On Wednesday’s show, Conan O’Brien will be found in a familiar place: behind a desk. Or, rather, what he describes as a borrowed cafe table. In Havana, Cuba.
But for most of the hour (11 p.m. EST on TBS), Conan will find its host footloose and fancy-free, airing a talk show from this nearby but isolated island country for apparently the first time since Jack Paar took his own late-night show to Cuba in 1959.
Conan in Cuba, still being edited, was unavailable for preview. But in a chat with reporters recently, O’Brien listed a few highlights: He tries to learn to play authentic Cuban music and how to rumba. He visits a cigar factory where 400 virtuosos make cigars he calls “works of art.” (He’ll try to make one, too.)
He tries to supplement his 8th-grade Spanish vocabulary with instruction in Spanish slang.
And he takes a meal at an out-of-the-way paladar (a family-run restaurant in a Cuban home), where he revels in having made a dining discovery no other Americans would likely stumble on — then spies a photo on the wall signed by comedian Rob Schneider.
Most important to his mission, O’Brien mingles with Havana locals and takes in local sights. For an hour, his is a talk show unmoored.
The venture — springing Conan from its Los Angeles home base — began when President Barack Obama in December surprised the world by re-establishing relations with Cuba a half-century after communist rule led to estrangement from the U.S., just 90 miles away.
Having seen a long-ago tape of Paar’s historic visit just months into the regime of Fidel Castro, O’Brien said, “We’ve got to go — right away!”
“It wasn’t as complicated as I thought it would be,” said Conan executive producer Jeff Ross, who reached a production liaison in Havana. “He said, ‘Just come. We’ll get you an invitation from the Cuban government. You’ll have the run of the place.'”
The 10-member troupe went in mid-February and spent several days in the Cuban capital.
“I was shocked,” said O’Brien, “by how much we were left completely alone.”
He found the architecture beautiful but, typically, in disrepair, while “the people couldn’t be warmer and nice.”
“They’re very interested in how Americans feel about them,” he reported. “I told them Americans disagreed on everything, but in polls about whether we should normalize relations with Cuba, we are overwhelmingly in favor of it. They were happy to hear that.”
O’Brien made the trip with a clear intent, resolving beforehand, “I do not want this to be a snarky comedy take. And I don’t want to be political. I want to go as a sort of comedian who is making fun of himself and make the Cuban people laugh.
“Maybe it isn’t a bad form of diplomacy,” he said — “to send a comedian over. Maybe that’s not a bad first wave.”
At the same time, O’Brien sought to immerse his viewers in Cuba’s character.
“For 22 years, I’ve only been aggressively pursuing what’s funny, and this trip had a different agenda. There’s wear-and-tear doing [a late-night talk show] for a long time,” said O’Brien, who arrived at NBC’s Late Night in 1993 and has starred on Conan since 2010. “The only way you can keep going at a certain point is to change and grow and try different things. Stuff like this [trip] re-energizes me.”
Then, asked how much longer he might want to stay in the late-night trenches, O’Brien replied with a smile, “I think there’s gonna be a day where I’ll wake up and I’ll say I can’t think of another thing I could possibly do with this form.
“And then I’ll do five more years.”