A few months after he brought his show to Haiti, Conan O’Brien headed to Italy for his latest special abroad on Wednesday, 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. 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, O’Brien informed Schlansky that he likes to shout out random Italian words on the street because he believes it makes him sound “popular.”
O’Brien also took a drawing class at Florence’s Accademia D’Arte, where he attempted to draw the likeness of a nude model. 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 nudged the car on.
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 protested, he drank Schlansky’s, too. “Watch this. It’s something I learned in alcoholism school,” he joked.
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.
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 protested, “He’s making a cup of coffee!” later asking the baristas if they could make him a pumpkin spice latte (their disgusted reactions spoke for themselves).
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.