Walking Down Memory Lane With Judd Apatow

Filmmaker reminisces about growing up in Syosset

Judd Apatow might currently be one of Hollywood’s most successful producers and directors, thanks to his work on projects ranging from The 40-Year-Old Virgin and Trainwreck to Freaks & Geeks and Girls, but the seeds for his creative prosperity were planted in his Syosset hometown. He is currently making the rounds promoting The Zen Diaries of Garry Shandling, the two-part, four-and-a-half-hour documentary that recently debuted on HBO and is a thorough look at the life of his late mentor. In a way, this film not only serves as a cathartic exercise for the Long Island filmmaker, but it brings Apatow full circle to the first time he crossed paths with Shandling as a teen attending Syosset High School.

“I had been friends with Garry since I was in my early 20s and even interviewed him when I was 16 years old for my high school radio station on Long Island, WKWZ Radio in Syosset High School, 88.5 by the way,” he proudly said. “I was doing interviews for my high school radio station. These were the days that were pre-Internet, and in my own way, I think I was podcasting before there was podcasting. I was very interested in long-form interviews and I hunted down people like Jerry Seinfeld and Howard Stern and I was able to get an interview with Garry right after he hosted The Tonight Show for the first time, which was a big deal. Nobody was allowed to do that. So I did this interview over the phone while he was in Las Vegas and it’s funny that in the documentary the interview that talks about that time is the one that I did with him when I was just a child.”

Syosset High School (Photo courtesy of Syosset Reach)

Growing up as the product of a divorced family in Syosset in the late 1970s and 1980s proved to be a safe haven for Apatow and his friends. Like so many others that grew up in that time, it was very much a latchkey kind of existence.

“I grew up in Syosset and Woodbury and I have very fond memories of living there. Now that I’m an adult and am raising two daughters, I realize what a great community that was and how great Syosset High School was and how safe I felt,” he said. “Me and my friends would just wander around. After school, we’d just hop on our bikes until dinnertime. We had so much fun and felt like everything was going to be all right. People don’t live that way as often anymore. We’re all so scared and hiding in our houses, afraid to let our children wander off. Most of our parents were divorced, so we would just escape and go to On Parade Diner at midnight when we were 11 years old. It really was idyllic in a lot of ways as a community.”

But it would be at school where Apatow was able to indulge his obsession with the entertainment world and get validation for his dreams, thanks to the encouragement of some key adults and a radio show he hosted on the 125-watt WKWZ called Comedy Club.

Judd Apatow’s mentor, Garry Shandling, gave the Syosset native his first break. (Photo by Bonnie Schiffman/Courtesy of HBO)

“I look at Syosset High School as the reason why I succeeded. There was a man named Jack DeMasi, who retired a little while back who ran the high school radio station and taught film and TV classes there. He was the guy who treated me like a young adult. So when I asked if I could do a show where I interviewed comedians, he encouraged me and I became the station manager. That experience turned me into a leader and it turned me into a hustler,” Apatow explained. “I worked my butt off to take the big chances to try and make my dream come true. I learned how to do that at Syosset High School.”

Just as crucial was an experience Apatow had with a writing assignment that not only gave him a huge confidence boost, but helped shape his perspective when it came to paying it forward later in life.

“I also had a teacher there, Mrs. Farber, who taught English and asked us to write our autobiographies. I didn’t want to be truthful, probably because my parents got divorced. I didn’t know what to say, so I made up that I was a CIA agent who was undercover at the school and that I was having affairs with all the teachers. It was very imaginative and funny, and instead of getting mad at me, she said, ‘You know, you’re really funny. You could have a career like Woody Allen,’” Apatow recalled. “No adult had ever said that to me. I’d only gotten punished for writing things like that. I never forgot it and I really believed her. It gave me confidence for some odd reason, because she was a smart, cool woman and I’ve always been appreciative of that. That’s part of why I’ve tried to mentor people—because of people like Mrs. Farber, Jack DeMasi and Garry Shandling. I understand how important kind words could be.”

Read our full feature on Judd Apatow and The Zen Diaries of Garry Shandling and check out Apatow’s favorite projects that he worked on with Shandling.

Apatow’s Fave Garry Shandling Projects

The Zen Diaries Of Garry Shandling

Dave Gil de Rubio
In addition to being editor of theNassau Observer, Dave Gil de Rubio is a regular contributor to Long Island Weekly, specializing in music and sports features. He has won several awards for writing from Press Club of Long Island (PCLI), New York Press Association (NYPA) and Fair Media Council (FMC).

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