Dressed in a white linen suit and fedora, Conan O’Brien bounced on to his set — a cobbled street in Havana — for a one-hour special on Cuba Wednesday night.
“Conan in Cuba,” which aired on TBS, was filmed during four days in Havana in mid-February and came on the heels of the rapprochement announced in December by President Barack Obama and Cuban leader Raúl Castro.
It was the first foray to Cuba by an American late-night host since Jack Paar interviewed Fidel Castro in 1959.
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For the most part, the joke was on Conan as he tried to match the swiveling hips of Cuban dancers, hand roll a cigar with unfortunate results, jam with Cuban musicians, sample too much rum too early in the day, convince kids along the Malecón that he was really a big star and to speak Spanish.
His humor was of the fish-out-of-water variety — in his case, a tall red-haired fish out of water.
“Hola. Bienvenidos a Cuba. Yo soy Conan O’Brien y lo siento pero that’s all the Spanish I can really memorize” is the way he began his show from a cafe table fitted out with a vintage microphone, two cigars and a mojito.
“As many of you know, this is a very historic time. Relations between Cuba and the United States are finally starting to thaw,” said O’Brien before launching into a brief history of Cuba and noting that in the 1940s and 1950s it was “the Las Vegas of the Caribbean.”
He asked a man sitting at a nearby storefront, “Can I call you Cuban Andy?” and joked he got on better with him than his real late-night sidekick Andy Richter.
O’Brien said his reason for going to Cuba was simple: “to meet the people and try to make friends.” After inciting a cacophony of barking dogs as he walked down a street, he remarked, “Old women love me; dogs hate me.”
He poked fun at a Cuban market where he noted that entire rows were filled with the same product, the same brand, and said the cocoon-like Cuban pay phones “enable you to make a call and get your hair permed at the same time.”
“It was important to me that there be no snarkiness,” he told The Frame radio show. “I wanted to go as a good ambassador but also to see if I could get them to laugh at my idiocy.”