Conan O’Brien Keeps It Old-School

His true gift lies in his combination of an entertainer’s desperate desire to be liked and an antagonistic streak.

It took Conan O’Brien less than 90 seconds to upend Hot Ones. The YouTube interview show’s gimmick is simple: Celebrities eat successively hotter chicken wings while the host, Sean Evans, asks them well-researched questions about their life and career. Most guests are happy to endure painful spice while answering never-before-asked questions. O’Brien, on the other hand, shamelessly infused his own zany sensibility into the show’s design by immediately introducing “Dr. Arroyo,” his personal doctor and a man of dubious skill, credibility, and education. At one point, the character, played by O’Brien’s longtime writer José Arroyo, monitored his health by choking him to locate his pulse.

By the episode’s end, O’Brien had broken the mold of the show entirely. Whereas guests typically approach the final stages with caution, O’Brien recklessly poured extra hot sauce onto the already heavily coated wings, before drinking it straight from the bottle. When asked to promote his new show into camera, he resembled a Dionysian jester, his tear- and snot-stained face turned a deeper shade of red as a stream of milk dribbled from his open mouth. “You have to commit to the bit,” Evans told him at one point, impressed by his diligence. “It’s not a bit!” O’Brien exclaimed in response. “This is life!”

At the same time, O’Brien gamely answered all of Evans’s questions. He offered casual insights from years of hosting late-night television; he told an amusing, harrowing tale of a water buffalo wreaking havoc during rehearsal after he’d foolishly tried to ride it. He explained his modus operandi while proudly exhibiting it at every turn. This was standard for how O’Brien has carried himself, across his career: He respects rituals and conventions, but finds a way to mold them in his image. The instantly viral Hot Ones appearance, and the new travel show Conan O’Brien Must Go, reveal a somewhat obvious yet still remarkable truth about a man who’s been in the public eye for three decades: O’Brien is one of our last classic entertainers, and he represents a connection to an era of showbiz that has long since evaporated. His unique cross-generational appeal befits his particular arc, largely because his fingerprints have been left on so many touchstones—his omnipresence ensures that groups of 20-somethings have been “discovering” O’Brien since 1993.

I say “discovering” because, despite his name recognition, that is still how it feels to tap into O’Brien’s comedic wavelength. Born roughly between the Boomers and Generation X, O’Brien helped bridge the gap between old-school comedy and its speedy postmodern deconstruction. He got his big break writing for a long-running comedy series (Saturday Night Live), helped define the voice of another (The Simpsons), and led a late-night show for 28 years. He lived in the shadow of David Letterman, who defined doing the thing while making fun of it in the late-night space, but the key difference between the two was that Letterman developed his persona in front of the camera, while O’Brien built his among other writers long before he was ever given his own show. Late-night television, as pioneered by hosts such as Johnny Carson and Steve Allen, was designed to comfort, to provide a cozy hearth where guests and viewers alike could feel at ease. Though O’Brien always wanted his guests to feel welcome, his style was possessed with a comedy writer’s exacting, imaginative silliness, which helped enliven the conservative format into something distinct and fresh.

Much as he did with his Hot Ones appearance, he’s built a reputation on shaping established institutions in his own worldview, which allows him to move across broadcast and cable television, between various time slots and format changes, and, with his now-popular podcast, into different entertainment mediums. Many hosts feel most comfortable onstage in front of a studio audience, because of the arena’s inherent guardrails and clear power dynamics. But O’Brien frequently comes alive outside the studio, demonstrating a particular skill at worming his way into any environment and mining comedy from within.

Conan O’Brien Must Go, his latest travel special, serves as a prime example. The show’s premise is that O’Brien travels to his fans’ home countries and spends time with them on their turf, but it’s really an excuse to film improvised interactions. He records a song with a Norwegian rap duo, visits the Damnoen Saduak Floating Market in Thailand, and takes a tango lesson in Argentina, among other experiential excursions. It’s the best-looking, most expensive series he’s ever made, but O’Brien’s make-them-laugh-at-all-costs approach remains the same.

[Read: What Conan O’Brien means to late-night’s future]

As with all sketch comedy, the results are hit-or-miss. Sometimes O’Brien finds a groove in a certain setting, such as when he’s asked to appear in an Irish soap opera; other scenes drag because the core joke can’t sustain itself, like when he uses a gigantic pair of fake legs to take on multiple Muay Thai boxers at the same time. Nevertheless, the show’s familiar, flexible structure allows him to showcase his well-crafted on-air persona, and his easy chemistry with everyone, including members of his staff—whom he frequently puts on camera—and complete strangers. And whenever O’Brien engages with someone who implicitly understands how to play off this affable, somewhat arrogant goofball—like a local Norwegian man who calmly insists that O’Brien’s traditional Norwegian outfit looks ridiculous—the show comes alive.

In many ways, O’Brien’s true gift lies in his combination of an entertainer’s desperate desire to be liked and an antagonistic streak. Amid the outpouring of praise he receives for being such a nice guy, it’s easy to forget how much O’Brien enjoys acting like a jovial bully. Like a more juvenile, hammier Don Rickles, he can mock people to their face and embrace them at the same time—on the new show, he tells a small Argentinian child that his affect resembles Ted Bundy’s. O’Brien’s ability to make strangers feel comfortable being the butt of the joke comes from his eagerness to mock himself; he immediately conveys to the public that there’s camaraderie in becoming a punch line.  

“You can’t stop me from being who I am,” O’Brien tells Evans on Hot Ones, after the latter tries to warn him against liberally licking hot sauce off his fingers. This casual declaration might be the real reason for O’Brien’s cockroachlike longevity in an unforgiving, ever-changing industry. Like many others, I remember staying up too late to watch O’Brien’s Late Night show and wondering how he was able to pull off such flights of inspired fancy; it always seemed as though he was getting away with something. More than 30 years into his career, it still feels like he’s pulling off a trick behind somebody else’s back. Maybe that’s because, to paraphrase the man himself, it’s not a bit. It’s just his life.