There is a three episode story arc in Louie, Louis CK’s brilliant dark FX television series, where the titular character is purportedly up for a gig as the replacement for a retiring David Letterman. The elements in the arc are fantastic and surreal: David Lynch as a show fixer who seems to exist out of time and has an unpronounceable name; Louis’ supposed friends Jerry Seinfeld, Jay Leno, and Chris Rock all behaving in duplicitous fashion; the scheming network executive depicted by Garry Marshall; and all of it begun because Louis went viral on the Tonight Show where he was funny about airplanes.
Of course, the last bit was something Louis actually did, and he did it on Late Night With Conan O’Brien in 2008. This preceded the incredible story arc of Conan’s replacement and subsequent sabotage by Leno at NBC, itself a pathetic and underhanded display on the part of the network unaware that late night as a TV format was headed down the tubes.
It’s interesting to consider, though, that the Louis bit — which went viral at a time when that was something new and unique — never would’ve happened without Conan O’Brien getting a shot at doing his bizarre show in the first place. In retrospect, it’s stunning to think of the success the man’s career spawned and touched throughout the world of comedy for nearly thirty years.
O’Brien had just turned 30 when he was handed the opportunity to host Late Night, and the team of writers he assembled included Louis CK, Bob Odenkirk, Robert Smigel and more — absurdists who fed off a comedic energy which appealed to the young and puzzled the old. This lanky, pale, fidgety oddball who seemed simultaneously 13 and 130 — what was he doing in the grown man’s world of late night television? Well, it turned out he was inspiring a generation of comedians — the final sequence of his TBS show has churned through one tribute after another — through a dedication to crazy, wacky humor your dad didn’t get.
Right before O’Brien got the job at NBC, he had been working as a writer on The Simpsons, and famously penned one of the greatest episodes in the entire series: Marge vs. The Monorail, a Music Man parody that manages to be so much more. The absurdist nature of the episode was controversial at the time — Yeardley Smith, in keeping with her role as permanent buzzkill Lisa Simpson, pronounced it one of the worst episodes — but it represents the kind of timeless, ridiculous humor that O’Brien would personally bring to television as a host.
O’Brien gives no indication of having any political differences with the other hosts in his sphere – he’s interviewed the Obamas and Hillary Clinton on his podcast, and his sidekick Andy Richter is a notorious leftist troll online – but he never leaned into politics on his show. Perhaps if he had he would still have one, but that would’ve taken away from the form of comedy he represents, and it seems he understands that. He would rather make you laugh than make you clap.
Nowadays, O’Brien exists as part of that expanded universe of podcasts where people reminisce about Lorne Michaels. In his interviews, his penchant for dark humor remains vibrant in a way that seems completely out of touch with the self-serious hosts of today. On an episode of Conan O’Brien Needs A Friend from 2019 with Bob Newhart, there is a sequence around the 57th minute where the delivery is just perfection. It’s absolutely hilarious, and it also seems like the type of joke that would get you a call from the network. And that’s the kind of funny Conan O’Brien brought us. He will be missed.