Conan O'Brien keeps saying this goodbye is a good thing.
After 28 years as a late night talk show host, spanning three different shows on two networks, he leaves the nightly grind tonight. He'll sign off from his TBS show Conan, presumably for good.
But in watching a run of half-hour episodes leading up to tonight's finale, it seems there's something else going on underneath the smiles, nostalgia and good times.
Featuring a roster of longtime pals, the final episodes can't help feeling a little like a wake – if a fun and good-natured one. Seth Rogen let it slip that he was about 12 years old when he first watched O'Brien on TV back in the mid '90s; another sign of how influential the host has been for a generation of comics in ways that are rarely credited.
"This is the kind of thing you do when you know it's over for you," O'Brien joked during Rogen's visit, as he lit up a joint that the actor and cannabis entrepreneur brought with him.
Given that O'Brien will soon lose his status as late night's longest tenured current host, it was easy to read a double meaning in that moment.
TV's late night misfit
To me, despite his longevity, Conan O'Brien has always seemed like a host who never fit in easily on television – perhaps, at least in part, by design.
His history with Conan on TBS seems a poignant example. Created in 2010 as his landing spot after getting maneuvered out of hosting NBC's Tonight Show, the then-hour long show developed a robust online presence and filmed episodes in Cuba, Armenia and South Korea, evolving into his Conan Without Borders specials.
But it never developed Nielsen ratings to match what O'Brien could access on a broadcast network (The Wrap website reported this week Conan's ratings have declined 29 percent during the current TV season, averaging about 282,000 viewers a night). Instead, the show has leaned into creating online content for fans to consume on YouTube and through his website, mirroring how many viewers now seem to connect with talk show content.
Conan went on hiatus in 2018, coming back months later as a stripped-down half-hour show without a band. Now, O'Brien is leaving TBS altogether, with plans to debut a weekly variety show on corporate sibling HBO Max. He's also got loads of multimedia projects going under his Team Coco banner, including podcasts (Conan O'Brien Needs a Friend, Literally with Rob Lowe), stand-up specials from other comics, merchandising and more.
O'Brien told WHYY's Fresh Air back in 2019 that "what I don't want to do is sleepwalk my way through my career at this stage," hinting at a restless spirit which has powered many of his recent projects.
Still, this transition feels like an odd combination of O'Brien leaving late night TV as the genre leaves him. His smartly silly comedy — disconnected from politics, celebrity worship or anything resembling showbiz cool – is now beloved by a sliver of the TV audience too small to sustain a regular gig, even on standard cable.
Even as new voices like Amber Ruffin, Desus and Mero and Ziwe try to reinvent late night talk for a new generation, O'Brien is headed for the exit, seemingly eager to redefine himself before the industry does it for him.
Carving and sustaining a distinctive voice
I remember that O'Brien also didn't seem to quite fit in when first entered the late night talk arena way back in 1993, taking over NBC's Late Night show after David Letterman left for CBS.
Despite stints as a writer on both The Simpsons and Saturday Night Live, O'Brien seemed an untested talent back then who hadn't built his persona in public, like the former standup comics who hosted all the other late night talk shows.
It took years for his version of Late Night to gel, as the network initially hedged its bets by refusing to give him a long-term contract. Airing at 12:30 a.m., he was on the fringe of late night, speaking mostly to college students and insomniacs long before video clips on the Internet could spread awareness beyond those who watched it on NBC.
His version of Late Night eventually won over critics and the public, fueled by quirky bits like a guy in a bear suit who couldn't stop fondling himself dubbed the "Masturbating Bear." But when it came time for O'Brien to take over the venerated Tonight Show from Jay Leno many years later in 2009, the cutthroat politics of late night TV intervened.
Leno didn't actually leave NBC when O'Brien moved up. Instead, Leno got the network to give him a primetime show at 10 p.m. Ratings for both Leno and O'Brien cratered; months later, O'Brien was leaving NBC with a payout reportedly north of $30 million.
It's worth noting that, along with his own talents – including rapid-fire wit and fearlessness as a performer — O'Brien has had some outside help crafting his unique showbiz journey.
After Saturday Night Live empresario Lorne Michaels picked O'Brien to take over Late Night, I marveled at how much time NBC gave him to pull that show together. When O'Brien needed a place to land after leaving the Tonight Show, TBS convinced George Lopez to move his existing talk show back one hour to midnight and make room for Conan. (The midnight edition of Lopez Tonight would be canceled less than a year later, ending the journey for a pioneering Latino late night TV host).
I always wondered where late night TV diversity would be if hosts of color got similar support in the past.
These days, despite nearly three decades in the trenches of late night TV, it's tough to zero in on the legacy O'Brien will leave. In the end, it may just be the story of an irrepressible talent who always found a way to shine wherever he landed, fueled by his own quirky comedy sense and relentless drive, regardless of what was going on around him.