Nobody likes making a fool of himself more than Conan O’Brien – he repeatedly proves that fact on his TBS late-night talk show. And Wednesday’s special episode was no exception, as Conan became the first late-night host to visit Cuba since the U.S. embargo started in 1962. ¶ Good idea? Terrible idea? Leading up to the episode, Conan gave multiple interviews where he emphasized the same thing: The idea for the episode (sparked in December when President Barack Obama announced the goal to normalize relations between the United States and Cuba) was that the people of Cuba would be laughing at Conan, not the other way around. ¶ “I like the joke to be on me,” Conan told Southern California Public Radio. “I wanted it to be really funny and have belly laughs in it, but I also wanted it to be sweet. We very much went in with a feeling of, we’re going into another culture and we want to respect that culture, and all I want to do was try and make people laugh.
I didn’t want to do comedy where I’m making fun of something in their society; that’s just rude.”
The 80-minute episode was very similar in tone to Conan’s many other goofy remote segments around the world, from Canada to Finland. As tradition, he played the jester as everyone stared in polite horror and/or made fun of him. Here were the five most “Conan” moments of the episode:
• Conan interacts with non-humans.
Though Conan joked with lots of people around Havana, at the top of the episode, Conan gave a voiceover in which he briefed viewers about the rocky history between Cuba and the U.S. But because relations between the two countries are starting to thaw, it was the perfect time to check it out.
“I kept the purpose of my visit simple,” Conan said, acknowledging the country’s complicated social and political problems. “To meet people and try to make friends.”
Typical segue: Tons of dogs all barking at Conan as he tried to walk down the street in Havana. The host didn’t let that stop him. “Yo soy Conan!” he yelled as more canines emerged, none too happy to see him. Walking by a house, he finally got a friendly response from a woman who returned his greeting. “Old women love me here, dogs hate me,” he confirmed.
• Conan is self-deprecating.
While taking some very unproductive Spanish lessons (“How do you say, ‘I am new to Havana and I would like to get my fro-yo on?’”) Conan pulled one of his familiar bits where he lets you know that he’s a celebrity, but not really that big of a deal.
“How do you say ‘I am America’s biggest star?’” he asked the teacher. “And how do I say ‘Don’t check on that, don’t look into it, just trust me?’”
“I am Ryan Gosling!” he roared as the students started laughing. “Yes, I am the most handsome movie star in America! Gaze into my ojos.”
• Conan makes fun of his own company.
Luckily for Conan, TBS’ parent company Turner Broadcasting also owns CNN, which led to a hilarious segment where Conan stood on a roof looking over Havana, pretending to be a journalist narrating the action: A dog started barking. Then it stopped. Then it started again. Etc.
“I’m now realizing Anderson Cooper has a very easy job,” Conan commented as a fake CNN scroll appeared on the bottom of the screen with the chyron “DOG BARKS AGAIN.” This went on for awhile, until he added: “I think what we’ve just proven here is I could fill six hours a night on CNN.”
• Conan makes life difficult for someone just trying to do her job.
One of Conan’s greatest strengths is to annoy people who are very sincere about their work, to the point where they just have to start laughing at him. Gretel the tour guide at the rum museum, for example, was just trying to do her job and teach Conan some rum history – he wasn’t interested. “Another section of not the rum tasting,” he joked as poor Gretel tried to interest him in some fun facts. Eventually, though, they became pals as he got “drunk” at the rum tasting and she sang to him while he was nearly passed out on the bar top. His visit to a cigar factory was similar, as the workers tried not to be horrified at his sad attempt at rolling cigars.
• Conan dances.
And failed miserably every time! Even though he could not get the hang of the rumba, he did his famous string dance.
In the end, he called his trip one of the greatest experiences of his life, and raved about the people he met — just before he started dancing through the streets in a white suit in a Cuban parade.
“I can’t say enough good about the people of Havana and Cuba, and I can’t wait to come back.”