In the fall of 1983, Judd Apatow made his way down to a musty room in the basement of Syosset High School and stumbled upon his secret weapon—he just didn’t know it yet.

Apatow was 15 years old, deep into an infatuation with comedy, but had nowhere to channel it. Boyhood on Long Island was something like a John Hughes movie: idyllic on the outside and tormented on the inside. “A lot of what formed some aspects of my personality was that there was an enormous amount of sports happening and I wasn’t good—I would always choke and panic,” Apatow told me recently.

This happened, he emphasized, all the time: in gym class, at pickup games during lunch, after school. “Imagine not being very good,” he said, “and having to be picked close to last multiple times a day,” and then being given a posit

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