The last time an American late-night television host broadcast from Cuba, it didn't go over so well. The year was 1959 and Jack Paar, the iconic host of The Tonight Show, interviewed Fidel Castro from Havana. Needless to say, there was some pushback given that Castro's socialist revolution had ousted Cuban President Fulgencio Batista one month earlier. On Wednesday night, just a little over two months after President Obama announced he would seek to normalize ties with Cuba, Conan O'Brien's sojourn to the island nation aired on TBS.
Unsurprisingly, the Conan in Cuba special was specifically designed to elicit little of the controversy that Paar did, instead featuring the gangly comedian taking (mostly) the safest route possible throughout a fifty-minute square-peg-in-a-round-hole routine. O'Brien dances rumba, flexes some flabby Spanish muscles, rolls coronas in a cigar factory, and drinks rum, all in the service of treading lightly over the political discord that characterizes half of a century of American-Cuban relations.
"I felt strongly that I do not want this to be a smart, snarky American comedy take," O'Brien told USA Today. "I don't want this to be political. A lot of my remotes are me as a fish out of water, the jokes are usually on me, I want to go as a comedian making fun of myself and make Cuban people laugh. In that regard, I think I was successful."