OPINION: What we can learn from Conan’s hilarious Cuba trip

By John Irwin

Conan O'Brien in Cuba. (Courtesy: TeamCoco.com)
Conan O’Brien in Cuba. (Courtesy: TeamCoco.com)

I’ve considered myself a member of Team Coco since the 2010 Tonight Show debacle, so when I won the opportunity to screen Conan O’Brien’s special Cuba episode I immediately booked my plane tickets to Los Angeles.

After all, this episode, which aired last night, is somewhat of a big deal. President Barack Obama announced earlier this year that his administration would be working to ease the embargo the U.S. has held on its island neighbor for half a century. That announcement, Conan told the screening audience, was the impetus for wanting to film in Cuba.

The goal of the episode, Conan said, was to entertain but also to highlight and document the country’s culture and look as change looms on the horizon.

As he told CNN’s Jake Tapper in a Wednesday interview, laughter can be the “greatest kind of diplomacy,” especially when that humor is at the expense of himself.

“Don’t go in as the scary imperialist,” he said. “Send Conan in first and make them ridicule me. That sort of softened up any of the tensions that might’ve been there.”

(Note: Recording devices were banned at the screening I attended, so any direct quotes in this post are not mine.)

Conan’s signature brand of self-deprecation, absurdism and cerebral comedy surely served him well in connecting with many of the Cubans he talked with over the course of four days. It surely allowed him to give his American viewers a new perspective about Cuban culture, from its unique dances to its food, that hasn’t been directly seen by most in decades.

Understanding Cuban culture, not only its politics and government, is vital to understanding how a potential normalization of U.S. relations can occur. Conan told the screening audience that most Cubans he spoke with favored better relations with America and have for a while now. They’ve never known if that was reciprocated. Conan said that when he mentioned a majority of Americans, according to several polls, favor normalized relations, he saw a sense of relief on their faces.

Freer trade can mean an economy that better benefits the downtrodden Cuban people, who have suffered on the whole since Fidel Castro’s 1959 communist revolution.

Any significant changes to the nations’ economic relations will take years, assuming the administration that succeeds Obama’s will even want to follow in his footsteps. And while those changes, if they occur, could largely benefit the Cuban people, Conan said he’s concerned about whether a city like Havana could preserve its historic character.

His concern came in response to a question I asked during an audience Q&A session following the episode screening about what struck him most about Havana.

It took him a couple days to notice it, but Havana lacked something most major American and European cities — at least the gentrified ones — all have: signage. There were no bright LED lights on a storefront for The Gap. There was just beautiful art deco architecture. Even though much of it is in a state of decay, Conan said the lack of signage added a great sense of character to the city that could only have happened in an isolated island state.

While his primary goal was to generate laughs, Conan, the first American late-night host to visit Cuba since 1959, raised some serious points about an issue that’s sure to be close to the center of American foreign policy over the next several years. How can the U.S. work with an adversarial Castro regime to ensure freer trade means better economic outcomes for the Cuban people? How can regular Americans and regular Cubans, not the political leaders of either group, learn to know each other again after decades apart? What can be done to preserve Cuba’s architectural and historical character in the face of potential economic growth and gentrification?

These are important questions for the U.S. to answer in the coming months and years. In the face of a largely failed and outdated embargo policy, it seems appropriate that they are currently being raised most loudly by a comedian on basic cable.


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