Conan O’Brien on Taking His Travel Show to Mumbai, Manila, and Beyond

When was a moment when things went the other way?

In Amsterdam, we had this idea that I would dress as Van Gogh and go to the Van Gogh Museum and walk around and look at the paintings, and loudly bemoan the fact that I never made any money in my lifetime. First, we showed up to the wrong museum. Then, we ran across a park—and I’m really running there when you see me—and I got to the Van Gogh Museum and the security guards wouldn’t let me in because it was closing. Then one of them took out a little book and was writing in it for no reason. I didn’t know what he was writing, and I started to say, “Oh, you—is this a diary entry? Dear diary? Van Gogh is here!” They really wanted me to go away then, and that made for a much better segment.

We didn’t anticipate any of that. In fact, we weren’t even sure we were going to do the Van Gogh bit because it was getting late in the shoot. We were tired. I thought: Do I really want to put on a beard, and a silly hat, and a silly costume, and make an ass of myself in front of a lot of people? But then something in me said, We have to do this. Let’s just go. And so we did it, and it’s my favorite thing in the Netherlands episode.

Is it a challenge to keep improvising while being chased by a security guard?

Oh well, you know what’s funny? I am at my happiest when things are a little off-kilter. 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. I’m a very hyperkinetic person. I’m happy when things are getting untethered.

There are moments, say at a fan’s family home in Casablanca, when a joke gets lost in translation. How do you make peace with the comedy not landing?

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. I have to remind myself that it’s not just me and this person who perhaps doesn’t know what I’m talking about. Take when I try to play cricket in the street in Mumbai. I’m wearing this stupid outfit and doing everything wrong, and this young kid is yelling at me because I don’t know the rules. Even though he doesn’t find me funny at all, there is comedy in that. I become this giant accident, this American idiot, if you will. Actually, that’s something I really like about the show: I never intended this, but Americans currently have a certain reputation that’s inescapable, and so I revel in a 16-year-old treating me with no respect, because I don’t deserve any. I guess what I’m saying is that I am an absurd person, and I’ve been an absurd person for many decades, and perhaps that’s my form of diplomacy.