In Flipside, Director Chris Wilcha Examines the Creative Life

Regrets. Chris Wilcha has a few.

He has built a successful career as a director making documentaries and commercials over the last 20 years. But, like any creative person, Wilcha has started a number of projects—in his case, documentaries—that remain unfinished for reasons ranging from lack of inspiration to a dearth of funding. And this nags at the Gen-Xer as he approaches mid-life.

Channeling regret into action, Wilcha pours his angst—and, cleverly, footage from unfinished docs—into Flipside. With Judd Apatow as executive producer, the film made its world premiere at the 2023 Toronto International Film Festival last month, and will mark its U.S. launch at DOC NYC on Nov. 12.

Flipside finds Wilcha returning home to New Jersey, where he tries to save the struggling Flip Side Records & Tapes, the store where he worked as a teenager. This begets a journey of self-examination into Wilcha’s career as a storyteller, allowing him to incorporate footage of jazz photographer Herman Leonard, podcast producer Starlee Kine and TV writer/producer David Milch (a force behind like NYPD Blue and Deadwood, now living with Alzheimer’s).

Though Wilcha’s theme here is unfinished work, it should be noted that he has completed several documentaries, including The Target Shoots First, Another Day, Another Time and Knock Knock, It’s Tig Notaro. 

Wilcha won an Emmy in 2008 for Outstanding Directing for Nonfiction Programming for his work on the television adaptation of NPR’s This American Life.

In the ad world, the director, repped by Park Pictures, famously lensed the Storytellers launch film for the Apple TV+ as well as spots for Chevy, Phillips 66 and Facebook.

Below, Wilcha gauges the reaction to Flipside and parses the concept of selling out. He also reveals the kind of work he’d love to do.

MUSE: After Flipside screened at TIFF, were you approached by audience members who had regrets about their own unfinished projects? Did you take on the role of creative therapist? 

Chris Wilcha: What was startling after TIFF is that people would come up to me and be like, “Tell me how to finish my project.” One guy was a college professor, another person was a student. My wife was joking that I could maybe pivot and become a creative life coach. Maybe there’s a new career path here—I could help people with their unfinished projects.  

Have you ever see the Kristen Johnson documentary Cameraperson? 

Yes!

Like you, Johnson used material she had shot for unrelated films to tell a story that she never expected to tell with that footage. It must take so much work make a film this way. Did Flipside seem like an impossible task for you and your editors?

The process of making this, I’m just being brutally honest, was a form of torture. Now, it was a torture that I’m addicted to, which is the torture of creative work: You’re failing, and you’re failing, and you’re failing, and then you make a decision, or two pieces of footage sit next to each other, and all of a sudden the path forward opens up. And these incremental successes start to accumulate. 

It took constant revision. We kept re-doing and moving parts around and re-writing the voiceover and honing. It was labor intensive. But then there’d be a breakthrough where you were like, “Wait a minute. Actually, Herman Leonard says a thing that echoes [themes emerging later] … and his voice can recur. And what if we did that with David Milch? And what if we had Starlee come back and echo something she said?” And all of a sudden, you’re getting into it, and you’re like, “Oh, we’ve built an algorithm that’s kind of working.” It was very much moving puzzle pieces around until the last minute.

In your earlier documentary, The Target Shoots First, you are working in corporate America at Columbia House, and you resist the idea of becoming a sellout. That idea comes up again in this new film. Some people working in advertising struggle with the idea of being sellouts. But some view it as a creative outlet just as valid as any other. How do you feel about making commercials?

It is a complete privilege to be able to do commercial work. I don’t get into the details of what it’s actually like to pursue it [in the movie]—the competitiveness, the bidding against three, four, five other directors, the way you can lose three [bids] in a row and think you’re never going to work again, and then all of a sudden you get another one. It is such a rollercoaster ride making a living this way. But it’s also incredibly thrilling. 

I think what I was trying to get at in the movie was not to disparage commercial work, but to say that it fell out of balance at a certain point. The intent was to try to balance the two. The intent was to do the commercial stuff well and to never phone it in. But it was also about doing the occasional documentary of my own. And what became very tricky was that balance.

Are there any types of ads or projects you’re dying to direct?

One thing that always slightly broke my heart was that I was music obsessed, just a diehard fan. And, for some reason, I missed the train on everything music related. Music videos had sort of become obsolete by the time I started directing. And there was a renaissance a few years ago where artists were doing slightly more ambitious music videos again.

I did one music documentary that was an incredible experience. It was called Another Day, Another Time. The Coen brothers were putting on a concert that was connected to the film they were releasing, Inside Llewyn Davis. It was this whirlwind experience. But my larger point, just to answer your question: I felt like music stuff completely passed me by. I still haven’t been able to do a proper music documentary or video.