With his remarkable talent for gritty yet sophisticated scat singing, Chicago vocalist Ron Cooper could have been a star, or at least a steadily employed journeyman musician. Instead he wound up on the street. A familiar figure along the byways of Uptown, Wicker Park, and Rush Street, Cooper could be found delivering his smoky, rhythmically subtle renditions of jazz standards in clubs like the Green Mill and the Gallery Cabaret—or in the Division Street station of the Blue Line subway, whose cars he frequently rode all night so he wouldn't have to sleep in a shelter. Director-cinematographer Dustin Grove shot this intimate 2010 documentary over a period of two years, leading up to the subject's death in 2007 at age 53; the video celebrates Cooper's gifts but also confronts his struggles with alcoholism, homelessness, and ill health. Commentary by local jazz notables (including Von Freeman, Fareed Haque, and Joanie Palatto) illuminate this enigmatic man, who lived for music but had trouble functioning in the "real" world.