail” and “Homer Goes to College.” This alone made him comedy royalty, but then he was the surprise choice to replace David Letterman as the host of Late Night, and suddenly he found himself as one of a handful of people being asked to carry a late night talk show on the strength of their personality and comedy chops.

Conan began the job in 1993, and frankly it took perseverance right from the get go. It’s well-covered territory that O’Brien’s early shows were a little rough, and that he was hanging on by a thread. He was on short-term contracts, never knowing if he was going to join the likes of Chevy Chase and Magic Johnson in talk show infamy, and he didn’t even have past public success to fall back on. Even those of us who recognize O’Brien as a comedic genius can acknowledge that his early work was shaky, but he quickly found his footing, and within a couple of years he turned Late Night into the best of all the late night shows. It was a breeding ground for smart, weird, absurd humor. Younger audiences flocked to Conan, who, in his own way, was to the ‘90s and ‘00s what Letterman was to the ‘80s.

O’Brien stayed on Late Night until 2009, when he was finally promoted to the host of The Tonight Show. He had toiled in the 12:35am slot for well over a decade, but he kept riding it out, kept waiting for Leno to finally move on so that he could have his chance on the hallowed grounds of The Tonight Show. He had already replaced Letterman, and this was (kind of) his chance to follow Carson, or at least to host the same show he made famous.

With Andy Richter back in tow, and a move from New York to Los Angeles, Conan made his Tonight Show debut on June 1, 2009. It was a real accomplishment for O’Brien and the devoted fan base he had cultivated at his prior show. He was finally on the big stage, and, well, it was kind of a disaster. It wasn’t O’Brien’s fault, though. Was his Tonight Show as good as his Late Night? No, but the assertion that it was a disappointment in execution is unfair. Conan remained as sharp and goofy as ever, but he did have another transition to make. There were audience issues, which weren’t helped by the fact Jay Leno refused to leave television, latching onto it like a lamprey, and got himself a show that aired before O’Brien’s in primetime, where it was an all-time ratings disaster. That didn’t help Conan’s audience, it didn’t give him the opportunity to work through the kinks in a (comparatively) pressure free environment. Since things didn’t take off right away, and since Leno was right there, happy to undercut Conan if it could benefit him, there was a plan to push Conan’s show to midnight to allow more time for Leno’s show. O’Brien told NBC to jump in the lake, refusing to push back his show for Leno’s benefit, and his Tonight Show run ended just seven months later, after a mere 146 episodes.

This could have put the kibosh on Conan’s career. One wouldn’t blame him for cutting his losses. It would have been a fine career, albeit with an ignominious ending. O’Brien, though, showed his tenacity once again, picked himself up, and started a brand new show on TBS. He would not allow himself to be stopped by the whims of the fickle television business. Conan got a show with his name on it, and got to create it sui generis on a network whose few attempts at late night talk shows had all been short-lived failures. He got to be himself, and he got to do the show he wanted to do. He still does. The audience is not as big, but it is devoted. Ever since The Tonight Show debacle, Conan’s fans have been a part of Team Coco. He’s left to his own devices, allowing him to do all sort of interesting things. His “Clueless Gamer” segments are fantastic, and he’s stretched the very idea of late night television with his trips abroad to places such as Cuba and North Korea.

Conan has been on TBS since 2010, and there is no sign of him stopping anytime soon. He’s only 53, which means he could have several years of hosting his show left in him. There is nobody waiting in the wings. It will never quite feel like Late Night, but it’s a good show, and it’s very much Conan’s show. His sensibilities are always on display, which is what got people so excited about him in the first place. He’s a cagey showbiz veteran who long ago grew completely comfortable in front of the camera.

O’Brien has been hosting late night shows for over 20 years now. He’s been on TV almost as long as The Simpsons, the show he used to write for that is also the pinnacle for television longevity in many ways. That’s impressive longevity as it is, but it’s how Conan got to this point that makes his longevity so admirable. He’s worked on three different shows, and two different networks. He had to deal with critics lambasting him during his early days as a talk show host. Through this, he kept going and proved he was here to stay. He had to deal with basically being ousted as the host of The Tonight Show, a job he had long wanted. Conan bounced back from this to put together a brand new show on new network. He regained his footing, and proved that he will be on TV for as long as he wants. By the time all is said and done, he could be a late night host for 30 years or more.

It’s a glamorous job, being a late night host, but that doesn’t shield him from the stresses and anxieties that are inherent to being a human being, especially considering how often his job has been on the line. He is admirable for his humor and his intelligence, but the most admirable thing about Conan is that he never gave up, and has persevered through the vagaries of showbiz to achieve impressive longevity. Between The Tonight Show and his TBS debut, when he was legally prohibited from appearing on TV per his settlement with NBC, O’Brien made a documentary called Conan O’Brien Can’t Stop. Here’s hoping that remains true, at least for a while longer.