Conan O’Brien’s Unconventional Travel Show

The Emmy award-winning series, ‘Conan O’Brien Must Go,’ follows the comedian and podcast host around the world as he meets up with his fans in a diverse array of destinations, visiting their places of work and family homes while providing lively glimpses of everyday life.

Source: media.cntraveler.com

On paper, it might sound like your regular celebrity travel show, yet a blend of surreal improvisational comedy and appreciation of the absurd in the context of travel makes it something a little more unusual—particularly in the way in which he gives himself up to the unpredictability of cross-cultural exchanges and revels in its discomfort.

Source: media.cntraveler.com

“My goal is that you might not really learn anything about the country, but you do get a sense of the people,” says O’Brien. “I am basically there to be mocked.”

Source: media.cntraveler.com

From Sigmund Freud to Van Gogh

In past episodes, this has meant dressing up as Sigmund Freud in Vienna, singing with The Irish Tenors in Dublin, and facing off with a python in Bangkok. This season takes him to Morocco, India, the Netherlands, and the Philippines, where he continues to embrace the chaos of the unknown before “coming back with a lot of adrenaline and a slightly different perspective on what’s going on.”

So, what exactly has he learned from taking on the role of transcontinental clown? I spoke with O’Brien recently over Zoom to find out how he chooses the “fish out of water” situations he places himself in, connects with confused strangers, and what his own narrative arc as a traveler—which began early on—has crystallized for him about life when he returns home.

“I work with a great camera crew. We have terrific producers. A lot of thought goes into each episode, but so much of what ends up happening is very guerrilla-style,” O’Brien explains.

“I love trying to make something happen: If I just met you on the street and we started talking, I would probably try to make something fun happen in the moment. And those moments often yield good results,” he says.

There are moments, say at a fan’s family home in Casablanca, when a joke gets lost in translation. “I always remember that there’s another audience, which is the camera, so that when I fail, I can turn to them and look slightly deflated, and they might understand, even enjoy, seeing things not necessarily going my way,” O’Brien says.

In Amsterdam, he dressed up as Van Gogh and went to the Van Gogh Museum, but the security guards wouldn’t let him in because it was closing. Instead, he found himself running across a park, with one of the guards writing in a little book for no reason. O’Brien turned to the camera and started to say, “Oh, you—is this a diary entry? Dear diary? Van Gogh is here!”

The segment turned out to be his favorite thing in the Netherlands episode.

“I am at my happiest when things are a little off-kilter,” O’Brien admits. “I don’t know why, but in all the years that I was doing my late-night show, I was at my calmest when things got chaotic.”

Lessons Learned from a Life of Improvisation

So, what has O’Brien learned from his years of doing comedy in front of an audience every night? “The greatest thing in the world is an accident,” he says.

“If David Bowie’s on the show, and something goes wrong—perhaps his coffee mug breaks accidentally because it was cracked—that’s not a disaster. That’s the greatest thing that could happen because suddenly, something real is happening with this icon, and their humanity is revealed,” O’Brien explains.

When traveling, things don’t always go to plan. “They just don’t,” he says. “And so, if you are ready to find the humor in it, and improvise, and figure out another way, you’re going to have a great trip.”

“Making this show is a combination of preparing for something—and then preparing for things to go another way completely,” O’Brien says.

For O’Brien, the key to success lies in embracing the unknown and being willing to make a fool of himself. “I am never showing up to shoot comedy at strangers,” he says. “I’m there to try and get a spark going between us and see what happens.”

Why India Was a Highlight

India was a highlight of the season for O’Brien, who got to play cricket and sing and dance with fans in the country.

“I had been briefly once before, to shoot an American Express ad in Jaipur, and I’d always wanted to go back,” he says.

“It just felt like the most different place I could go and still be on Earth, in terms of the visual tapestries you see, the density and the chaos and the colors,” O’Brien explains.

He also got to visit the family home of a fan in Casablanca, where he tried to make a joke but it got lost in translation.

“I always remember that there’s another audience, which is the camera, so that when I fail, I can turn to them and look slightly deflated, and they might understand, even enjoy, seeing things not necessarily going my way,” O’Brien says.

He admits that he loves trying to make something happen, and those moments often yield good results.