In Chris Wilcha’s film, Judd Apatow, David Milch, regional TV icon Uncle Floyd, and a cherished New Jersey record store come together in a contemplation of both life’s setbacks and the value of a fulfilling existence.
Measuring one’s life by achievements, the gathering of awards and recognition, and personal and career triumphs, often seems like a clear marker of success. However, it becomes more challenging to gauge life not necessarily by failures, but by untapped potential, partially finished endeavors, or neglected possessions, and still declare, “In spite of, or maybe even because of this, there is success.”
In his latest documentary, “Flipside,” Chris Wilcha confronts this second challenge by presenting an autobiographical account of how a life filled with apparent disappointments and failures can actually be a life lived to its fullest. When viewed at an inopportune moment or from a certain perspective, “Flipside” may come across as somewhat self-centered, although in a manner that resonates with many audiences. However, when considered as a whole and with some contemplation, it emerges as a nearly profound and philosophical testament to finding contentment in the incomplete aspects of life.
On paper, Chris Wilcha’s life doesn’t seem like a failure at all. His initial documentary, “The Target Shoots First,” received acclaim on the festival circuit and provided a quintessential Gen X perspective on his attempts to sell out while working for Columbia House in the 1990s. He even earned an Emmy for his involvement in adapting Ira Glass’ “This American Life” for television. Moreover, he has maintained a steady career as a commercial director for some of the world’s largest brands, and his family life appears picture-perfect.
However, beneath this seemingly successful exterior, Wilcha has a stash of hard drives filled with footage from unfinished documentaries and unrealized artistic projects that were put on hold for various reasons. All the while, his professional life revolved around what could be seen as glorified marketing. For a storyteller who came of age in a generation that, at least for a time, embraced the no-compromise cynicism of films like “Reality Bites,” this situation feels like a letdown. Despite his father’s successful career in marketing, it was a path Wilcha had hoped to avoid.
“Flipside” revolves around Wilcha’s return to his hometown in New Jersey, where he is grappling with two monuments that blur the line between collecting and hoarding. One is his childhood closet, filled with albums, books, concert shirts, and mementos from his youthful self. The other is Flip-Side Records & Tapes, a vintage record store where he once worked, now struggling and reminiscent of a museum more than a retail establishment from a bygone era.
While struggling to discern the worth in his fairly well-organized chaos and engaging in conversations with Flip-Side’s owner, Dan, as well as some of Wilcha’s former friends and colleagues, he delves into the footage from his unrealized documentaries. Surprisingly, the values explored in these endeavors, though more spiritual than financial, all converge.
Wilcha’s collection of incomplete projects in this cinematic graveyard is a fascinating assortment. It includes interviews with the legendary jazz photographer Herman Leonard (you’ve definitely seen some of his iconic images) conducted shortly before his passing. There’s also peculiar material from an Ira Glass touring show where the host participated in fully choreographed dance performances.
Moreover, there are documentaries that could have been initiated and are connected to other unfulfilled endeavors. One example is Uncle Floyd, a television personality and New Jersey icon who has had unexpected ties to Saturday Night Live and David Bowie. Wilcha’s link to Herman Leonard came through his connection with Deadwood creator David Milch, which in turn emerged from Milch’s association with Judd Apatow, with whom Wilcha collaborated on a documentary about the making of “Funny People.” There’s a complex web of editing that intertwines these unfinished documentaries within “Flipside,” uniting them as different aspects of Wilcha’s life. The notion that what may appear as loose ends from our past could potentially lead to unforeseen resolutions is both pleasantly reminiscent of Dickens and remarkably uplifting when contemplated.
When watching “Flipside,” you might find yourself thinking that many of the films within it, which were once left unfinished, could be more captivating as standalone features than the partial autobiography or the narrative centered around a beloved old record store. Particularly, the segments featuring David Milch, who is battling Alzheimer’s and is interviewed alongside his wife, Rita, as well as Judd Apatow, may leave you craving more content. However, that’s precisely the point. Chris Wilcha himself had also believed that these segments would be more compelling as independent films. Yet, the care and consideration with which Wilcha incorporates Milch, Leonard, and Uncle Floyd into the documentary, extracting something aspirational from their attitudes and spirits without making it all about him, is thoughtful and occasionally inspiring.
In “Flipside,” none of the individuals are living the exact lives they had initially envisioned. Even Apatow, who serves as an executive producer, is linked to Wilcha through a movie about a stand-up comedy career that he never pursued. As Leonard aptly puts it, “There will always be circumstances.” How one navigates those circumstances, whether by conquering them, adapting to them, or learning from disappointment and moving forward, can depend on perspective, determination, or simply luck.
This narrative can serve as a metaphor not only for life’s pursuit in general but also for the process of creating art, or even the universally relatable experience of sorting through the clutter and chaos of one’s life and discovering hidden treasures amidst the mess. You might not connect with the segments in “Flipside” that revolve most around Wilcha himself, but in just 96 minutes, the film effectively argues for the idea of crafting something new and meaningful from the unused documentary footage equivalent in your own life.