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Hard-drinking Jeff Butler can't hold a job and thinks God is against him. When a wealthy old lady confuses Jeff for her long-lost nephew and invites him to live in her house, Jeff thinks he's found the scam of his dreams. But as strange events unfold, Jeff finds himself more confused than his would-be victim.

From DaVinci's wing sketches to the day hang gliding became an official sport in 1971, "The Flyingest Flying" offers a detailed evolution of this purest form of flight, as well as unique glimpses of the everyday people who pursue it. The film features rare interviews with such key figures as Francis Rogallo, the NACA (pre-NASA) engineer who designed the first flexible wing, to enhance his hobby of kite flying; John Dickenson, the Australian water skier who melded Rogallo's wing with the A-frame control bar still in use today; and fearless early promoters Bill Bennett and Bill Moyes, who barely survived their countless, creative attempts to introduce the fledgling sport to the world. Also featured are director Josh Criss' experiences at a hang gliding "flight park" in Manquin, Virginia, and the varied people who fly there. Along with the filmmaker's own journey from tentative student to soaring pilot, the film chronicles the struggles of another student, though multiple lessons, in her quest to solo at high altitude.