Knocked Up's Judd Apatow: How to Turn 40 Year-Old Virgins and Pregnant Ladies into Comedic Gold

Apatow grew up in the upper-middle-class town of Syosset, New York, on Long Island's North Shore. (In his stand-up routine, he mocked the comfort of those surroundings via imagined letters to a Sally Struthers-sponsored Third World kid: "Dear Miguel, how are things in the village? Is the drought over yet? Today my mom made me clean the pool. I hate her!") He was the kind of kid who was picked last in gym class -- "sometimes after girls or after people with broken arms," he says, sitting in an ergonomic chair at his desk after arriving at his Santa Monica offices. "It was depressing to be told you sucked at something every day for years and years, and you could never seem to dig your way out of it. Nothing was more important. It was what made girls show interest in you, it related to who your friends were. It was a daily public humiliation. It was brutal."

By the time he was ten, he had found his salvation -- and life's work -- in comedy. "I wanted to be a stand-up comedian, and I was really serious about it," he says. "The first comedy I liked was the Marx Brothers. I lost my mind about them. I think on some level I was attracted to people telling authority figures to fuck off." After the Marx Brothers, Apatow got into Bill Cosby, George Carlin and Steve Martin, who became an obsession. Before his family had a VCR, he'd use a cassette recorder to tape the audio from Saturday Night Live.

A career in show business seemed attainable: Apatow's grandfather, the late Bob Shad, had a distinguished career in the music industry, founding two small labels and producing albums by Lightnin' Hopkins, Janis Joplin, Ted Nugent and many others. Apatow's dad worked at one of his father-in-law's many labels for a while, and then got into real estate; his mom and dad also owned a Long Island restaurant. Judd's parents separated during the summer between his eighth and ninth grades. "Everyone's parents got divorced on Long Island," Apatow says. But he acknowledges that he works with the same writers and actors over and over partly because he doesn't want to see his on-set families break up.

When he was a junior at Syosset High School, Apatow started his own comedy-themed show at the school's radio station, and he managed to set up a series of interviews with famous comedians, including Jerry Seinfeld, Jay Leno and Garry Shandling -- almost fifty in all. "I think most of them were probably irritated that this child with this eight-foot tape recorder had shown up," Apatow says. He breaks into a vicious imitation of his teenage self, stammeringly interviewing Leno in a high-pitched, Joey Buttafuoco-accented voice: "So do you think when you, maybe, started, in a way, did you think you would be, like, funny? Kind of, maybe, do you think?"

In reality, Apatow -- who still has a trace of that Long Island accent in his rapid speech -- knew just what he was doing. "He gravitated toward showbiz," says retired Syosset teacher Jack DeMasi, who was Apatow's adviser at the radio station. "I've seen a thousand kids do that, and they become accountants. But it was clear from the way he was conducting his interviews that he was learning the business, he was learning what he needed to know to be successful."

Apatow went on to attend USC film school, though he dropped out after a year or so. DeMasi remembers that his application included a story about a "nebbishy guy" whose one moment of glory was starting the Wave at baseball games. "That identification with those kind of characters has fueled where he's gone with his comedy since then," DeMasi says. "There was always that sense of pathos."

Hanging on the wall by Apatow's desk are several pictures of his wife, actress Leslie Mann, who is tall, blond and gorgeous (she plays the drunk who throws up on Carell's face in Virgin). There are also photos of his two daughters (including one shot with Gwen Stefani), a picture of him and Carell with Dan Rather -- and a portrait of the late Warren Zevon, wearing shades and laughing during the sessions for his final album. Apatow is a huge fan, and he got to meet Zevon once in the Nineties, trying to get him to score a movie that was never made. During the meeting for the project -- which was supposed to star Owen Wilson and Rip Torn as Alcoholics Anonymous members -- Apatow casually mentioned that he was waiting for the studio's feedback. Zevon looked at him and asked, "What do you care? Why would you change anything for the studio?"

Apatow was taken aback: "It hit me -- 'Oh, he's an artist! He doesn't give a shit what anyone says.'" Since then -- for better or worse -- he's tried to follow that example.

>>This is an excerpt from the latest issue of Rolling Stone, on stands until June 15th.