Nicholas Stoller

One night, nearly two decades ago, Nicholas Stoller, at that time a freshman at Harvard, dragged his mattress out of his room and into the room of his suitemate. Both young men had long-distance high school girlfriends whom they missed terribly, and they'd decided to have a sleepover to bond over their shared state of longing. During the sleepover, the suitemate decided to put on his prom song, “Always” by the English synthpop duo Erasure. The two listened as a ghostly plucking of strings filled the room, accompanied by a faint, mournful moaning, then a pulsing beat and quirky, digital squiggles of synthesizer funk. And soon, a high-pitched male voice, wavering and rising with emotion, swelling at the chorus: Always/I want to be with you/and make believe with you/and live in harmony harmony oh love. The song played, and they both cried.

Stoller laughs as he tells this story. He is now a successful 36-year-old filmmaker in the midst of press rounds and premiere screenings for his latest movie, “The Five-Year Engagement,” which he directed and co-wrote with frequent collaborator Jason Segel. He quickly, flatly sings a couple of lines of the chorus. “It's a terrible song. You should really check it out.” We are sitting in the hotel bar at The Pierre in New York City, a windowless room on the ground floor. The bar is strange, a tiny pocket of old New York class—tiny tiles, brass, dark wood, piano music—that someone tacked purple lights onto in an ill-advised effort to introduce a modern, club-like vibe. The result is almost lewd, slightly depressing, but also funny, and Stoller called attention to it as soon as he entered the room, saying “Wow, this place is so weird, sorry. I feel like we're in Russia or Shanghai or something.”

Stoller's crying freshmen story is significant for a few reasons. For one, it's a small, neat anecdote loaded with messy emotion, (almost) grown men crying during a shared, self-indulgent, sentimental moment gone suddenly too intimate, and the ensuing awkwardness of that—it's a perfect encapsulation of what Stoller finds funny. It also may have been, in retrospect, a pivotal moment in his life. A few years later, face-to-face with Judd Apatow and Paul Feig, who were then interviewing young writers for their show “Undeclared,” Stoller decided to pitch his weepy man-sleepover as a story idea. Apatow laughed hard, and Stoller believes the pitch is what got him hired.

There is a boyish quality about Nick Stoller that has partly to do with the combination of his young-looking face and his no-longer-crisp sport coat, but is also perhaps a byproduct of his profession: constantly collaborating with other funny (mostly male) people to invent, write down and or make movies about funny situations, finding humor in himself, in the world around him, the people around him. He is amiable and laughs easily and often. A bit of a fast talker, one gets the sense that his gears turn a few speeds quicker than most other people's. He is a self-described people-pleaser, always working hard under a self-imposed pressure. He imagines that the people who know him best would describe him as “nice.” He doesn't elaborate much beyond that; the topic makes him slightly uneasy. “I feel like I'm about to sound self-congratulatory,” he says, adding that he doesn’t like to talk about himself, even when he wants to. However, he does enjoy doing press for his movies, he says, somewhat jokingly, because he can talk about himself without feeling rude.