A Farewell to TV for Conan O’Brien

Explaining a joke rarely supports how funny it is. Comedy as an art form tends to be self-explanatory. It’s either funny or it isn’t. Thus, writing about comedy can often feel like an exercise in futility when most can summarize it with a simple “it made me laugh.” Truly, a comedic talent has to be distinct, influential, and everlasting to be worthy of waxing poetic about. Luckily, the work of Conan O’Brien fits that bill to a tee. This week, Conan ends his eponymous third talk show on TBS and will not return to late-night television. While O’Brien does plan on crafting a new variety show for HBO Max in the near future, the hole he’s leaving behind in the talk show space is massive. Conan O’Brien has been on television for about as long as I’ve been alive. O’Brien became the longest-running talk show host because he always stood out from the norms of his competition. Even as the popular format for such programs morphed from the typical stodgy sit-down conversations to the modern blend of Nickelodeon game show and celebrity branding exercise it has now become. Conan’s specific brand of talk show stayed true to his spirit while constantly evolving.

When Late Night With Conan O’Brien first premiered on September 13, 1993, his current reign didn’t seem at all likely. In 1992, Johnny Carson announced his retirement, leaving The Tonight Show hostless. Everyone anticipated that then-current Late Night host David Letterman would fill the seat, including Letterman himself. However, NBC infamously decided to pick up-and-coming comedian Jay Leno to host the show, prompting Letterman to move to CBS and start The Late Show. At the time, David Letterman was the beloved weirdo chaser to Carson’s showbiz staple vibe. His sensibilities were a favorite among anarchist 20-somethings throughout the 80s. His move to CBS was the end result of an infamous public fallout that felt so much more dramatic than one would expect a talk show host transition to be. So, NBC hiring a fresh-faced and gangly 30-year-old comedy writer whose biggest credits up to that point were running the Harvard Lampoon in his college days and writing on Saturday Night Live and The Simpsons wasn’t a choice audiences were immediately receptive to.

Watching clips from the early years of O’Brien’s talk show career, you can see the host having clear self-doubts. His spindly frame and nervous laughter denote a kid who has no idea how he got this job, always looking over his shoulder in case 30 Rockefeller Plaza security was about to throw him out due to low ratings. These rough few years at the start built a thick skin for Conan, allowing his true comedic persona to grow. There’s an infectious charm that feels incredibly endearing from Conan as he evolved over his first few years. O’Brien gives off the energy of a giddy boy surprised that he got this position, constantly testing the waters to see how much craziness he can get away with before the network brass pulls the plug on him.

That giddiness allowed Conan and his collaborators to make things their own confidently. The back and forth between Conan and his longtime sidekick Andy Richter built this special rapport you didn’t find with Johnny Carson and Ed MacMahon or the various other host-to-sidekick dynamics on late-night TV. Given Conan always positioned himself as the outsider, Andy felt on par with him instead of at a lower tier. Their chemistry was built on being united underdogs, with Conan having the dorkier disposition of trying to prove himself as a host that bounced off Andy’s dry frank delivery. This even translated to the guests, who felt like they were being invited to a silly club of misfits rather than promoting a project. Conan’s energy even allowed for up-and-coming talents to blossom in bit parts like Amy Poehler, Jack McBrayer or JB Smoove. Conan’s inviting communal energy translated into a bizarre universe where anything could happen and any cartoonish characters could manifest. Characters like the Masturbating Bear, The FedEx Pope, and most infamously Triumph the Insult Comic Dog could only exist because of the insane stream of consciousness style that Conan O’Brien offered. 

All of these wacky trappings helped to turn Conan O’Brien into the unique voice of Late Night. O’Brien evolved from the nervous boy of a talk show host to becoming the surprisingly confident man who knew he was funny. Conan could poke fun at whatever targets were popular at the time but never forgot to ground himself with a fair amount of jabs. His humor managed to be self-deprecating yet never come off as self-loathing. O’Brien would constantly make jokes about his gangly features or nerdy personality but did so because it was the perfect joke for that situation. Even when the flimsiest premises of a skit would literally fall apart right in front of him, Conan embraced the moment with uncontrollable laughter at the perishing prop and idiotic conceit to thunderous applause from the crowd. A perfect example of Conan’s specific comedic voice is his field piece at Old Bethpage Village Restoration, a historical recreation group known for playing baseball with authentic rules and outfits of the mid-1800s. Conan’s ability to sardonically tear down those trying their best to stay in character while also embracing his love of archaic culture created a balance between a comedian and his humorous subjects. Conan was capable of having one foot in the shoes of the sardonic comedian while having another in the ecstatic excitement of a dork with no shame about what he loves.

This self-awareness allowed Conan to roll with many punches that came over the course of his career. Punches he always faced by being able to work a dead-end into a new creative opportunity. When his long-time sidekick Andy Richter left the Late Night incarnation of the show, O’Brien built a better rapport with recurring guests like Will Ferrell or Lisa Kudrow and gave staff members like writer Brian Stack or bandleader Max Weinberg the spotlight to craft memorable personas. When the Writer’s Guild of America Strike left him without direction in 2007, he made spinning his wedding ring on a desk an event and helped craft a massive crossover fake feud with The Daily Show’s Jon Stewart and The Colbert Report’s Stephen Colbert. While working through the embittering experience of losing The Tonight Show, he went on a comedy tour through North America and produced the revealing documentary Conan O’Brien Can’t Stop. Even during the Covid-19 pandemic that made live audiences impossible, O’Brien transformed the Conan show into a more chilled out intimate affair at the Largo Theater with only a couple of staff members and several cardboard cutouts in the audience.

Conan O’Brien isn’t someone who makes a decision like stopping a creative track lightly. He loves to explore every possible nook and cranny of a project he takes on until he rings every creative juice out of it. So, him ending his talk show career doesn’t feel like a sign of defeat as much as a desire to move forward. Given he’s been doing this for nearly three decades, it’s no wonder why Conan would want to move away from this familiar format and craft a show with more creative flexibility on HBO Max. Even as he was doing the TBS incarnation of his show, Conan experimented by doing travelogues to other countries or filming more brazenly weird skits and interviews to massive nerd crowds at San Diego Comic-Con. O’Brien has a clear desire to move on from the structure he’s been attached to for about 30 years and him breaking out of this creative constraint is just another octave in his ever-evolving comedic voice.

Still, seeing Conan O’Brien leave TV feels like the true end of an era. As other talk shows have devolved into desperate excuses to keep up with modern internet culture, O’Brien fit a comfortable space as a true original that never rested on his laurels. Conan evolved his comedic voice to appease audiences with integrity and honesty, not through a cynical desperation to follow what was popular. Conan O’Brien’s main desire was always to make the best show possible and to do so with the help of comedians, musicians, and writers he respected the talents of. I’m happy he’s moving forward into brave new territory, but part of me will always miss his specific place on television. It was a joy to see him get away with devoting time to horny manatees, Paul Rudd trolling people with a clip from Mac And Me, or pulling a lever to play random clips from Walker Texas Ranger. Truly, as only Conan O’Brien could do.