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Conan O'Brien in Cuba: 'All I want to do is try and make these people laugh'

Conan O'Brien stars in his own parade through the streets of Havana.
Conan O'Brien stars in his own parade through the streets of Havana.
Team Coco
Conan O'Brien stars in his own parade through the streets of Havana.
Conan O'Brien: Our man in Havana.
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When David Letterman retires later this year, Conan O'Brien will become the longest-running host in late night television.

Now in his 22nd year in the host chair, O'Brien is looking to push the boundaries of the typical late night talk show form. After President Obama announced changes to the diplomatic relations with Cuba late last year, O'Brien and his team had an idea: they would take the show to Cuba.

The result is a special episode shot over four days in Havana, which airs on TBS on March 4th. Conan attempts to learn the art of cigar rolling, he dances salsa in the streets and, as he puts it, "see if I could get them to laugh at my idiocy."

The Frame's host,  John Horn, spoke with Conan about bringing his particular brand of comedy to Cuba, the massive changes in the late night landscape, and whether he has any advice for outgoing "Daily Show" host Jon Stewart.

Interview Highlights:

If this late night thing doesn't work out, have you considered going back to Havana and opening the first Auto Zone car parts store there?

You know what, I could clean up. I could do very well. I also think I would be a very popular salsa singer and rumba dancer, so I have so many career opportunities in Cuba that I no longer fear for my career here in America.

You began your late night career 22 years ago. How much of this trip was part of a way to find new things to do with the form and your show?

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. At this point, you're just competing with yourself. I’ve always felt like I just want to push the envelope. I want to try things and that gets harder to do as you're around longer. The minute we realized, Hey maybe we can get into Cuba and be the first late night talk show to be there in like 50 years and maybe find some stuff and have an adventure, it was thrilling. The whole thing was thrilling from the planning stage to actually doing it. 

When you first floated this idea to the bosses at TBS, what did they say?

We didn't actually tell them. We sort of kept it on the down low. Then we told one guy, pretty much, that we were thinking about 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. So we decided better to beg forgiveness than ask permission.  

Do you think you could have pulled this off with a network like NBC?

That's a good question. There are certainly advantages to being on Turner because they let us do pretty much anything we want to. I don't think Turner has ever said, Hey, we'd rather you didn't do that. I like to think we show common sense. But they've been terrific partners in that they literally let us do anything we want to. I don't know if we could have done this at NBC. I think we may have been able to do it, but certainly it would have been a little trickier in terms of keeping it secret, because it's a much bigger bureaucracy. 

Obviously, relations between the United States and Cuba are changing, but as a comedy show what did you think the potential for content and comedy and creating something that wasn't just in Cuba, but actually about something?

Well, it was important to me that there be no snarkiness. I wanted this to be completely devoid of that. I think one of the advantages of my comedy fitting in a situation like this is I like to make fun of myself a lot, especially in remote segments. I like the joke to be on me. So I wanted it to be sweet, I wanted it to be really funny and have belly laughs in it. 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 is try and make these 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  sort of as a good ambassador, but also see if I could get them to laugh at my idiocy. Maybe that's the common language we all speak: whatever our differences, most people find me ridiculous. 

Did they actually laugh? What played and what didn't play?

They really did. What's good is that the key to something like this is just go with it, you can't be in control. I get there, I wander around, I'm with a camera crew, the government in no way — I don't think they are aware we were there — stopped us from doing anything. We tried to see as much of Havana and film as much as possible. So what really played [is], I'm a very physical comedian so that's kind of a universal language. Whenever I'm trying to dance or trying to sing or trying to speak Spanish to them, they're laughing already. I tried to dive into their culture, I tried to make Cuban cigars at an authentic Cuban cigar factory where they hand make them. I get the help of these different women to try and show me how to do it and that ends disastrously, but they're laughing. 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 in the morning. But they're all laughing at me, so I think that is the value of what we were doing. We saw so much, we were there four days, but we shot pretty much continuously. I think I meet about 150 different people, and we somehow managed to get it all into the special, which is nice. 

How did you introduce yourself to people? Did they have any familiarity with who you were, what the show was about?

The people who knew me there are tourists from other parts of the world. There aren't a lot of Americans there, but there are mostly Canadians, and Canadians are well aware of me [and] my show, they've been watching it for years. As far as Cubans and the Cuban people, they didn't know [me]. There's a segment where I walk along the ocean front and I'm showing young people, these young couples and kids who are all sitting on the sea wall, I'm showing them my show on a tablet and I'm trying to tell them this is what I do. Of course, it's just clips of me acting like an ass on television. I get a great variety of reactions from them laughing and saying, Sure, that could be good, to just staring at it and thinking, OK do we really want to be involved with this country? So that was the best I could do was tell them I'm a comedy star. I actually did tell a number of them that I'm the biggest star in America. 

What surprised you the most about the country? We all have an image in our minds about what Cuba is like, what the people are like. 

When you grow up in our culture and you're in our culture constantly — most of the capitalist countries around the world — you forget how much advertising you see everywhere. We're just so inundated with advertising we don't even notice it. When you go to Havana one of the first things that struck me was the music and the people and it's so colorful. In a state-run economy there are no ads anywhere. You might see some propaganda, but even not that so much. You walk through central Havana, you see these beautiful old — I mean they're dilapidated, some of them are practically in ruins, but they're beautiful — colonial, art deco, neoclassical buildings, and what you notice is [you're] not being bombarded with signs. We address that at one point in the show, we try and imagine a Cuba, what it will look like in five years after it’s opened up to American commerce, and it's kind of bittersweet. It's going to be a bunch of Outback Steakhouses and Lululemons. I'm going to get very zen on you for a minute, but whenever you gain something you also lose something, and I think that that's going to be a complicated process for Cuba. 

You took this trip at a time when there's amazing amounts of change in late night. What goes through your mind as a host when you're in the middle of that much change?

It's always about running your own race. So many of these shows are so completely different from mine. I think, 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. I don't know what 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. 

When I came on the air, Arsenio [Hall] 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. And I just think about my body of work. I haven't given it that much thought, to be honest with you, about who's doing what. It seems like pretty much everybody's carved out their own niche at this point and it seems like we're past the day [when] 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 everybody's show is so different and it seems like people have realized in the modern era, OK, there's 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?

I think he's figured it out. I went on his show [last week] and his whole thing is this attitude of, I want to get out on top kind of thing. And I said, "What if farmers had that attitude? What if farmers said, Hey, I had a really good crop so I'm shutting it down now"? The point is to realize your best work and then do another 15 years. I don't think he's going to listen to me. I think he's going. 

At this point in your career, what gives you the most pleasure? What keeps you fresh, what keeps you excited?

I think [being able to] leverage my time in show business, 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 dancing and clapping and it's transcendent. I can't believe I get to do that. That's something I'd 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 my goal now is to challenge myself as much as possible and just try to have fun and do things that are new to me. When I'm doing that I feel like I'm 19-years-old — and I have the sexual prowess of a 19-year-old. 

Conan in Cuba airs Wednesday, March 4 on TBS at 11 p.m. (ET/PT)

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