Conan O’Brien’s Trip to Cuba: “It was one of the greatest experiences of my life!” in OutlooK-12 Magazine

by Ricardo Castillo in

For more than 50 years the island of Cuba has been forbidden fruit for the American palate. Travel bans and a lack of diplomatic relations has cloaked Cuba with a veil of secrecy and mystery. As with all engaging mysteries, there are perceived villains and heroes on both sides of this issue who have stirred the pot and heated up the rhetoric. However, recent events and the passage of time have made reconciliation between Cuba and the United States more likely than not. 

The seemingly invincible but aging Castro brothers are mortal, after all, and not immune to the impact every passing day has on their iron-fisted grip on this island. On December 17, 2014, President Obama changed international rules of engagement when he announced his intent of having the US establish diplomatic relations with Cuba. While serious talking heads were debating the White House pronouncement, one not-so-serious talking head sprang into action.

Comedian Conan O’Brien, the host of “CONAN” on TBS, with the help of his Team Coco quietly
made plans to become the first American late night talk show host to visit and film in Havana
since Jack Paar interviewed Fidel Castro on his Tonight Show in 1959.

The behind the scenes preparation for bringing “CONAN” to Havana was no easy task. After
considering the possibility that asking permission to film might tie them up in bureaucratic red
tape and kill the project, the decision was made to engage in “guerilla filming” on the streets
of Havana.

 “It used to be easy for Americans to visit Cuba,” O’Brien explained to his viewing audience.
“In the 1940’s and ‘50’s it was the Las Vegas of the Caribbean.”

Now, however, producing a show there would be different. Cuba is a country with many complicated social and political problems. So this process wasn’t easy. O’Brien and Team Coco came with a game plan.

 “I kept the purpose of my visit simple: to meet the people and try to make friends,” said O’Brien. “We wanted to ‘run and gun’ and stay under the radar. We didn’t want to be too conspicuous. We rolled into sites pretty quickly and we shot.” 

As if that was not daunting enough, Team Coco was faced with the challenge of coming up with a talk show desk set similar to “CONAN’s” regular TBS set. 

“The thing with the Cuban government is that if you start setting up something people will come right over and demand your papers,” O’Brien recently told Team Coco’s video chat participants. “They ask are you a reporter? Are you authorized to film on this street?”

As O’Brien was scouting locations to use for that purpose, he came upon a sidewalk café on a narrow street, which just happened to have a 5 member women’s band called Dava playing there. There was one café table outside, which Team Coco commandeered by “throwing some
money at some French tourists who were using it” for O’Brien to use as his talk show “desk,” dressing it up with an old fashioned microphone someone found in Havana. So with a house band and desk in place O’Brien opened his twopart “CONAN” Cuban special by strolling out into view on this same narrow street, wearing a fedora and a light linen suit. Once he sat down at his make-shift talk show desk, he was ready to introduce all of America to the Cuba he had discovered. O’Brien was determined to give as accurate and in-depth a portrait of Cuba and the Cuban people while cramming as much entertainment value as he could into four days
of filming.

“We wanted this to have a sensitivity and sweetness to it, so we didn’t pick solely hard hitting comedy. We didn’t want to be snarky. We really wanted to respect the people and the culture,
and I think we achieved that goal. I feel lucky that we had the idea and the team to pull it off,”
O’Brien revealed on a recent online chat. “All the moments were real with people who were funny and comfortable in their own skins. We couldn’t set this up. We didn’t use stock footage. We had these huge cameras we used. We pretty much shot around the clock. Cuba is a visually stunning place to shoot and we wanted to capture it. It was magical. It was a perfect snapshot in time to go there.”

On his stay in Cuba, O’Brien filmed all over Havana, including inside a cigar factory, dance studio, nightclub, rum factory and among locals at a popular promenade. The euphoria that was building in Team Coco for accomplishing what had been impossible just weeks earlier was stopped in its  racks, however, as they began to make plans to go home.

“It started with less than 24 hours before we were supposed to return home. Our executive producer Jeff Ross was notified that a news outlet had heard probably by tourists that we were there, and they were going with the story.” O’Brien admitted. “We asked them to hold it until we at least got off the island with the footage, but they said they were afraid someone else had it, so they were going to go with it. And we were nervous. We decided to make multiple copies of what we shot on drives and tablets and laptops. We figured if any of it was stopped by customs we had backup copies that might make it through.” Luckily, the film made it back to the United States without much incident. 

It’s clear that O’Brien was moved by his exposure to Cuba and its people.

 “I hope we will soon be able to begin mending the long, broken relationship between our two countries. Despite the differences in our governments, the human level is so much we share. Laughter, music, the love of good food and sheer genius of rum in a box [a drink popular with young men on the promenade]. I was in Havana four days. It was one of the greatest experiences of my life,” O’Brien told his TV audience. “The people here are talented, they’re funny, they’re vivacious, they’re warm. People are anxious for economic relief. They need it. They very much want to get to know us and do business with us. That was the strong, strong, strong sense we got just talking to people. I was very happy to see that you can cross barriers. I’ve always noticed that if you’re humble and sweet you can connect to people with humor. I can’t say enough good things about the people of Havana and Cuba, and I can’t wait to go back.”

Meanwhile, those who wish to experience Cuba through O’Brien’s eyes can view the entire special, scenes from the episode or behind the scenes information at