For decades, he has been jumping out of planes with a movie camera to create jaw-dropping moments for extreme sports shows, TV commercials, and Hollywood blockbusters. Now in his early sixties, he looks back on the triumphs and tragedies that shaped his life as he tries to pull off the aerial stunt he’s never been able to achieve.

Jennings uses the open air like Dalí used canvas to create surreal and unforgettable images. He’s long been possessed by the vision of an open-top automobile falling from the sky. He wants to film it with four passengers sitting in the car, like a comic book scene brought to life. It might sound like lunacy, but the film reveals the poignant life journey that motivates Jennings to bring his dream to reality.

Growing up with ADHD, Jennings preferred the outdoors to school, earning him the nickname “Joe Dirt.” In college, he discovered his two great loves: his wife, Sissy, and skydiving. He teamed with Rob Harris and they became the dynamic duo of pioneering aerial tricks for ESPN’s X-Games. That led to a continual escalation of what was possible.

Beyond the thrill-seeking, filmmakers Marah Strauch and Bryce Leavitt explore Jennings’ other layers, including how he’s coped with his peers’ fatal accidents, his clinical depression, and balancing work with family. The film teaches us how to reach for the highest heights and how to deal with the pull of gravity.

Thom Powers