Conan O’Brien Photo: Dimitrios Kambouris/Getty Images

Late-night TV is a numbers game. It’s not about specific moments as much as an overall impression. No one knows that better than Conan O’Brien, who has been a late-night host for over two decades. So, how does he stay relevant in a crowded field as he approaches his 22nd year? Cuba! Tonight, O’Brien will air a special episode of his show that will put him as the first late-night host to be there in 50 years. Earlier this week, O’Brien spoke with John Horn, host of Southern California Public Radio’s new arts and entertainment show “The Frame,” about the special, doing comedy in a foreign country, and the ever-changing late-night terrain. (Listen to part of Horn and O’Brien’s interview here, and subscribe to “The Frame” at iTunes or Stitcher.)

Conan, welcome back from Cuba.

Thank you very much, it’s good to be back.

So just in terms of the landscape, when Letterman retires later this year, you will be the late-night show host with the longest run at nearly 22 years. So how much was this trip part of a way to find new things to do with the form and with your show?

Well, it’s huge. At this point, when you’ve been doing it as long as I’ve been doing it, the primary objective is to challenge yourself and to find ways to surprise yourself a little bit — see if there’s something you can do with the form that you haven’t done before. You’re just competing with yourself. I’ve always felt that way, I’ve always felt like I want to push it, I want to push the envelope, I want to try things, and that gets harder to do when you’re around longer. So, yes, the minute we realized maybe we could get into Cuba and be the first late-night talk show to be there in 50 years, it was thrilling.

When you first floated this idea to the bosses at TBS, what did they say? Or did you actually tell them you were going to Hawaii?

We didn’t actually tell them. We kept it on the down low, and then we told one guy pretty much that we were thinking of doing it, and he said, “That sounds cool.” We decided if we told too many people, either (a) it’ll get out or (b) someone will give us a really good reason why we can’t, or a legal reason why we can’t. We decided better to beg forgiveness than ask permission.

Do you think you could’ve pulled this off with a network like NBC, or are they too risk-averse? Is that the advantage of working at someplace like TBS?

It’s a good question. There are certainly advantages to being on Turner because they let us do pretty much anything we want to do. I like to think we show common sense, but they’ve been terrific partners. We may have been able to do it at NBC, but certainly it would’ve been a little trickier in terms of keeping it secret, ‘cause it’s a much bigger bureaucracy.

Obviously, relations between the United States and Cuba are changing. That opens the door, but as a comedy show, what did you think the potential [was] for content and comedy and creating something that was not just in Cuba but actually about something? What was that conversation?

It was important to me that there be no snarkiness. One of the advantages of my comedy fitting in a situation like this is that I like to make fun of myself a lot, especially in remote segments. I like the joke to be on me. I wanted it to be really funny and have belly laughs in it, but I also wanted it to be sweet. We very much went in with a feeling of, we’re going into another culture and we want to respect that culture, and all I want to do was try and make people laugh. I didn’t want to do comedy where I’m making fun of something in their society; that’s just rude. I wanted to go in as a good ambassador, but also to see if I could get them to laugh at my idiocy. Maybe that’s the common language that we all speak is that, whatever our differences, most people find me ridiculous.

What played and what didn’t play?

The key to something like this is just going with it; you can’t be in control. I got there and I wandered around with the camera crew. I don’t know if the government was aware that we were there, but nobody stopped us from doing anything. What really played was being a very physical comedian. That’s a universal language. Whenever I’m trying to dance or I’m trying to sing or I’m trying to speak Spanish to them, they’re laughing already. And I tried to dive into their culture. I tried to make Cuban cigars at an authentic Cuban cigar factory where they hand-make them, and I got the help of these different women and that ends disastrously, but they’re laughing. And I go to a rum museum, and that goes disastrously because I’m an Irish guy who really shouldn’t be drinking that much rum at 11 o’clock in the morning. But they’re all laughing at me, so that is the value of what we were doing. And we saw so much. We were there for four days, and I think I met about 150 different people.

How did you introduce yourself and the show to people? Did they have any familiarity with who you were, what the show was about? Do they have an equivalent late-night TV program?

The people who knew me were tourists from other parts of the world. As far as Cubans, they didn’t know, but there’s a segment where I walk along the oceanfront, the Malecón, and I’m showing young people my show on a tablet. And of course it’s just clips of me acting like an ass. I get a great variety of reactions, from them laughing and saying, “Sure that could be good,” to just staring at it and thinking, okay, do we really want to be involved with this country? The best I could do was just tell them I’m a comedy star. I actually did tell a number of them I’m the biggest star in America.

And they believe that ‘cause they don’t know better.

Exactly. But who’s to say I’m not.

That’s true. And what surprised you the most about the country?

When you grow up in our culture and in most of the capitalist countries around the world, you forget how much advertising you see everywhere. I mean, we’re just so inundated by advertising, we don’t even notice it. When you go to Havana, you notice something is very different right away and you don’ t know what it is. It took me a while to realize there are no advertisements. Occasionally you might see some propaganda.

So stepping back a little bit, you took this trip at a time when there’s amazing amounts of changes in late night. Letterman’s retiring, John Stewart announced he’s leaving The Daily Show, Colbert is on hiatus, what goes through your mind as a host when you’re in the middle of that much change?

It’s funny, but it’s always about running your own race. To the outside world, whenever they think about late night, they envision us all looking at each other’s shows and trying to outwit each other. But for me — and I don’t know what the other guys do — but for me nothing could be further from the truth. I just try to challenge myself and make myself happy and try to do a good show on my terms every day. I’ve been in this since 1993, and it’s constantly been in flux. Now is a particularly chaotic time, but I’ve seen this happen like five different times, you know? When I came on the air, Arsenio was on the air and Chevy Chase was on the air, shows have come, shows have gone, and my philosophy has always been, just keep my freak flag flying, just do my Conan thing, whatever the hell that is, the best that I can possibly do it. Everybody’s carved out their own niche at this point. It used to be that big Letterman-Leno feud for about five years, and people acted like it was Ali and Foreman going at each other, and you don’t get that sense anymore because everyone’s show is so different. In the modern era, people have realized there are 750,000 little pods of entertainment, and I can get them all 15 different ways, so it’s very hard to create that this-person-versus-that-person environment.

Other than recommending he apply to be an intern on your show, any advice for Jon Stewart?

Wow, I think he’s figured it out. I went on his show, and his whole thing is, “I want to get out while I’m on top,” and I said, “What if farmers had that attitude?” [Laughs.] What if farmers said, “Hey, you know, I had a really good crop so I’m shutting it down now”? I said the point is to realize your best work and then do another 15 years. And I don’t think he’s going to listen to me.

Let me ask you this last question: At this point in your career, what gives you the most pleasure?

When I can leverage my time in show business or the fact that I have a show and get to places that I may not be able to get to otherwise and do things. There are these scenes in Cuba where I’m in a white linen suit and I’m dancing in a parade in the middle of the street, and everyone around me is like dancing and clapping. It’s transcendent. I can’t believe I get to do that. That’s something I would have trouble imagining I’d be able to do back when I was sitting in my small room writing Simpsons scripts on the Fox lot in 1991. I could never have dreamed that I would get to do this. So, yes, my goal is to challenge myself as much as possible and just try to have fun and do things that are new to me. Because when I’m doing that, I feel like I’m 19 years old, and I have the sexual prowess of a 19-year-old.

So I’ve heard. And then next week you’re going to Iran, is that right?

I’m going to go to Iran and straighten things out there. I’m going to the Aleutian Islands. We’re going to do a show underwater next year. And then it’s to space. We’re going to go to Jupiter; it’ll take me about 15 years to get there.

But we’ll have aged 80 years, so your show will be off the air by the time you get back.

Yeah, Matthew McConaughey explained all the physics behind this to me after Interstellar, and I completely understand it now. Thank God for McConaughey.