From Harvard to Hilarity: Who Is Conan O’Brien?
Before Conan O’Brien became the gangly globetrotter we know him as today, he was a magna cum laude Harvard grad with a 160 IQ, a sharp pen, and an even sharper sense of the absurd. He cut his teeth in showbiz writing for ‘Saturday Night Live’ and ‘The Simpsons,’ where his arrival coincided with a pivot from grounded family satire to surreal brilliance.
In 1993, Lorne Michaels of ‘SNL’ handpicked O’Brien to take over NBC’s ‘Late Night’ after the retirement of David Letterman. The press balked, as the red-headed writer was generally unknown, too strange, and even too tall. But O’Brien turned his admittedly shaky start on ‘Late Night’ into a revolution for the genre. ‘Late Night with Conan O’Brien’ became a haven for absurd sketches, awkward humor, and delightfully worded pre-shot segments. Over Time, he’d come to helm ‘The Tonight Show,’ ‘Conan’ for TBS, and eventually redefine his persona with ‘Conan Without Borders.’ In 2024, he debuted ‘Conan O’Brien Must Go,’ an international travel series from his wildly successful podcast, ‘Conan O’Brien Needs a Friend.’
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You Must Go Watch ‘Conan O’Brien Must Go’
‘Conan O’Brien Must Go’ begins every episode with the iconic, accented voice of filmmaking legend Werner Herzog. In his incredible drawl, he brands Conan as “the defiler,” a perfect entrance to a Season 1 that not only brought Conan back to our screens but established the show’s rhythm: beautifully-shot country vistas serve as backdrops to Conan’s crashes into strangers’ lives. After meeting them on his podcast, ‘Conan O’Brien Needs a Friend,’ O’Brien flies out to a foreign country, enters their lives, and the chaos blooms from there.
The series opens in Norway, and Conan, of course, becomes a Viking, “Conan the Red.” In Argentina, he dies after faking a foul on a football field and is memorialized by a mural, flanked by a painted Messi and Pope Francis. In Thailand, he enters a bizarre singing contest after 30 minutes of practice, singing in Thai– he does not necessarily nail it, but he sure as hell owns it. In Ireland, he tries to lure U2’s Bono with a fake humanitarian award and discovers his true Irish culture.
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Season 1 of ‘Conan O’Brien Must Go’ is based in a surreal, global improv world, tossing Conan into increasingly bizarre and awkward scenarios with a sincerity that borders on the deranged. Conan brings his trademark charm to lessons on the culture, cuisine, and people of the country of choice. Season 2 picks up in the same way, this time in Spain. Conan fumbles his way through lessons on Spanish etiquette, opting to kiss everyone in the restaurant he is in goodbye on the cheek, as per his misunderstanding of the Spanish custom. He does dubbing work and attempts a loose investigation of masculinity with Javier Bardem as they traverse his home country. This all culminates in a visit to a museum featuring Goya’s ‘Black Paintings.’ His chemistry with guest Javier Bardem is thrillingly unscripted and magical. The comedy of ‘Conan O’Brien Must Go’ often comes from the fact that Conan is doing things he should not be doing abroad, forgoing landmarks and food tourism for genetic tests and rock climbing at a Thai gym. Season 2 of ‘Conan O’Brien Must Go’ promises more of the absurd travel planning.
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What sets this show apart from Conan’s other work is its ability to balance the absurd (Conan yelling in agony, fake blood pouring out of his mouth after he’s fouled at a fake Brazilian football match) with moments of unexpected humanity. Whenever he shows up at a fan’s home unannounced, despite the shtick, there is always real joy in connection. This is not traditional travel programming, but a high-production-value improv where the host does not just observe his subjects, he becomes them. With sketches, bizarre editing, and visual effects choices. And guest cameos (Jordan Schlansky’s horrifically catty dinner in Buenos Aires remains my favorite fever dream), Conan pushes the limits of how weird and genuine a celebrity travel show can be.
In an age of overly polished travel shows, Conan’s awkwardness remains a revolutionary force in the comedy world. He is not trying to serve viral moments, he is just trying to survive the chaos he creates. That is what makes the ride with Conan so fun, and why Season 2 might be better than the first.
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The Hair, the Wit, the Leadership: Why Conan Will Always Work
Despite going off the ‘Late Night’ air almost two decades ago, Conan is thriving. In an era of sanitized late-night sameness, his authenticity and weirdness continue to be his superpowers. As a host, he leads with a blend of emotional intelligence and total absurdity, a welcome mix of the wittiness of David Letterman with the insanity of Eric Andre. His charisma is rooted in his clear intellect and a lifelong commitment to not taking himself too seriously.
Off-camera, Conan is known for supporting his team financially and emotionally, especially after career lows like the ‘Tonight Show’ fallout. He is the rare breed of host whose loyalty to his crew mirrors his loyalty to his fans. His improvisational agility and willingness to appear foolish make him relatable, even when interviewing the President of the United States or filming in North Korea (somehow). His remote shows, whether in Finland, Cuba, or an Armenian market, are as much cultural exchanges and odes as they are comedy bits. The joke is never on the culture of the country at hand, it is on Conan’s slyness and offbeat quirks.
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Conan O’Brien is a brilliant traveling comedian because of his insistence that the joke be on himself. While he does poke fun at the fans he visits, or his guests on his talk show, it is his awkwardness, surreal level of confidence, and sharp wit that make him the main comedic focal point who victimizes no one. It is the mix of surreal humor and genuine curiosity that has made Conan the longest-serving host of the ‘Late Night’ run, and now, the 2025 recipient of the Mark Twain Prize for American Humor.
Conan Keeps Going: What is Next for the King of the Awkward
As is typical of Conan, his next chapter includes a little bit of everything. He will return to host the 2026 Academy Awards after his incredibly successful gig at the previous ceremony, firing shots at anyone in the audience and handling goofs and scandals with ease. He will take on a dramatic acting role in ‘If I Had Legs I’d Kick You,’ alongside Rose Byrne and A$AP Rocky. A dramatic turn from O’Brien promises to showcase another side of the versatile performer we have yet to see.
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Between his continued work with the Team Coco brand, future podcast seasons, and many more great guests, and likely more international escapades, Conan’s newest chapter looks to be his strangest and most delightful yet. For a man who once said he would walk around New York until an idea came to him, he is now charting a global path that few comedians could ever achieve.
New episodes of ‘Conan O’Brien Must Go’ premiere every Thursday at 9 pm PT on Max.
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