The 2022 book Sicker In The Head includes conversations with Cameron Crowe, David Letterman, John Mulaney, Kevin Hart, Margaret Cho, Whoopi Goldberg, and Will Ferrell, among others. By simply asking “how are you doing?” during the pandemic, Apatow felt he could grow as a creative and a person based on many of the responses from the interviews.

One particularly unique interview is between Apatow and Crowe, where both had unique upbringings around the icons they most admired. Apatow interviewed comedians for the school newspaper (stories which became the book Sick in the Head) and Crowe interviewed bands for Rolling Stone (stories which became the movie Almost Famous).

For these types of interviews, he reads a handful of Q&As or listens to podcasts to prepare. He felt a deep connection with David Letterman, who revealed he appeared to be having fun but was actually a ball of nerves. Apatow often feels the same way on set.

Judd Apatow. Photo by Mark Seliger

“When I was in film school, they were always talking about structure. I didn’t want to have any rules. I hated that they were trying to box me in. I even took a class with Syd Field where he basically read his book to us, but then I started writing spec scripts and I realized they were all correct,” he joked. “

Syd Field told him, “I know you don’t think you’re going to do this structure, but whatever you’re doing, you have to have this structure. The inciting event. The conclusion. I still use all of that today. I use the Syd Field paradigm.”

Audience Validation

Similar to stand-up, Apatow said you do feel the validation when an audience watches your movie, in terms of using the three-act structure or Chris Vogler’s examination of The Hero’s Journey. “It’s one of the best books you can buy on storytelling,” he said of Vogler’s book.

Based on Apatow’s response, he writes his own version of the story first, then re-examines The Writer’s Journey to see “which story” he’s doing or to help with missing plot points. “Even with weird things like You Don’t Mess with the Zohan, it is ironically a reluctant hero’s journey.”

Using these methods helps Apatow take risks in his career. “I think they’re all risks because in comedy, they’re all risks. You just never know if it’s going to work. Like, would someone watch a movie about a 40-Year-Old Virgin? Is that the worst idea you’ve ever heard in your life?” he joked. “Steve [Carell] and I said, well, let’s make it totally credible. He’s a normal sweet guy and [sex] just got past him.”

Trish (Catherine Keener) & Andy (Steve Carell) in 40-Year Old Virgin

He continued, “Maybe it’s about relationships. He has to figure out how to have a relationship and that’s way more complicated than just sex. All of his friends are trying to have sex, but he finds love,” he said, adding that Garry Shandling helped with the overall theme.

Then, there are shifts within films in terms of risk. The King of Staten Island was meant to be more grounded where The Bubble was meant to be like a Mel Brooks-like satire about the pandemic. “Can you be funny about it? Can you talk about isolation and the weird feelings we have when we’re forced to be in isolation?”

In terms of advice for screenwriters, Apatow said “you can usually tell when someone has a voice.” He continued, “If someone is writing with some specificity and you feel the soul of someone in the writing, it’s clear when someone is generic and when someone is coming across to you.”

“I remember, a long time ago, some producer said you can open up to any page and tell if it’s worth reading and if that person knows what they’re doing. It sounds horrible, but it’s kinda true. I just always tell people to write about something you really care about. You can tell when people are writing to make money, but writing is always better when you’re offering something and giving yourself. You have to go all the way.” This interview has been condensed.

Listen to the full audio version here.