Conan O’Brien has sat behind a desk and hosted a talk show for more than twenty years, but his funniest moments continue to come when he leaves the set and puts his gangly six-foot-four-inch frame and rooster head out among the people. The recurring joke—whether O’Brien is visiting Houston to demand that “Late Night” get a better time slot or travelling to Ireland, Germany, or Australia—is seeing his aggressive self-regard butt up against the indifference of the men and women he meets on the street.
On Wednesday night, on his TBS show, O’Brien aired a special that was assembled from a recent four-day trip he made to Havana, in what has been marketed during a press tour this week as the first time an American late-night host has shot an episode in Cuba since the U.S. embargo began, in 1962. Fitt...
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