Conan O’Brien’s history-making Cuba mission: ‘Make them laugh’

On Wednesday night, TBS will air a special episode of “Conan” filmed entirely in Cuba, making it the first American late-night show to broadcast from the island nation since a U.S. embargo was imposed near the height of the Cold War, in 1962.

Host Conan O’Brien will follow in the footsteps of Jack Paar, who interviewed Fidel Castro at the Havana Hilton for “The Tonight Show” in 1959. Though O’Brien did not interview any heads of state, in some ways his mission was even more daunting.

The comedian and a team of about 10 writers, producers and crew members flew into Havana over Presidents’ Day weekend with no real plan and only a letter from the Cuban government (their visas were temporarily lost). It was the kind of guerrilla operation one might expect from, say, “Vice” and not a seasoned late-night veteran.

The four-day Cuban voyage also kept O’Brien from attending the “Saturday Night Live” 40th anniversary celebration in New York last month. “Everyone was wondering why I wasn’t there. I was like, ‘Well, I have something I have to do,’ ” a sleep-deprived but enthused O’Brien said Tuesday morning after a late night putting finishing touches on the special. Here he opens up about his groundbreaking Cuban adventure.

After more than 20 years doing a late-night show, it must have been an exciting challenge to take on a project like this.

It was incredibly invigorating. I think we’re almost at 22 years now and thousands of hours and we always have tried to push it and find ways to make ourselves happy and make me happy. But the biggest challenge is fatigue, and I don’t mean physical fatigue. I mean you can start to take it for granted. If you’re in late-night TV for a long time and probably any job, it’s a little akin to driving on the highway for a long time and you can become hypnotized by the white lines. You’re driving and you’re doing a fine job and everything seems OK, but you need to keep pulling the car over and having a lot of coffee and smashing your head up against the side of the road and get off road and really wake up and challenge yourself. I’ve tried to do that a number of times throughout my career and this was just fun.

We didn’t really tell anybody at Turner we were doing it. We put it together on the down-low and then we went to Cuba and didn’t really know what I was going to find. I had a good sense of what I wanted the tone to be. I wanted it to be snark-free. I didn’t want to go there and be the snarky comic in the foreign culture who’s laughing at it. I very much wanted it to have a sweetness to it and I think that’s one of the ways I was maybe well-suited to that. A lot of my comedy, especially the remote segments, the joke is on me. I’m the fish out of water and I’m inept at things and a lot of the laughs are at my expense. I wanted that to be the tone. I really wanted it to be as simple as I go to Havana, I want to meet these people, and I want to try to make them laugh.

I think that mission was accomplished because there’s a lot of segments where I’m diving into their culture, I’m trying to do their thing and they find me absurd. They’re laughing at me but the entire time understand where it’s coming from. It’s nice to know that there’s this universal language with this culture that’s been isolated from ours for 53 years, they understand this absurd man is terrible at salsa singing, he’s terrible at dancing the rumba, he made a terrible cigar, he got drunk on the rum tour, he looks stupid in the motorcycle sidecar because his legs are too long. And I wanted Americans to really see Cuba -- you can’t really say Cuba it was just Havana, that’s all we had time for. It’s obviously quite different once you get outside Havana but this is what we could do.

How long were you there for?

Four days.

It sounds like the special will not follow the usual format.

No, it doesn’t. We do a nod to the talk show. At one point while we were there we found a street that we liked and we asked a restaurant if we could borrow their cafe table. We put an old microphone on it, there were three women in the bar next door. They were incredibly charismatic young women who were just playing Cuban music. I asked if they would be my band. They said “OK.” I found a guy and I asked if he would be Cuban Andy. He said, “Sure.” Then what I do is I throw from that desk and then I end the show there.

And the rest of the show is I’m out and around so it’s obviously not me sitting and interviewing guests because I thought that has no value. I go all the way to Cuba and then interview the cast of “Cougar Town.” “Great job, Conan! Really good!” We decided, I wanted as much of the special to be me in and around Cuba and really going everywhere and trying everything and eating everything and putting myself out there. The only convention is the top and the end of the show, and maybe in the middle, just me sitting at the desk with the microphone to remind you that yes, this is a late-night talk show.

It’s funny, it has a really sweet feel to it. While I was sitting there at the desk, people were wandering by while I was doing the show. A little kid walked by. That’s what I love about it. A lot of people behind me staring at me just wondering, “What is that idiot doing?” So it doesn’t have any of the pomp of, like, a big show.

How did you explain yourself to people and get them to participate?

I would keep it pretty simple, I would tell them I have a television show in America. One of the kids said, “It’s a lie. He’s lying.” And then I take out my iPad and we show them my show and we get some interesting reactions. I tell one group of people that I’m the biggest star in America. And I told some people that I’m Ryan Gosling. I just thought, why not? I learned the phrase for “I’m the biggest star in America.” And I also learned the phrase for “And please don’t check into that.”

It was nice because what I’m hoping really comes across in the special is obviously there’s this incredibly complicated history, the politics are dark and there’s a lot there that is very fraught -- “fraught” is one of my favorite words. What I wanted to do is say OK, untangling that is going to be chaotic and it’s going to take a long time and be difficult, this is just about me meeting people and trying to make friends and doing it with humor and generosity of spirit and I do think we accomplished that.

Where did you stay?

It’s funny, we found a guy who was Canadian who actually does some production work in Cuba. He helped us work out how we get into the country, where we could go. We had a few meetings with him. He put us up at the hotel that I think is owned by a Spanish company, Melia Habana. It’s down by the water and that was pretty fascinating because we take Internet access so much for granted in this country. People can be in the middle of a national park and they only have three bars instead of six and they’re angry at God and America. Here, there’s nothing.

The one thing they did have at the hotel was WiFi so I could at least tell my wife, I’m here, everything’s fine, everything’s cool. To get it you have to enter in a 35-digit code and then a 20-digit code, and that gives you access. And it says, “You now have access.” I would send one email and it would log off. I had this sheet of paper with a ridiculous number of digits on it. You just notice things like that.

It’s very much a different world. I loved the lack of advertising, there’s no signage anywhere. I’d heard there’s no crime and it looked to be very safe. We didn’t have anybody with us, it’s not like we were being escorted to, like, the good areas. There’s a lot of Havana that is very beautiful, as it is now, even in its sometimes dilapidated state. It’s really a mixed bag, we address it at one point in the special. At one point I’m talking in front of all these old buildings and I said it’s a little bittersweet because in three years that’s going to be a Lululemon, that’s going to be three Foot Lockers, one on top of the other, that’s going to be a Burger King. And we actually used special effects to put them all in behind me.

It’s kind of funny but it’s also ... if this process continues of normalizing relationships, what will this country be in five years? There are a million questions. Will these people be happier? Everybody I talked to, they’re very interested in establishing economic relations with the United States. They need the money, they want the money, they’re very excited for it to happen, and they’re also very excited that most Americans are behind it.

Did you find that most people were happy to talk to you, or were they reluctant?

All the stores are state-run and I just walk into one store and there was a guy who was very nervous about us being there. So we blurred his face, and that was the only time I sensed apprehension. A couple of times there were people that shied away from the camera but for the most part I was surprised. People were very happy to come up and engage and talk and find out what I was doing. Like I said, there was just a universal kindness and warmth to the whole experience.

What did you learn about the Cuban sense of humor?

They are very quick, very sharp and they are more than happy to laugh at me -- which I thought, Great! This is a good sign. I come from a country where people are more than happy to laugh at me and now we’ve come to Cuba and they’ve been closed off from any late-night host in 53 years and they immediately understood that I’m a figure of ridicule and I was like, “Perfect, this could be OK.”

Having traveled to Cuba, do you have thoughts about taking the show to any other closed-off countries?

I would love to. Obviously Cuba was a special opportunity and it was perfect to go there and it’s hard to find the right conditions in another country. But I loved putting myself completely out of my element. I think I’m at my best when I almost have no control. I really do believe that as a comedian. When I have too much control, there’s no fizz in the champagne. It’s a really funny push-me, pull-you, yin-yang. Comedians like me are desperate for control, but sometimes we’re at our best when we have no control. I’ve usually been at my funniest when I have little preparation, I’m just tossed into a situation and it’s chaotic and I’m the fish out of water and I’m the underdog. That’s when things tend to sparkle. I’m eager to do that again.

A show from Guam? Who knows? Iran? Possibly, we’ll see. I didn’t get to see Netanyahu’s speech yet. There’s a lot of places I’d love to go. It feels, it’s a good feeling after all these years to do something and almost feel like you’re a novice again. After 22 years of doing this, to feel really excited to screen this for an audience [Wednesday] and then get it on the air is great.

Can you talk about the origins of the special and the process of putting it all together?

Obama announced in December we were going to begin the process of normalizing relations with Cuba. I think it was two days later my head writer said, “Oh, it would be great if we did a show from Cuba.” The minute he said it, I said, “OK, that’s happening. We have to do that.” We looked at our calendar and initially it didn’t look like it would be possible to go to until April. I was very anxious about we’ve got to go now. Things could change, conditions could change. If we’re going to do it, the moment is right now.

We contacted a producer who is from Canada but works with some European production companies in Cuba. He said, yes this can be done, it would be great to get a letter from the Cuban government accepting me as part of a cultural exchange. We got that. We’re not really sure what that meant, if it meant we could bring cameras. We played it all pretty fast and loose. We put it together very quickly, we taped some shows in advance and moved our schedule around so that we could get there as quickly as possible. We decided we didn’t want to tell anybody, we told one person at Turner and we told everyone who was going, “just don’t talk about it.”

We sent our camera crew ahead first and they got in. I came second with my producer Jeff Ross and my head writer Mike Sweeney. We went in and we had, when we first got to the airport, we showed all our papers. The guy smiled at us and said, “No.” We sat in the airport for an hour and a half, two hours. Our cellphones didn’t work, we didn’t know anybody there. I couldn’t see our plane anymore and I didn’t know what was going to happen. There were a lot of discussions back and forth and somehow it got worked out, and I don’t even know what that means. We got into the country and we started shooting immediately because we just didn’t know. Are we going to be asked to leave, is this cool?

Nobody accompanied us, nobody told us you can’t go here and you can’t go there, so we did whatever we wanted. Then I think the story broke just about 15 hours before we were going to leave. Then we were worried there might be a problem getting our footage out, so we divvied up the footage, we sent it back a couple of ways.

Do you expect other talk shows will follow your lead and visit Cuba?

I think “The View” will be there in three days. Then the embargo will go back up again. “The View” is going to ruin this whole thing.

Follow @MeredithBlake on Twitter.

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UPDATE

6:53 p.m.: The introduction of this story was updated to reflect editing changes made for the print version of this interview.

This story was originally published at 1:39 p.m.