Conan O'Brien on Cuba: Rolling Cigars, Watching 'Gilmore Girls' in Spanish, and Finding a Cuban Andy Richter

Shortly after President Obama announced that the United States would begin normalizing relations with Cuba after a 53-year blockade against the Communist country, Mike Sweeney, the current head writer of Conan, suggested on a whim that they should be the first American late-night show to visit the island since the 1960s.

He wasn’t being all that serious, but the idea struck a chord with the 51-year-old host, whose deep reverence for late-night TV was activated by Sweeney’s suggestion.

“I had this very clear memory of being at the Museum of Broadcasting like 20 years ago, back when you needed a Museum of Broadcasting,” he told a small group of reporters last week. “Jack Paar went to Havana after the revolution but before the embargo and featured it on The Tonight Show. And the minute I heard that, I went, ‘We’ve got to go right away, because we don’t know what’s going to happen.’”

O’Brien turned to his loyal producer, Jeff Ross, who began to explore how he could possibly get a ten person TV crew into a country that has an image-conscious government and a number of travel restrictions still stacked against it. Wanting to keep the trip under the radar, Ross didn’t tell the Department of State or even his bosses at TBS, lest a “government relations person at [TBS parent company] Time Warner says, ‘What, are you crazy? You can’t do this!’”

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Ultimately, they got an invitation from the Cuban Ministry of Culture. The show sent the crew ahead of time, from Los Angeles to Toronto and on to Cuba, and later, Ross and O’Brien took a chartered jet from Miami. When the host and producer landed, they found themselves lacking the proper documentation needed to enter the country, thanks to some miscommunication with the production company that had promised to secure their entry. Without any Internet access, O’Brien and Ross had the creeping suspicion that they might be “completely f—ked.”

Luckily, he had the smalltown drama of Stars Hollow to distract him from the international hot water he may have just landed in.

"In the corner [of the airport wing where they were stuck] was a television and it’s showing Gilmore Girls in Spanish,” O’Brien said, laughing. “I had this minute of comfort, so I wandered over to the TV and I’m looking at the Gilmore Girls and it’s an episode where Rory decided to leave Yale. Edward Herman’s upset and people were like she can’t leave Yale, it’s her dream, and the mother is upset. And I’m looking around and these Cuban people who could give a shit whether Rory leaves Yale or doesn’t leave Yale.”

Ultimately, everything was hammered out, permitting O’Brien and Ross to enter the country, where they would stay for four days.

"I felt really strongly that I do not want this to be a snarky American comedy take,” the host said. “I don’t want this to be political, I very much want this to be — a lot of my remotes are me as a fish out of water, the joke is usually on me — so I want to go as a comedian who is going as himself and I want to make the Cuban people laugh and meet them.”

They shot around as much of Havana as possible, using a process O’Brien called “planned winging it,” which meant picking out locations and then trying to find locals who would play along with a giant, gangly ginger man in a white linen suit.”We wanted to have as many experiences as possible, so there’s a lot of walking around just talking to people,” he said. “I tried to learn salsa, tried to learn to dance to authentic Cuban music. So we had different setup. I got a lesson in Spanish slang from a woman who is an expert. I actually performed in a club at one point.”

O’Brien and his crew stuck a microphone on a cafe table and made it his desk, asked a band of three women to be his house band, and even found a Cuban version of Andy Richter “who I actually had more chemistry with.”

Other segments included spending time learning to roll cigars and eating at a paladar restaurant (where he was greeted by a photo of Rob Schneider, of all people). The restaurant was at the top of a crumbling old building, which line the streets of Havana.”It’s a beautiful city, the architecture is crazy, and the people are vibrant and it’s got a lot of life to it, but man, everything is crumbling,” Ross said, while O’Brien noted that he suspects big change will be coming to the Cuban capital soon.

“There’s a part in the show where I come across this really beautiful street, these old colonial buildings, and I look behind me and I say, ‘One thing that’s strange is that three years from now, that’s going to be a Baby Gap, and that’s going to be three Footlockers stacked one on top of the other, and as I say it, we’re putting those things in [digitally],’” he explained. “It’s the good news and bad news. Their lives are going to change for the better, and then there are going to be some things that are lost.”

The citizens there are eager for change, they said, and were quite curious about how Americans felt about them. Canadians, meanwhile, often visit the island, to the point that while O’Brien wasn’t recognized by any Cubans, he found himself taking a lot of selfies with our neighbors from the north.

For the most part, the ten-person crew was left alone by the government and allowed to roam the city as they pleased. There was a brief incident at a grocery store, when the owner demanded they leave; technically, he was required to get permission from the government any time a camera crew entered.

O’Brien said that he’d like to do more traveling, and could see travel-based episodes and shows being a bigger part of his future as his career presses on; he’s been a late-night host for 22 years now, and hinted that he was looking for ways to challenge and push the format — and even explore new formats altogether.

“At one point when my career morphs again I could see doing remotes in high definition from different parts of the world with more of a comedic bent,” he said. “I love travel, I love exploring things, and I love making people laugh in another culture. That was the most satisfying thing of this whole project, just getting people to laugh who may not even speak much English, don’t know much about our culture, but they understand this guy not being able to make a cigar or not being able to play music with the special beat.”

The special Cuban episode of Conan aired Wednesday, March 4 at 11 p.m. on TBS.