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A few months after he brought his show to Haiti, Conan O’Brien headed to Italy for his latest travel special on Wednesday night, where he attempted to speak Italian, bantered with colleague Jordan Schlanksy and shouted out random Italian words on the streets of Florence.
O’Brien previously explained when announcing the special that he decided to take Schlansky, a Conan associate producer, because he always “acts like he’s from Italy” though he’s from a Polish family on Long Island. (Schlansky also travels annually in Italy.) O’Brien and Schlansky often do comedy sketches on Conan together, where Schlansky often plays a snobbish and detached type to Conan’s emotional and overwrought persona, the two trading roles as straightmen.
Across the show’s airtime, O’Brien and Schlansky took a road trip from Florence to Naples, driving through Chianti wine country, going truffle-hunting in Tuscany, being received by a local mayor in Cortona and Conan appearing on the Italian soap opera Un Posto Al Sole.
When walking in Florence, the pair’s first destination, O’Brien informed Schlansky that he likes to shout out random Italian words on the street because he believes it makes him sound “popular.” Schlansky then argued that Italians might find it insulting for an American to shout out random words or make them up. When Conan shouted “pesto” at a passerby and the person said “pesto” back, he argued that the exchange showed that Italians didn’t find it offensive. Then one lady responded by calling him an “asshole.”
O’Brien also took a drawing class at Florence’s Accademia D’Arte, where he attempted to draw the likeness of a nude model. He started to give the model some characteristics that looked like himself. “I’m called a narcissist in America, you know what that means?” he asked the instructor. “Because I always end up drawing myself.”
Schlansky then subbed in for the nude model, doing poses that O’Brien asked of him including “Naked Man Looking for a Ride” and “Mentally Ill Man Attacks” as another student and the instructor grimaced.
At one point, the pair’s car, a 1962 Fiat, chosen by Schlansky, stalled and so O’Brien pushed it along narrow Italian streets. “What are you gonna do?” he said to onlookers in a fake Italian accent as he nudges the car on. The moment came after O’Brien spent a lot of time complaining about the car’s size and lack of airbags. “But we’ve got a windbag,” he said, pointing at Schlansky.
The pair also went hunting for Tuscan truffles with two hunters, who they eventually suspected hid the truffles ahead of time. “We’ve been scammed,” O’Brien said dramatically to the camera, voicing his suspicions throughout the “hunt.”
During a Tuscan wine tasting, O’Brien drank all of his glass of wine instead of spitting part of it out, and then, when Schlansky protests, he drinks Schlansky’s, too. “Watch this. It’s something I learned in alcoholism school,” he jokes.
The two bickered endlessly during the tasting, comparing each other’s personalities (unfavorably) to certain wines. “I would like to push you into a barrel and seal it,” Conan joked.
In Cortona, Schlansky’s favorite town, they were welcomed by the mayor and Schlansky was given a parking space in his name. He then gave a long, winding speech in Italian to an empty square about what he likes to do in the town before a pair of Italian policemen led him away.
When Schlansky attempted to introduce O’Brien to Italian cappuccinos, he called the process of making it “a dance between man and machine.” O’Brien protests, “He’s making a cup of coffee!” O’Brien later asked the baristas if they could make him a pumpkin spice latte, their disgusted reaction to which the special showed in slow motion.
Conan also continued his travel-special tradition of appearing on a local soap opera, this time as a background extra on Un Posto Al Sole. Schlansky, dressed in a black wig and fake mustache, also appeared in the margins of one shot.
The special ended with O’Brien debuting a Fellini-esque, black-and-white mock trailer for his special with Schlansky called Due Buffoni, or Two Buffoons in English.
Conan in Italy was the late-night host’s ninth international trip in three years, and his first with colleague Schlansky.
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