Conan Goes to Italy

Conan O’Brien Doubles Down on the Value of Pure Silliness

While the rest of the late-night world wades through the topical apocalypse, the veteran host continues to embrace his status as national clown. In his latest travel special, O’Brien teams up with his longtime associate producer Jordan Schlansky for an anarchic six-day tour of Tuscany.
Conan O'Brien
By Yonatan Sindel/Flash90/Redux.

At a moment when American political news offers an embarrassment of riches for late-night talk-show hosts, Conan O’Brien has been busy offering viewers a different kind of relief. Prioritizing vaudevillian silliness over substance has always been O’Brien’s stock and trade. Yet given the current political climate, one would think he’d be tempted to leverage his American-history degree from Harvard and comment deeper on current events on a nightly basis. But he says his passion for American democracy has never collided with his taste in comedy.

“I love that this show is just a confection. It’s just pure silliness,” he says of his latest international episode, Conan Without Borders: Italy, which premieres Wednesday at 10:00 p.m. on TBS.

“When I was 16 years old I was taking a driving class, and the old guy who was teaching me said, ‘if you want to drive through a narrow space, just look at the space, don’t look on either side,” he says. “Don’t pay too much attention to what’s around you because then you’ll consciously drive into it.’ I always thought that way about comedy. When somebody does something really good, I’m aware of it, but I’m not actively looking at other people, because that’s not where I get my inspiration.”

“There’s part of me that is delighted that everyone is talking about the raid on Trump’s lawyer, and what was seized, and what’s in those papers. And what’s Conan up to? He’s in Italy with one of his producers, torturing him,” he says.

That hasn’t stopped some viewers from accusing him of having an agenda, most recently when he travelled to Haiti in the wake of Donald Trump’s comments about “shithole countries.” But he says the motivation to make a point ends with the choice of destination.

“Clearly going to Haiti was in response to something that happened, but most of what we tried to do there was be funny. And the same thing in Mexico, and the same thing in Cuba. My favorite moments from those shows aren’t overtly political. They’re just human,” he says.

Though speaking about his travel specials, O’Brien could just as well have been talking about the general approach he’s taken to his nightly show for the better part of two and a half decades. This month marks the 25th anniversary of NBC’s announcement that a young, relatively unknown veteran of the Simpsons and Saturday Night Live writing staffs would be the new host of Late Night, replacing David Letterman. He was a 29-year-old kid with a nervous high-pitched laugh, who, when he appeared on Jay Leno’s Tonight Show stage the night he signed the deal, looked like he hadn’t fully realized what he’d gotten himself into. Today, he’s the longest-serving nightly talk-show host on television.

“It feels like a lifetime, and in a good way. So many different intense things have happened in 25 years. There have been so many high highs, low lows,” he says. Among the intense lows: being given and subsequently giving up the hosting duties of The Tonight Show in 2010. The high-profile behind-the-scenes drama that has plagued the genre for decades may make for a good media narrative, but the still oft-cited “late-night wars” don’t reflect O’Brien’s daily reality.

“I’ve been hearing it so long that it’s ephemeral,” he says. “What about the work? Did you like it? Did you laugh? Did you not laugh? The supposed ‘war’ between Leno and Letterman, it didn’t matter at the end of the day. You either liked one or you liked the other one. They had something funny one night or not. The rest is just all going to be forgotten.”

Refining how he delivers his comedy is still a constant evolution for O’Brien, and his travel specials, which began with Cuba in 2015 and have included trips to Korea and Israel, have lately played a large role in that process.

“As much as I love the job I have in the studio, I really am enamored with the job I have outside the studio. That’s been re-energizing. I think if it was 25 years and I was still doing exactly what I was doing in ’93, you would be talking to an unhappy person,” he says. In his latest travel special, O’Brien spends six days exploring Italy alongside his associate producer (and according to O’Brien, “fake Italian”) Jordan Schlansky.

Viewers first became fascinated with Schlansky’s quirks after O’Brien filmed a 2008 Late Night segment in his office. The two have been mutual comedic foils ever since. In Italy, O’Brien relentlessly bullies Schlansky for his stoic pontifications, embarrasses him in a language class, and makes liberal use of a fart machine during what’s supposed to be a peaceful drive through Tuscany.

“I’ve been in comedy a long time, and I’ve never had this chemistry with anybody,” O’Brien says, noting that fans ask about Schlansky everywhere he goes.

Their dynamic is a departure from O’Brien’s solo travel specials. In those, his interactions with regular people are rooted in empathy, and he makes himself the victim by struggling (and invariably failing) to learn local customs. The iteration of O’Brien’s persona that has him being the joke, instead of just delivering a joke, is a style not often seen on mainstream television: clown. The word has plenty of baggage, particularly in America, but O’Brien is happy to carry it.

“It is an accurate label,” he says. “I’m a very physical comedian, and I take pride in that. I like to use my face in lots of different ways, and take strong emotional stances for comedic effect, whether it’s I’m enraged or I’m crushed and humiliated.”

The travel specials will continue being a large part of his evolution. He won’t predict exactly what iterations his comedy will take in the future (his current contract with TBS goes through 2022), but it’s fair to expect he’ll eventually step away from some pillars of the traditional talk-show format.

“How much of it is rote? How much of it are we doing just because that’s the way it’s always been done? And does it have to be done that way? Those are daily discussions that we have here. There’s not a day that goes by that I don’t say ‘wait a minute, why am I just doing a desk piece that could have been done in 1952? Why don’t you just not do that anymore?’ We have discussions about it, and sometimes arguments about it, and then things gradually change,” he says.

For now, whether he’s behind his desk in Burbank, or crammed into the passenger seat of a vintage Fiat in Italy, he keeps his method simple.

“Try and make a good, funny, laugh-out-loud moment, and the rest will take care of itself.”