“Every life is a trip,” says the legendary photographer Herman Leonard at the beginning of Chris Wilcha’s documentary Flipside.
“You are the captain of your boat.” In these opening moments, Flipside seems like it’s going to explore the life of Leonard, yet Wilcha—who helped adapt This American Life for television—zooms out even further, focusing on this statement by Leonard, and instead of looking at any one subject, decides to focus on larger ideas like the regrets we all have in life, how our dreams shift and evolve over the years, and how the unexpected can often be greater than what we expected.
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