Jacoby assembles thrilling footage of young Hambleton painting his "shadowmen" on the Lower East Side in 1981; these lean, life-sized, brush-painted silhouettes loomed in dark corners of the cities, less graffiti than presences. The film then follows Hambleton's life chronologically, nudged along with revealing interviews with the artist himself, plus the people who knew him best. At the height of his fame, the restless, irascible, never-satisfied painter turned from his shadowmen to sea- and landscapes, a drug-fueled search for the sublime that art buyers weren't interested in. Soon, Hambleton was crashing in hovels, celebrating his occasional sales with heroin and caviar. (We see scarifying video of some of his homes.)
In 2009, Hambleton enjoyed a comeback, touring the world with new shadow art that sells to celebrities and Wall Street swells and oligarchs, none of whom much impress Hambleton. In 2013, a Moscow businessman offers the then-homeless Hambleton a trade that might interest Robert Mueller. For one painting a month, Hambleton could live at the Trump Soho. Six months in, we learn, that Hambleton — true to form — got booted for trashing his room.