O’Brien (along with his crew) did, in fact, make history by being the first US late-night show to film in Cuba since 1962. That means for fifty-three years the good people of Cuba weren’t able to experience the strange rituals of corny American monologues, comedic sidekicks and bandleaders, and celebrities awkwardly sitting on couches with pre-scripted anecdotes. Who better to re-introduce them to our silly ways than an extremely tall (and pale) man with fiery red hair?
In this slightly longer, special episode of Conan, O’Brien immersed him in Cuban culture—as seamlessly as he could as a tourist with a camera crew in tow—learning everything from how to properly roll cigars and do the rumba, to brushing up on his self-proclaimed “eighth grade Spanish” and rum drinking. While it was a given that hilarity would ensue within each of these wacky fish-out-of-water situations for the American viewer, it was exciting to see people laugh at the talk show host’s antics, regardless of having never seen or heard of him before. We’re sure it was a comforting sound to the twenty-two year late-night veteran who has been through the ringer before.
Here we’ve compiled some of the best moments of Conan In Cuba. Watch the entire episode below.
Conan’s informative intro
It used to be easy for Americans to visit Cuba. In the 1940s and ’50s it was the Las Vegas of the Caribbean, but in 1959, Fidel Castro led a revolution to topple the dictatorship, which led to an economic block that lasted fifty-three years. Then in December of last year, President Obama announced he wanted to normalize relations with Cuba, establish formal diplomatic ties, and pending congressional approval, lift the embargo. Cuba is a country with many complicated social and political problems, so this process won’t be easy, which is why I kept the purpose of my visit simple, to meet the people and try to make friends.
Conan brushes up on his Spanish
How would you say “I am America’s biggest star”? …and how do I say, ‘Don’t check on that. Just trust me.’?”
Conan leads a salsa band
What a way to love you, what a way / I am Nutella, I am Nutella / Men have libraries / Happy Birthday, Happy Birthday / I am beer, and drunk / I when and love with Carlos / I Diana with one hand and two hands / The cat and the dog / I go call the people and it’s the tip for the cars / Hamburger milk / Go away chair / Jar, clothes
Conan partakes in a rum tasting
Your rum is the best rum I ever had in my life! Can I stay here until the rum comes to the United States? Do you have a place I can stay?
Conan takes in the views
There are some attractive women here on the corner having a drink and something to eat, but, of course, they don’t know me. For me to even try to speak to them probably would be rude, so I will just talk about them while standing three feet away. With a camera. Which isn’t rude, it’s creepy.
Conan shows off his dance skills
I have one concern. I’m worried she, my partner, will fall in love with me.
Conan addresses a cigar factory
Hello, my name is Conan O’Brien. I am a giant star in the United States. I know that you are very excited to see me, and you’d like to meet me, and possibly hug me—especially the ladies and some of the men—but you should remain seated.
Conan enjoys the local cuisine
This food is so good, I’m starting to forget that I’m alone.
Conan tests a new market for his show
Young girl to Conan: That’s a lie.