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TIFF 2023 Review: ‘Flipside’ Suggests the Finish Line Isn’t the Point

For a film about accepting things not turning out as you once hoped, this documentary is strikingly inspirational and aspirational.

TIFF
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At one moment in Flipside, director Chris Wilcha recalls feeling guilty about almost calling himself a documentary filmmaker. At that point, he felt like he was, more than anything, a director of commercials and advertisements, his days of being a serious documentarian behind him. 

Wilcha is more than just an advertisement director, of course. All of the personal footage included in the Frankenstein-ed, multi-storied Flipside reveals that Wilcha is, happily, a father and a husband with a life he seems to be very aware is filled with great joy — but, now approaching middle age, it just wasn’t where Wilcha expected he’d end up. 

Wilcha’s 1999 documentary, The Target Shoots First, was a major success: he won awards, he got job opportunities, he was even seduced to Los Angeles by promises of work with Judd Apatow. But due to a combination of needing to make money and a struggle with the artistic process, Wilcha ended up making lots of corporate sell-out ads while gradually accumulating unfinished documentary projects. 

Flipside is a mosaic of these unfinished projects, creating a retrospective meditation on art and middle age. It’s mostly made up of Wilcha’s documentaries that could have been, some spanning over a decade of on-and-off work. 

There’s footage of Herman Leonard, a famous jazz photographer, in his final days before succumbing to cancer. There’s a story about a woman in the midst of a perennial writer’s block. But the footage most pivotal to this documentary is of Dan, the owner of a beat-up, dusty, charming record shop (the titular Flipside) that Wilcha worked in as a teenager. 

Some days, record shop owner Dan doesn’t even make 15 dollars. He doesn’t want to make a website, he doesn’t want to fix the store sign, and he occasionally hoards records he really loves in the basement instead of selling them. Dan lives stagnantly, invested in just existing instead of pushing toward progress. He is, at moments, an inverse mirror image of Wilcha: while Wilcha suffers under a sense of stillness — of treading water — Dan is unconcerned about the sense of sameness in his life and work.  

Flipside is deliciously bittersweet. Like a collage or quilt of ghosts of art projects past, it suggests that the work is sometimes the point, regardless of whether it becomes some finished, polished thing. Maybe we’ll get lucky and it’ll lead us toward some grand project that slaps it all together (though even that can take half a dozen “failed” attempts and decades of our life), or maybe it’s just about the process. 

What’s fascinating about Wilcha is that he talks so much about unfinished works, about all the things he did “instead” of becoming a serious or legitimate filmmaker — things like having kids, making commercials, and helping out other artists. But paradoxically, Wilcha’s endless footage of all of the things he did “instead” reveals that he really has been doing what he’s loved this whole time. It seems that the notion that he’s not a legitimate documentarian is a belief that’s internal more than anything — because if Wilcha does one thing, it’s document. 

Flipside does not suggest rushing toward our goals, nor does it suggest totally repressing the inherent grief of a life that inevitably turns out differently. For a film about accepting things not turning out as you once hoped, Wilcha’s documentary is strikingly inspirational and aspirational. It makes you want to make something for the sake of it — or, at the very least, start making something. The point seems to be that the finish line isn’t the point. 

Flipside is less of a midlife crisis and more of a midlife comfort. It’s a bittersweet love letter to the gradual accumulation of real life, with all of its starts and stops, and of retrospective successes discovered in present failures.

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