Conan O’Brien has sat behind a desk and hosted a talk show for more than twenty years, but his funniest moments continue to come when he leaves the set and puts his gangly six-foot-four-inch frame and rooster head out among the people. The recurring joke—whether O’Brien is visiting Houston to demand that “Late Night” get a better time slot or travelling to Ireland, Germany, or Australia—is seeing his aggressive self-regard butt up against the indifference of the men and women he meets on the street.

On Wednesday night, on his TBS show, O’Brien aired a special that was assembled from a recent four-day trip he made to Havana, in what has been marketed during a press tour this week as the first time an American late-night host has shot an episode in Cuba since the U.S. embargo began, in 1962. Fittingly, no one there seemed to know who Conan was, or what to make of him.

O’Brien travelled to Cuba in February, on a mostly low-profile trip taken with his producer, his head writer, and a camera crew. He was delayed for a few hours upon arrival at the airport near Havana, he told the Los Angeles Times, but was subsequently allowed to travel and film freely for the next four days. The goal was simple: “To meet the people, and try and make friends,” as O’Brien says in the special’s opening voiceover.

He has, let’s say, mixed success. During a Spanish-language class, he becomes upset when the teacher impugns his eighth-grade-level pronunciation; on a tour of the Havana Club rum distillery, he badgers the young guide to move things along to the tasting session at the bar; he commandeers a salsa band, singing gibberish. “Old women love me here, dogs hate me,” he says. He badgers people on the street; tries to convince a bunch of children that he is, in fact, a talk-show host in the United States (“That’s a lie,” a little girl replies); and struts around in a white-linen suit and cream-colored panama hat. Nobody does the American idiot abroad better, and for that reason alone O’Brien is a fair pick for cultural ambassador to the people of Cuba.

The special is not revelatory in its depiction of the country. O’Brien does things any tourist might do: he attempts to dance, rolls cigars, drinks mojitos, admires all the midcentury American cars, takes a frightening cab ride in an old Lada with a faulty passenger door. More notable is the way he mixes wide-eyed enthusiasm with sombre, ambivalent notes. “Change is never simple or easy to predict,” he says at one point. “Will the sudden influx of American money make things better for the average Cuban? Definitely. Maybe. I’m not sure.” Then he imagines the crumbling buildings around him replaced by a Chase branch and four Foot Lockers. Would Jimmy Fallon take a break from declaring how awesome everything is to make such a point? Probably not.

The Cuba trip was a far cry from what had previously been O’Brien’s most significant venture into geopolitics. In 2005, after he was made aware of his striking resemblance to then Finnish President Tarja Halonen, O’Brien filmed a campaign commercial supporting her for reëlection, and the next year made a triumphant trip to Finland. He was greeted by huge cheering crowds and his visit was widely covered in the local media. This coincided with what was probably the height of his cultural influence back home. Having been named in 2004 the heir to “The Tonight Show,” scheduled to take over in 2009, O’Brien existed in a cultural limbo of good feeling, admired for all he had already done while also touted as the future of late night.

Nearly a decade later, there were no cheering crowds in Havana. O’Brien has returned to his natural state: the outsider eager but unable to please, a self-pitying small-timer, ingratiating and infuriating. Hosting “The Tonight Show” may well have been his dream, but it is on TBS, where he is left to his own weird devices and entertaining a distilled audience of hard-core fans, that Conan can most fully embrace the persona that made people love him in the first place. Near the end of the special, as he enjoys an elaborate meal at a local paladar, he turns to the camera and says, with a dour look, “This food is so good, I’m starting to forget that I’m alone.” As always, O’Brien is funniest when he’s not fitting in.