“Hey, who’s paying for this?” asked Conan O’Brien as he entered an Italian restaurant in Midtown Manhattan, where about a dozen journalists were sitting in front of appetizers, waiting for him to arrive. The purpose of the luncheon was to hear, first-hand, how O’Brien became the first U.S. late night talk show host to shoot an episode from Cuba since the embargo began. The episode will air March 4.
Those familiar with O’Brien’s popular remote segments know that his “fish out of water” approach to new cultural phenomena can be hilarious. After President Barack Obama’s announcement that the U.S. was working toward ending the embargo with Cuba, head writer Mike Sweeney casually suggested that they go there. O’Brien took the idea seriously because he remembered when then-“Tonight Show” host Jack Paar shot an episode from Havana after the revolution ended but before the U.S embargo in 1962.
“So the minute I heard [Sweeney suggest] that I was like, ‘We gotta go, and we gotta go right away, because we don’t know what’s going to happen,'” O’Brien said.
And with that, O’Brien and executive producer Jeff Ross began planning a completely under-the-radar trip to Cuba for four days over President’s Day Weekend to shoot a 1-hour special completely from Havana.
“I wanted the whole thing to be from Cuba, not a cutaway [from California],” O’Brien said. “We asked a cafe if we could borrow their cafe table, then we put an old microphone on it. There was a band of three or four Cuban women playing and I asked if they would be my house band. Then we found a guy to be Cuban Andy — who I actually have better chemistry with — and we shot the wraparounds there, just to give it that sense.”
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“We’re used to only thinking about comedy. For this one we thought: we want there to be funny moments, we want there to be really sweet moments and moments of connection, but we really just want to get the palate of Cuba,” O’Brien said. “That was the big difference to me. I’ve only, for 22 years, been aggressively pursuing what’s funny, and this was a different agenda.”
O’Brien’s career as a late-night host could morph into something closer to what Anthony Bourdain does, but with a comedic bent rather than a foodie one. He explained that in a world where there are more and more talk shows every year, he feels more of an impetus to keep changing and “do something radically different than what [he] did 10 years ago.”
“I love travel and I love exploring things and I love trying to see if I can make someone laugh in a different culture,” O’Brien said. “That was the most satisfying part of this project, just getting people to laugh who might not speak much English, don’t know much about our culture, but they understand this guy not being able to make a cigar.”
O’Brien hopes to somehow get a copy of the finished special down to Cuba after it airs so people can watch it, in hopes that his portrayal of the Cuban people helps to heal relations between the two countries, even if the special was done in the name of comedy.
“And maybe it’s not a bad form of diplomacy,” O’Brien said. “It is a universal language, if you can get it right.”
