Judd Apatow on Why He Produces Documentaries Like ‘Flipside’: ‘Life Is More Fascinating Than Fiction’

In “Flipside,” documentary filmmaker Chris Wilcha grapples with personal regrets and middle age through the lens of the documentary projects he started but never finished. The 96-minute doc, which premiered last year at the Toronto Intl. Film Festival, looks at those abandoned ideas including one about television writer David Milch and his connection to jazz photographer Herman Leonard; a passion project on the New Jersey record store where Wilcha worked as a teenager and a look at radio host Ira Glass’ attempts to make a musical.

Writer/director Judd Apatow executive produced “Flipside.” Apatow met Wilcha in 2009 when he hired him to make a behind-the-scenes movie about the making of “Funny People.” Wilcha moved his family of four from New York to Los Angeles to work on the project with the idea that he would become a successful documentary filmmaker. But when that career didn’t take off, Wilcha began a lucrative career making commercials. In “Flipside,” the director ponders his expectations and where life and time have led him. The result is a moving meditation on work, family and the sacrifices and satisfaction of trying to live a creative life.

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Oscilloscope Laboratories releases “Flipside” in theaters on Friday.

Variety spoke to Wilcha and Apatow about how the project came about.

Judd, you recently served as an executive producer on Peacock’s “Stormy,” about Stormy Daniels. “Flipside” is a completely different type of docu. What about it appealed to you?

Apatow: Chris and Joe Beshenkovsky, who edited “The Zen Diaries of Gary Shandling” and “George Carlin’s American Dream” for me, sent me a hunk of this project and I loved it. We had a really good time riffing about its possibilities. I was fascinated by the fact that so many of the narrative strings connected in strange ways. I just had a feeling, like they both did, that there was something very magical happening that if fully explored would be very moving.

In the doc, Chris’ mother expresses her dismay with you because you are the reason why her son and grandchildren live 3,000 miles away from her New Jersey home. You didn’t feel pressure to sign on as an executive producer to make it up to her?

Apatow: I didn’t realize how serious she was (about that) until I talked to her. In a way, that’s always my worst fear. When I did “Freaks and Geeks” a lot of the cast moved to America from Canada and didn’t go to college because they got a job on a TV show. I’m always feeling guilty, even when I’m doing something that I think is positive, that in some other way I’ve destroyed lives.

Chris, in the film you explore your disappointment around giving up documentary filmmaking to “sell out”  and make commercials. Looking back, given the doc industry’s dismal landscape, are you happy with the trajectory of your career?

Wilcha: Yes. I mean, the whole thing about this film is there are so many contradictory things that you have to hold in balance to be an adult. I feel immense relief, especially when I see some of my non-fiction peers who don’t have a commercial directing career to fall back on. So, I feel incredibly lucky that I still get directing work and I’m still able to contribute to my healthcare and stuff. But I look back on the last decade, because I was in one of those modes where we had young kids and I was just trying to make a living and hustling to get the next job. This film was an occasion to look back. Look, there is some heartache that I haven’t made more documentaries. I envy those handful of people in the doc space who get the call for the epic biopic, or the one about the band that I love. I’m sort of like, I wish I was in the mix for those films.

In “Flipside” you mention how Errol Morris, at least in the beginning of his career, funded his documentaries by making commercials. Did your commercial work fund this film?

Wilcha: Yes. I would often do a commercial and I would ask the crew if they could come with me for an extra day, and we would use the camera that had been rented for the week to shoot (the doc). So, I was constantly living off the fat of commercials. But there came a point where we had to seek investors. The whole effort of any documentary shooting I’ve done is because of the commercial work. That’s the thing that pays for it. That subsidizes it. I’ve never solely made a living off of documentary filmmaking. And by the way, you said that commericials were Errol’s early (funding) model. He actually directs more commercials than you can even imagine. I lost a job to him last week for an insurance commercial.

Judd, the last two films you directed were docus — “George Carlin’s American Dream” and “Bob and Don: A Love Story.” You have been so successful with your studio narratives, why bother with docs, which oftentimes have tiny budgets compared to fiction films and can’t find a big audience?

Apatow: When I worked with Gary Shandling it was always about how truthful you can get. He always wanted to go as deep as possible and the next step is to just go to documentaries. That’s the logical road. I find people fascinating and a lot of times life is more fascinating than fiction. There is also something less pressurized about it because you are just chipping away to get to the truth. You aren’t up all night trying to beat your joke. I just find it to be more enjoyable and oddly less stressful than making comedy.

In “Flipside” Herman Leonard says something along the lines that creatives want to leave something behind something important that people remember, but it’s never enough. Judd, you have created so many things that people are going to remember. Is it enough?

Apatow: It’s funny because as soon as the last (film) ends, I always truly feel like I’ve never made anything. I have no self-esteem. I have no gas in my tank. It doesn’t make me feel like it’s time to rest. I have my memory washed of the accomplishment, and I wish it wasn’t like that. But it’s almost like the moment after it’s done, or even before it’s done, I just start thinking, “Okay. What’s the next project? I hope I don’t screw it up.” The terror of screwing it up drives you forward.

Chris, are your successful commercials and “Flipside” enough for you?

Wilcha: I feel incredible relief that I finished the film. My daughter texted me today and she said, “I’m so proud that you followed through” and that was very meaningful. She saw me complete the task and finish the project. So, this film has been meaningful to everyone in my whole orbit.

The film is being theatrically released. Will it also be available on a streaming service?

Wilcha: We had a wonderful reception in Toronto. Every single streamer all of the sudden got curious. We had incredible sales agents but everyone passed and said, “This is not what the algorithm is rewarding right now.” I’ll never forget, one of the sales agents used this phrase, which just made me laugh and cry at the same time, “We are getting euphoric passes.” So, we are going down a much harder route now. We are theatrically distributing the film and trying to get people out on opening weekend. I’m on my social media trying to wrangle friends to get friends to go. It’s all word of mouth. So, in some ways, part of me wonders if this might actually be the best fate for a film of this scale, size, mood and tone. A theatrical release is a way for people to see it and to connect with it. That way it doesn’t just disappear into the ether of an algorithm or a search engine.

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