Conan O’Brien on playing ‘American idiot abroad’ in visit to Cuba [Exclusive Video]

“I take that as a compliment. The ‘American idiot abroad’ is an invention Mark Twain was doing in the 19th century. The American being out-of-place and out-of-sorts and being the butt of the joke is part of a long, rich American tradition of humor,” says Conan O’Brien when talking to us about the special “Conan” episode filmed on location in Cuba earlier this year (watch our full conversation below). He adds, “When you send someone like me there, who is not afraid to look silly and the joke to be on me, it’s actually a sweet message. It almost feels like a form of diplomacy.”

Watch dozens of video chats with 2015 Emmy contenders

O’Brien earned raves for the episode which aired in early March during his regular TBS time slot. He and his producers got the idea after the U.S. government opened up restrictions on visiting Cuba. He reveals that after President Barack Obama made the announcement, “we decided let’s make this happen quickly. Let’s do it, because I think people are going to be broadcasting from Cuba left and right. Once ‘The View’ is in Cuba, we know the fun is over.”

He adds that it was a real “guerrilla” effort bringing just a handful of people and that “we realized no one had done it since Jack Paar had taken ‘The Tonight Show’ to Cuba in 1960. Wouldn’t it be fantastic if instead of interviewing celebrities, I jumped into part of the culture, met the people, and really tried to make friends?”

The four days of shooting led to segments where O’Brien learned to dance, rolled cigars, took a Spanish-language class, drank lots of Havana Club rum, commented on the old buildings, took a crazy cab ride, and showed off his white-linen suit and panama hat.

With David Letterman‘s recent retirement, O’Brien is now the longest-serving late night host on the air. Having replaced Letterman on NBC’s “Late Night” in 1993, he has now worked 22 years on the late shift. He is a three-time Emmy Award winner: as a writer for “Saturday Night Live” (1989), a writer for his own show (2007), and for interactive programming with TeamCoco (2012). The Cuba visit will be the episode submission to Emmy judges this summer if “Conan” is nominated again.

Related: What am I going to do now that David Letterman is retiring?

Make your predictions and you could win a place of honor on our leaderboard, a starring role in next year’s Top 24 Users (the two dozen folks who do the best predicting this year’s Emmys line-up), and one of three contest prizes: $500 for first place, $300 for second place, and $200 for third place. Prizes will be bestowed as gift certificates to be redeemed at Amazon. See our contest rules for more info.

Average Gold Derby users just like YOU often turn out to be our smartest prognosticators, so it’s important that you give us your predictions. Your picks influence our User racetrack odds, which also factor into our official combined odds.

The Top 24 Users did the best at predicting last year’s Emmy nominations (78.55%) when competing against Gold Derby’s Editors (77.68%), all Users (74.78%) and the Experts (74.64%). Which group will be victorious this year?

Register/log in to your account (or create an account with one click using Facebook, Twitter, or Google) so you can compete to predict the Emmy Awards, “Game of Thrones,” reality shows and more.

More News from GoldDerby