FLIPSIDE (TIFF 2023) – Review by Peg Aloi

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This unconventional documentary wound up really charming me. It begins with footage of photographer Herman Leonard, whose iconic images of jazz performers are seen in a gallery. Leonard is terminally ill, and talks briefly about his work. Then the interviewer, filmmaker Chris Wilcha (The Target Shoots First) shifts the focus to discussing his failure to finish this documentary project about Leonard because he ran out of time.

Wilcha portrays his early career as a filmmaker, waxing nostalgic over his early triumphs, including a personal documentary project for Judd Apatow (who produced Flipside), and a stint working on Ira Glass’ TV series based on his radio show This American Life).

Along the way there were also failures, and he makes the tough decision to eke out a living working in advertising. On a whim, he visits a record store in New Jersey where he worked as a teenager, and decides to make a film about it, to help the owner’s business thrive. That project also stagnates in limbo as Wilcha returns to LA to work, raises a family, and starts a number of other documentary projects, including one about a woman struggling with writer’s block.

Returning to Flipside Records after a decade, the situation has deteriorated and Wilcha struggles to reckon with having abandoned the project and with the trajectory of his creative life. Helped along by the subjects of his unfinished films, and utilizing an astonishing array of black and white imagery that veers from the pedestrian to the sublime, from dark to whimsical, Wilcha explores what it means to live an artistic life that repeatedly falls short of his dreams. He probes, often with irony and self-deprecating humor, the connections between ambition and motivation, desire and creativity, and the inescapable existential dread that accompanies the realization that time has passed faster than we could have believed possible.

What feels like a somewhat precious, self-absorbed odyssey at first ends up being a rather sobering and moving meditation that many artists will no doubt find achingly familiar.

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Peg Aloi

Peg Aloi was a freelance film critic for the Boston Phoenix from 1997-2013. She has taught film and media studies at Emerson College and SUNY New Paltz. She's organized conferences, edited scholarly anthologies, and been a script consultant on feature films. She is currently a freelance film and TV critic.