A Comedian in Cuba

It's a comedic format familiar to Conan O'Brien and his production crew: Leave the confines of the studio and travel to a remote location to film the gangly late-night star as he attempts to win over the local population with his self-deprecating charm and offbeat humor. So when President Obama announced his plans to improve U.S.-Cuba relations last December, O'Brien knew he needed to film in Havana, before any other television show.
And so O'Brien and a crew of 10 visited Cuba's most famous city for four days in February, becoming the first American late-night show to film in Havana since Jack Paar's famous Fidel Castro interview in 1959. Whereas Paar set up a replica studio atop the Hotel Habana Libre, the O'Brien special, which aired March 4 and can be watched on the show's website, is purposefully organic, with Conan and the crew filming all around Cuba's capital city.
"We also had this agenda from the beginning," says O'Brien. "We wanted this to have a sensitivity and sweetness to it. We did not want to be snarky, and we really wanted to respect the people and the culture."
Instead of appearing in makeup and suit behind a desk, O'Brien is seen in street clothes, gesticulating like a madman until he gets a smile. Whether he's speaking with teenagers on the Malecón, singing with a salsa band, learning the rumba or pretending he's intoxicated during a tour of the Havana Club rum museum, the Cuban people laugh with him. (Or, at least, at him.)
Of course, O'Brien visits a cigar factory; La Corona to be specific. There he grabs the lector's microphone and holds up a pack of machine-made cigars. "These," he deadpans in broken Spanish, "are the finest cigars we make in the United States." After, he learns how to roll his own Habano. While the inspector doesn't approve of his cigar, she can't help but smirk when he holds his poor attempt up to his mouth and gives it a shake, á la Groucho Marx's signature cigar move.
O'Brien doesn't just succeed in his goal to be funny but remain respectful to the Cuban culture, he excels at it. Perhaps he should add another title to his many: writer, actor, talk show host, and now, America's first cultural ambassador to Cuba.