“Jon, your quiz does not frighten me,” O’Brien bantered as Stewart — a surprise for the audience — sauntered onstage.
“Perhaps it’s because… you wrote it,” Stewart responded, before launching into a series of questions on city trivia, all setting up O’Brien for some pretty great punchlines. Between discussing the population of Manhattan (1.6 million, but “I just want to make it very clear. No one has any idea how many people are in Manhattan. It’s a made-up thing”) to ripping on the Mets (“Where in New York City is the ball dropped every year?” “Citi Field”), the two covered quite a bit of ground.
At one point, Stewart had to pass of the cue card to Conan’s sidekick Andy Richter, seeming overcome with emotion. “Name the very famous New York resident who won the 2016 presidential election,” Richter finally asked.
Conan’s response: “Hillary Clinton.” That got a big round of applause.
They also riffed on some New-York-specific dilemmas and experiences, from defining Yiddish slang to bemoaning the competitive nature of early childhood education.
“What’s the best way to get a child into a Manhattan preschool?” Stewart asked at one point.
“Has the child been born? It’s already too late,” O’Brien deadpanned.
For the full (unofficial) New York City Citizenship Test, watch the segment above.