TBS

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."

That desired outcome could be debated. To the general confusion of his Cuban hosts, O'Brien revels in declaring his stardom over and over again only to find the crowd either bemused or unamused by his exhortations. His prowess at physical comedy, manically displayed as he tries to jam with a Cuban salsa band or learns how to dance, seems to fall short with onlookers. However, when he later visits a cigar factory and produces a package of White Owls, a drugstore brand of cigars that he dubs America's "finest cigars," he finally gets a genuine chuckle or two. (While a majority of Americans favor the normalizing of relations with Cuba, the ones that still oppose it may not be pleased.)

For an American crowd, however, there were some funny moments. Watching the beautiful sunset over Central Havana, O'Brien quips: "If Hemingway were here, he'd probably write a beautiful sentence about it. And then punch someone."

There were also a few spare moments containing prods at the idiosyncrasies of Cuban life. At a grocery market, before an employee informs him that he can't film there, O'Brien marvels at how each shelf is lined with exactly the same product, a departure from the endless bounty of brands at American shops. Later, before dining at a classic Cuban paladar, or family-run restaurant, O'Brien remarks on the decor, which includes statues of Jesus and Karl Marx beside each other. Under his breath he grumbles about Marx's infamous lack of affection for organized religion. In other words, funny for one side, but probably not the other.

Near the end, he mumbles toward a message. In a voiceover like the one he uses at the beginning of the special to deliver an anodyne reading of the history of the American-Cuban freeze, O'Brien wishes aloud that "we'll soon begin mending the long-broken relationship between our two countries." The implicit hope is that it starts with comedy.

If Conan in Cuba is any indication, the better catalyst for a Cuban-American mend may be baseball, which leaves less wiggle room for cultural dissonance. In his 1984 Atlantic story on the Cuban-American baseball divide, Bruce Brown characterized the game as a "too true a receptacle of human emotion to lend itself to such politicization."

As we noted last week, Tony Clark, head of Major League Baseball Player's Association recently let it slip that the league had considered playing a few exhibition games in Cuba earlier this year to hasten the thaw. Ultimately, they decided it was too soon. It may still be too soon for comedy as well, noble receptacle though it is.

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