Conan O’Brien’s move away from the nightly talk show post he’s held down for 28 years continues an evolution seemingly born both of farsighted showbiz agility and, over the years, a David Letterman-esque desire to cut back on the standard showbiz element entirely. When Conan shifted from a full hour to half that airtime back in 2019, Conan himself downshifted into a gear that wasn’t so much slower as more driver-friendly. At the time, O’Brien spoke of remaking his TBS talk show into “something leaner, more agile, and more unpredictable.” In practice, the new, shorter Conan accomplished that goal by shedding much of the baggage and ballast he’d inherited upon choosing to jump into the already-built wheelhouse of a format he’d gradually—and gloriously—outgrow.
O’Brien’s growing pains as he attempted to cram his outsized comic talents into the late-night hosting network monkey suit are well documented at this point. Appearing at first like the overmatched new kid in network late-night’s established playground, Conan foundered as his Late Night With Conan O’Brien became best known initially for dead spots and anxious titters at this (to the TV public at large) neophyte nobody’s flailing efforts to ape the polished and professional chit-chatting stylings of genre mainstays like Johnny Carson and O’Brien’s own crankier but nimbler Late Night predecessor, David Letterman. It could be argued that O’Brien never did get good at the late-night fundamentals, as his initial reddened flustering gave way to a notable inability to make transitions into each guest’s requisite pre-cleared anecdotes sound conversational. Experience (and perhaps a touch of boredom) only made it more difficult for the aging O’Brien to feign interest in whatever WB series or debut pop album his third guest of the night was there to plug.
The shift came when Conan seemingly remembered that he was Conan-fucking-O’Brien, dammit, and, with the boldness of a guy who knows things can’t get any worse, started kicking against what he gratifyingly discovered with the self-imposed limits of just how much Conan O’Brien Late Night could encompass. This was the Conan who invented Springfield’s monorail, and Saturday Night Live’s Mr. Short-Term Memory, for crying out loud, and soon Late Night teemed with masturbating bears, the Walker, Texas Ranger lever, and the legendarily meme-spawning heavy metal guitar god and judge of social propriety, Clive Clemmons. (Played by longtime O’Brien abetter Brian Stack, just one of the myriad like-minded sidekicks, writers, and hilariously combative frenemies joining stalwart comedy partner Andy Richter at O’Brien’s side over the years.)
Conan, essentially, went Conan. And while his decision to take over a departing Jay Leno’s plum gig on The Tonight Show was an infamous disaster, honestly, it couldn’t have gone any other way without that earlier, much squarer late-night institution sapping away all of Conan’s Conan. As the Tonight Show faithful stared silently at any hint of O’Brien’s off-the-wall comic originality and sparking weirdness, the writing scrawled ever more bloody and ominous letters on the NBC wall until, as seems to be Conan’s most fruitful and natural state of mind, the straitjacketed host just said “fuck it” and went out with a weeks-long viking funeral of extravagantly silly budget expenditures and returning old school bits. (And one of the all-time classiest exit speeches in history.) The current, Jimmy Fallon-hosted incarnation shows just what it would have looked like if O’Brien had truly succumbed to his Tonight Show fate—a wan, charmless cruise of effortful wackiness and placid fawning.
So Conan moved to Conan and TBS, where he was freed up once more to be himself, albeit still chained to an interviewer’s desk by the dictates of the form. And for the show’s first near-decade, that’s where O’Brien stayed, plying his signature brand of agilely self-deprecating showbiz interlocution while letting his and his writers’ silliest premises play out, to our unending benefit and delight. Notably, the first things O’Brien ditched in his 2019 changeover to the half-hour format were the desk and the suit, opting to chat with his single, hand-picked guest each night from both an easy chair and some of his own casual duds. But those were just the cosmetic changes the self-admittedly restless (if not relentless) O’Brien was chafing to make.
When O’Brien took over Late Night, the late-night hosting post was a cultural sinecure, a comic throne from which to bestow laughs upon those guests granted an audience. But Conan is not a removed and beneficent bestower—he’s a once-in-a generation comic jester, whose true place is down in the comedy trenches, leaping at every opportunity to find the joke, no matter where he lands. Jumping metaphors a third time, Conan’s not the ringmaster, he’s the funniest clown in the center ring spotlight, who’s also secretly the brains of the whole outfit.
As the TV landscape shifted with the advent of streaming, Conan’s sharklike comedy instinct saw him rush to see what else there was for him to play with, his filmed forays into travelogue and the world of gaming videos garnering the once desk-bound host a broader (and younger) audience belied by the so-so ratings of Conan’s more traditional form. (And, sure, sometimes, that desk drove recklessly around a mall, but it was still a desk.) Podcasting provided another audience (plus revenue and awards streams, much to the dismay of some podcasting mainstays), while his chosen podcasting format only amplified O’Brien’s creaky old man shtick, portraying him as a guy who’d only chat with people he finds inherently interesting. (And added a new pair of stellar sidekicks in assistant-turned-foil Sona Movsesian and established comedy and podcasting fixture in his own right, Matt Gourley.)
With his upcoming move to whatever the hell he’s going to be doing on HBO Max—we know it will be weekly, in the variety show family, and most likely weird, but that’s about it—O’Brien is finally, after almost three decades, stepping wholly away from a hand-me-down entertainment format that never quite fit him properly, and that he never really needed. And, unlike Letterman’s more genuine retrenchment into prospector-bearded semi-obscurity (and the occasional comedy emeritus Netflix sit-down), there’s a genuine sense of freedom and joy at the prospect of Conan O’Brien deciding to stay in the game, on his own terms. With a cushy HBO deal supplementing his thriving and hand-tailored multimedia Team Coco comedy empire, the late-night-battle-hardened, 58-year-old Conan is striding into a free-form, subscriber-subsidized playroom where he can get back to letting his legendarily febrile comic imagination do whatever the hell it wants. After 28 years, it’s about time.