‘Flipside’ Review: Finding Purpose in Failure

This review was made possible by an advance screener of Flipside. Flipside is now showing at IFC Center in NYC, and begins rolling out to select theaters June 7. 

If you’re anything like me, your first thought upon hearing about this documentary directed by and starring Chris Wilcha is probably, “Okay, who is this guy?”

Pulling up his iMDB you’ll find he directed a few TV specials, a stand-up comedy special, and most notably, the TV adaptation of This American Life. Your next thought, in an attempt to connect with an idea of why you should watch Flipside, is likely, “Well what’s this about?” The elevator pitch would be along the lines of… It’s Chris Wilcha visiting the small-town record store of his youth and hoping to revive it, while taking a trip down memory lane, looking at his abandoned documentary projects. The reality? It’s about a lot of things, and you’re asking the wrong questions. Unlike most documentaries, the creator and the subject, while still significant, are not the defining factors in why you should watch this. The key is actually the audience – what type of person needs to see it. Flipside is made for creatives, especially those who struggle with roadblocks, regrets, change, and mortality.

Flipside kicks things off with a young, fresh-faced Wilcha – a 22-year old carrying a Hi8 camera everywhere he goes in New York City, in 1993. His voiceover narrates a speedy walkthrough of his life’s events, from his early hit doc The Target Shoots First, to his family growing amidst other film endeavors, to their move to LA so he can shoot a doc about the making of Judd Apatow’s Funny People. From there, days turn to weeks, weeks turn to months, months turn to years, and he finds himself leaning more and more into passionless side gigs, while hard drives full of incomplete documentaries collect dust in his office. This first act comes to a head when his focus shifts to Flipside Records, a small shop he worked at as a teen in New Jersey. We get to know the cozy store, the owner, and some of the people who shop there.

This is where things start to become deeply absorbing. Flipside Records continues to be used as a centerpiece that is returned to throughout the film, but Flipside isn’t really about it. It’s about Wilcha reconciling his regrets with his reality, and using the record store as a sort of touchpoint he keeps returning to, to do so (while also paying respect to the beloved place by shamelessly promoting it). Whereas the first act of the film was a straightforward, linear explainer of Wilcha’s life, the second act shifts into an ebb and flow determined by themes and ideas, rather than a timeline of events. He focuses on key people in his life – his parents, his collaborators, his unfinished doc subjects – to explore ideas such as growing up, destiny, the American dream, work-life balance, and so much more.

I previously mentioned Judd Apatow, and he’s actually one of the people in Wilcha’s life who is interviewed here (and he serves as producer). From there, a tapestry of creative, passion-driven souls is woven throughout the doc. Jazz photographer Herman Leonard provides perspective on legacy. Deadwood writer David Milch grants importance and belonging to both young and old. This American Life’s Ira Glass finds emotional refuge in bold, new pursuits. The way these people and stories (and so many more) are interconnected or linked to Wilcha’s life is masterfully constructed before us, not just from footage for this doc, but by using footage from the docs that never saw the light of day. Through this, Wilcha finds catharsis by using his failures to build a personal creative victory: Flipside. This somewhat meta storytelling idea feels like the perfect arc to cap off a film that lives and breathes amid the creative process.

‘Flipside’ – Final Thoughts

Flipside is a documentary by a struggling creative, about struggling creatives, for struggling creatives. It’s made for the middle-aged filmmaker who wakes up and realizes he’s not doing what he loves. It’s made for those who feel their life’s work has been overlooked. It’s made for the 23-year old writer who has his whole life ahead of him but has trouble fathoming a future where he can keep pursuing his passions while also wanting to start a family. Chris Wilcha has woven an emotionally touching, philosophical, introspective web of stories for anyone with a passion to create, and I cannot stress enough its importance for that audience. It may not give you the answers you want, but it will give you the advice you need. Watch it, laugh a little, ponder over it a while, and let Flipside seep into your soul.

Flipside is now showing at IFC Center in NYC, and begins rolling out to select theaters June 7. Check out the trailer below.