A portrait is a delicate transaction: the subject might look at it and, shocked, see not himself but how the artist feels about him. One of the most audacious character studies to come out of the American underground cinema is Shirley Clarke’s Portrait of Jason (1967); like many portraits, it’s most fascinating as a document of a relationship. Clarke, a Jewish heiress, made a name for herself in New York directing the hard-edged urban drama The Connection (1962); one evening in December 1966 she invited Jason Holliday, a jocular, 42-year-old gay hustler, up to her penthouse apartment at the Chelsea Hotel and, with a film crew, spent 12 hours filming him against one wall as he held forth about his wild life. Clarke never appears on camera, and her questions for Holliday are short, simple, and infrequent. Yet the finished feature, running 105 minutes, speaks volumes about what these two people had in common—and what they didn’t. Continue reading >>