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Conan O’Brien Talks Cuba Trip, David Letterman and Dealing with Depression

With the news that the U.S. may soon normalize relations with Cuba after more than a half century, Conan O’Brien tried a little comedy diplomacy earlier this year by spending four days on the fly in Cuba, seeing the sights and interacting with the locals.

It was the first time in more 50 years that an American talk show host was allowed to visit the country. O’Brien treated the historic moment as an opportunity to do what he does best: make fun of himself for being pale and awkward.

On Friday, the Paley Center for Media in New York screened the two Cuba episodes of TBS’ “Conan,” which first aired in March. The episodes were a major departure from his usual format. They featured a warm and loose O’Brien awkwardly attempting to learn native dancing, discovering the pleasures of rum in a box, and learning key Cuban phrases from an old woman, including “does this freckle look pre-cancerous?” (Without missing a beat, the woman he asked to translate the phrase immediately said yes, and O’Brien responded with his signature exasperation.)

After the screening, O’ Brien sat down for an interview with CNN anchor Anderson Cooper, during which he explained that they visited the country, with help from a Canadian producer, with very little idea for what they would find. “This is completely improvisational,” he said. “You are flying without any kind of safety net.”

O ‘Brien talked about a segment in which he visited a rum museum, and proceeded to annoy his extremely patient guide by pestering her to stop talking about the history of Cuban rum and get to the part where he could have a drink, as an example of what he was hoping to achieve.

“I never expected the rum museum to be that funny. We almost didn’t go. It was a total accident that woman was the guide, and she was perfect,” he said. “What I like is she’s an equal comedy partner. What I found in Cuba is a country of great improv partners.

“When we decided to go, I said ‘I want this to be sweet, I don’t want this to be snarky, I don’t want the joke to be on anyone in that country, the joke should be on me,’ ” he said. “I think that we achieved that. Mostly I wanted to make them laugh. There’s a real sweetness to the people, and they were very receptive.”

The talk also covered O’Brien’s feelings about David Letterman’s impending retirement (“I feel like I’m losing my nightlight”), his comedy philosophy (“I’m always looking for the mistake”) and his approach to celebrity interviews (he always brings up the project they are working on last and spends as little time on it as possible). He and Cooper discussed their attempt to start a fake feud and the time a few years ago when Cooper visited his show to promote his book, and O’Brien wound up using the book as a coaster before throwing it off the desk, much to his audience’s delight.

During an audience Q&A, O’Brien opened up about his history of anxiety and depression ( he said that he initially resisted going to therapy and taking antidepressants as he worried it would dull his comedic edge, but found they only helped his work), and how he tried to find comedy in a country with troubling history of human rights abuses.

“It’s such a sensitive issues, and I didn’t want to delve into all of that,” O’ Brien said. “I didn’t want it to be about politics, I wanted it to be ‘Who are these people?’

“We acknowledge that there’s a dark history there, and there really is. Cuba has been a terrible place if you’re a dissident. If you don’t agree with the government, you’re put in prison. It’s been a terrible place to be a homosexual. There’s a lot about Cuba that is quite clearly very troubled and dark in the last 40 or 50 years,” he said. “We wanted to go and meet the people and find out who these people are. We wanted to communicate on the oldest and most simple level, which is comedy, and be humble myself, and make myself the joke.”

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