Conan O’Brien sat down with CNN anchor Anderson Cooper at The Paley Center for Media last week to discuss taking his comedy to the streets of Cuba this past March, the first late night host to do so in five decades.
Known for his goofy antics on screen, the TBS late night host and comedian surprised fans by taking his team of 10 writers and producers to Cuba to spend four days filming there earlier this year. The decision came after one of Conan’s head writers suggested producing a show from Cuba shortly after President Obama announced at the end of 2014 that he was working towards lifting the embargo.
In the special episode, Conan explores the land of rum, cigars, and salsa alongside locals who were “amused by the strange, tall, pale man with funny hair.” Over 2 million viewers tuned in to watch Conan insert himself into Cuban life (using his high school Spanish) and fail miserably, all for laughs. In turn, Conan admitted the Cuba episode humbled him, and was the proudest show he’s done.
Though Conan was disappointed to realize he was the last celebrity to visit Cuba (Jay Z and Beyonce beat him to it in 2013), he was determined to befriend locals and learn from them in funny, improv fueled segments. Highlights from the episode include Spanish lessons where Conan fiercely disagrees with Cuban tongue twisters, salsa dancing with beautiful women who keep him at bay, and touring a rum museum that ends in a slurred singalong. But the joke was never on Cuba or its people, O'Brien explained.
“I don’t want the joke to be on the people I’m talking to, I always like the joke to be on me and I think they sensed that,” he said. “I want them to realize. . .this man’s ridiculous.”
Conan fans know he is a master at making himself the punch line, and that he doesn't miss a beat when it comes to improv, which came in handy while filming in Cuba. With no permits, no restrictions, and very little planning, Conan’s team was able to shoot field pieces that felt spontaneous, setting out to find areas of “high probability” where something funny could happen — many times, by surprise. One segment filmed at the end of a long day (which wasn't intended to make the final cut) features Conan bantering with the camera crew on a rooftop, playfully mocking a CNN-style report where he realizes "Anderson Cooper has a very easy job."
Playful jabs aside, Cooper and Conan also discussed the power of comedy to bridge cultural gaps. Team Coco has previously traveled to Finland and Ireland, and with the success of the Cuba episode, new trips (yet to be announced) will emerge. Admittedly, locations like Cuba will be hard to duplicate due to its comedic timeliness, but Conan has more ideas for adventures and filming live shows.
“You have to keep changing it up," he said. "And I think the great thing I loved about Cuba is that I was excited, I was giddy. . .I don’t know what’s gonna happen but I love going into the country and figuring it out.”
Until he announces his next global adventure, fans can tune in to watch Conan weeknights on TBS at 11/10C.