Conan O’Brien is disappointed, maybe, with friendly late-night rival Jon Stewart. O’Brien and producer Jeff Ross made a pit stop Wednesday afternoon at Trattoria Dell’Arte in Manhattan between appearances on Howard Stern and The Daily Show With Jon Stewart to pitch Conan’s upcoming special about his adventures in Havana.
“If I can still get giddy about something, that’s miraculous to me.”
But he also had some funny thoughts about the toll a long stretch in the same business can take. “There’s wear-and-tear doing this for a long time,” he told a small group of journalists summoned to hear about the upcoming special (next Wednesday, March 4, at 11 PM on TBS). “If I can still get giddy about something, that’s miraculous to me. The fight now is to keep it interesting. I think there’s going to be a day when I wake up and I think, I just can’t think of another thing that I could possibly do with this form—and then I’ll do five more years.
“I think Jon’s got it all wrong,” he continued. “What I want to tell him is, ‘What if farmers had your attitude? I want to get out on top. This was a good crop, I’m gonna…’ No, no, no we need the food! What if an eye surgeon said, ‘I think I’ve done my best work, I’m out…’ No—these kids can’t see…”
For O’Brien, the four days in Havana was clearly a way to stay fresh. In 1959 Jack Paar had taken the Tonight Show to Cuba and interviewed Fidel Castro, in the brief period between the revolution and the embargo. As soon as the Obama Administration announced the relaxation of rules to allow American easier passage to Cuba, he told Ross, “We’ve gotta go. We’ve gotta go right away because we don’t know what’s gonna happen, we just gotta go.” Team Coco comprised 10 staff members including the host and producer, for the trip over President’s Day weekend.
“We only had four days in Havana,” O’Brien said. “I felt very strongly that I did not want this to be a snarky-American-comedy take, I don’t want this to be political. I want to go as a comedian who’s making fun of himself, and I want to try to make the Cuban people laugh. And in that regard I think we were successful. Everywhere we went people were really open to meeting us, and when I would do stuff with them, improvise with them, they were really funny and really quick.”
One of his objectives was to dispel some of the clichés about a Havana frozen in time. “It’s very easy for us to come in and say ‘These old ’50s cars and the crumbling,’ like a hipster, ‘Isn’t this so cool, let’s leave it the way it is.’ Now you’re being a very condescending paternalistic. When it was suggested he’d done just that by promoting the special with a photo of himself in an ice-cream suit and fedora appendages to an Eisenhower-era land yacht, he riposted, “Right, but that’s just because I look good.”
Over the course of the trip, Conan takes a lesson in Spanish slang, tries to learn salsa, gig with musicians, and even do some stand-up, with varying, if limited, success. The visit that most impressed him, he said, was to a cigar factory. “They let me into a cigar factory where they hand-make cigars, it’s 400 people in a room and they make them by hand and they’re works of art,” he recounted. “It takes nine months of study before they even let you in the factory.” Possibly this is true of cigar factories in the Dominican Republic, Salvador and other cigar-making centers in the region, though admittedly none with the cachet of a Cuban hand-rolled.
“In Cuba, pornography is shooting what they’re up to with their significant other on their cell phone — and handing it to somebody.”
“One thing that was a constant,” O’Brien said of the people he and his crew encountered. “They’re very interested in ‘What do Americans think of us?’ I did not get into the Castro regime and how people feel about the last 50 years. I said America’s a very divided country, we disagree on everything,” but that a poll had shown most Americans in favor of ending the embargo. “They were happy to hear that, they want things to change,” he reported.
Two things glaring in their absence: billboards, and the Internet. “I was talking to somebody about pornography, because that’s the topic I always go to first,” he said. “In Cuba, pornography is shooting what they’re up to with their significant other on their cell phone, putting it on a memory stick — and handing it to somebody.”
Low-key and engaged, O’Brien said he’d been genuinely moved by the trip, both as a new way of working and as a chance to perform for an audience unfamiliar with his his comedy. “Stuff like this re-energizes me. I still love the form,” he said, “but in a world where there’s more and more and more and more shows, there’s more of an impetus to keep changing, do something radically different from what I was able to do 10 years ago.”
Then again, I guess it’s energizing when the old way works, too. “People think comedy’s all about somebody telling great jokes,” he said. “OK, well that’s part of the job, but I believe that two-thirds of it — and [it’s true of] the people who did it the best, whether it’s Jack Benny or Johnny Carson — are the laughs from reacting. So if you’re playing these video games” — which he did on a recent segment featuring Super Bowl rivals Marshawn Lynch and Rob Gronkowski — “and which are horrific, and you’re playing them with Marshawn and Gronk, the biggest laughs in that piece are us honestly reacting to someone’s heart being pulled out through their anus, we’re like Oppenheimer watching The Bomb go off.
“I’ve only, for 22 years, been aggressively pursuing, ‘What’s funny here?,” he said, returning to the subject at hand. “This was a different agenda. Our marching orders for the B-roll was, ‘Get as much as you can of this beautiful city.’ Because it’s going to change and it’s probably going to change quickly.”