Conan Secretly Filmed His Show in Cuba This Weekend

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Conan’s had a pretty bad run of it these last few years. After briefly occupying the most coveted time slot in American comedy, the jolly red giant found himself summarily bumped from his gig hosting The Tonight Show and without a home on network TV. It wasn’t easy to watch a talented man fall from such great heights, but like a true boss, Conan dusted himself off, dropped down a couple of dozen channels to a basic-cable rerun depot called TBS and kept doing his thang.

And now, he’s made history. That’s right, decked out in a three-piece linen suit, green paisley tie and jipijapa, Conan O’Brien followed Netflix’s lead and took his Conan show on the road to Havana. Granted, over the last month we’ve been seeing more and more U.S. news programs exploring “life on the ground” in Cuba, but not since 1959 has a late night talk show made the 90-mile hop over the Straits of Florida to the land that time forgot.

For you TV history buffs, it was actually Jack Paar, host of The Tonight Show from 1957-1962, who made that famous last trip in the midst of rising tensions between the U.S. and it’s neighbor to the south. A few months earlier, Ed Sullivan had done the same when, surrounded by submachine guns, he gave a rather giddy interview to Fidel Castro in which he compared him to George Washington.

Now, by all accounts, Conan had the time of his life sucking down Havana Club mojitos and cruising around in restored ’57 Chevys, but we do have to wonder how deep the 6’ 4” funnyman really made it into the reality of Cuban daily life. Still, one thing is for sure: the folks at Jimmy Fallon’s Tonight Show outfit will surely be scrambling to outdo this stunt (we’re assuming at this point that Letterman doesn’t care all that much.)

The episode in question will air on TBS on March 4. In the meantime we still have gems of Cuban independent cinema like La obra del siglo (The Project of the Century), Hotel Nueva Isla, and Venecia to give us a slightly more nuanced portrait of everyday life in La Perla del Caribe.