There is no surprise twist in Chris Wilcha’s Flipside, a documentary making its world premiere at the 2023 Toronto International Film Festival. This is not a true-crime doc or a story of unearthed family secrets. (Although there is lots of ephemera excavated after years of quasi-hoarding.) Instead of a twist, though, there is an audience awakening, one that takes a rather standard there-are-places-I-remember doc into surprisingly resonant territory. Ultimately, Flipside is a moving, funny, inventive film that may cause viewers to follow Wilcha’s lead and ask tough questions about their own lives. That is no small feat for a documentarian.

Of course, Wilcha is no novice. His first success, 1999’s The Target Shoots First, brought him rave reviews and modest fame. Wilcha shot it while working at Columbia House Records––yes, the “8 CDs for a penny” mail-order service many remember with great fondness. In Flipside, Wilcha shows the viewer his early-20s self, a young man who never left home without his Hi-8 camera and was part of the “demographic blip called Gen X.” Following the success of Target, he made a doc for MTV, helped Ira Glass turn This American Life into an acclaimed TV series, and became a parent.

“Then, the phone rings.” It was Judd Apatow with an offer for Wilcha to come to Los Angeles and make an behind-the-scenes documentary about Apatow’s Funny People. (Apatow is a producer of Flipside and appears onscreen.) Now living in L.A. with his wife and children, Wilcha found himself creatively adrift, eventually accumulating countless hard drives of unfinished projects. He started paying the bills by making slick TV commercials, a move that has caused him no end of agita. “Like a lot of people my age, I wake up one day to discover my temporary side gig is no longer temporary, or a side gig, and I’ve become the very thing I passionately wanted to avoid,” he explains. “I started the decade as a filmmaker. Now I’m a salesman.”

What flips the switch, so to speak, and brings back Wilcha’s passion for the documentary form is a return to Flipside Records in Pompton Lakes, New Jersey. This was his high school workplace, a job that was perfect for a young music fanatic. “Flipside was a clubhouse for misfits and fellow obsessives,” he says. Sometimes, Wilcha even chose records instead of getting paid. 

As the years have passed, Wilcha changed; Flipside didn’t. “The place remains exactly as I remembered it,” he says with resigned acceptance. The store is still bursting with albums, as well as the odd scent of meat. (The film explains why.) Flipside’s owner, Dan, has not changed much either. Wilcha finds that his old hangout is struggling, with only a few die-hard shoppers remaining. 

At this point in the documentary, it seems Flipside is going to focus on the economic realities of the retail side of the music business, a topic well-covered by Colin Hanks in his Tower Records doc All Things Must Pass. However, Wilcha now does something quite unexpected: he lifts the needle, hops into other stories, and moves Flipside Records to the pile of hard drives with “unfinished” films. Well, sort of; Flipside is not gone entirely from the film. After a decade, Wilcha returns to the store and to Dan, documenting how a hip vinyl shop competitor has opened nearby, driving sales at Flipside to even grimmer numbers. 

But that’s not really what Flipside, the movie, is all about. Ultimately, Wilcha’s film is concerned with figuring out your life’s purpose. “It wasn’t my fate to make things,” he concludes. “It was to market them.” To hammer home this point about the struggle to be true to oneself, Wilcha shares stories of other folks. Dan, the record man, is one of them. We also spend time with This American Life’s Starlee Kine and its host, Ira Glass; offbeat New Jersey comedy icon Uncle Floyd (a Flipside Records regular); legendary jazz photographer Herman Leonard; and even David Milch, the Deadwood creator now dealing with the effects of Alzheimer’s. 

Some of these stories carry more weight than others. We spend such a brief time with Starlee Kine that her motivations and goals fail to resonate. The Ira Glass section, in which the brilliant host of This American Life embarks on an unexpected live tour––centered on dancing (!)––feels dropped in from another film. It is not difficult to see how dancing Ira fits Wilcha’s thesis, and obviously there is a close connection between Glass and Wilcha after their work together. But it takes us out of Wilcha’s story and left me wondering what Flipside Dan and Herman Leonard were up to. Flipside‘s two dalliances with “celebrity”––in the forms of Ira Glass and Uncle Floyd––are certainly its weakest stretches. However, the Floyd section does provide an opportunity to include one of David Bowie’s late-period greats, “Slip Away.” Floyd was famously the song’s subject. 

Wilcha’s relationships––to his career, his family, his past––hit hardest. Viewers of a similar age (cough, me, cough) will undoubtedly connect with the filmmaker’s concerns. And it is also easy to care about Dan’s struggles with Flipside Records. Un-hip shops like this are dying, even as vinyl sales continue to grow. The great question that hovers over Flipside is simple: was it worth it? Dan never married or had a family, devoting himself to the store. Uncle Floyd never quite broke through and had multiple failed marriages. And Herman Leonard finally earned large-scale appreciation near the end of his life. So: was it worth it? In almost all instances do his subjects answer in the affirmative. And for Wilcha, turning to commerce over art is what has allowed him to spend so much time on unfinished projects in the first place. Making commercials will never be his passion, but it’s part of who he is. 

Flipside, then, starts as one thing and becomes something very different––a study of regret, the failures of nostalgia, and the value of seeing and (occasionally) preserving. (It’s also about the necessary act of throwing things out, eventually.) As Wilcha states near the film’s end, “This new thing, this new film, might even tie up all these years of loose ends.” Flipside might not put a neat bow on the stories of Dan the record man, Herman Leonard, Ira Glass, and others, but it deftly shows how each of these individuals and their passions matter to Chris Wilcha and far beyond.

Flipside premiered at the 2023 Toronto International Film Festival.

Grade: B

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