Gus Van Sant's 1990 feature, his best prior to Elephant, is a simultaneously heartbreaking and exhilarating road movie about two male hustlers (River Phoenix and Keanu Reeves) in the Pacific northwest. Phoenix, a narcoleptic from a broken home, is essentially looking for a family, while Reeves, whose father is mayor of Portland, is mainly fleeing his. The style is so eclectic that it may take some getting used to, but Van Sant, working from his own story for the first time, brings such lyrical focus to his characters and his poetry that almost everything works. Even the parts that show some strain—like the film's extended hommage to Orson Welles's Chimes at Midnight—are exciting for their sheer audacity. Phoenix was never better, and Reeves does his best with a part that's largely Shakespeare's Hal as filtered through Welles.
Director: Gus Van Sant
Writer: William Shakespeare and Gus Van Sant
Producer: Laurie Parker
Cast: River Phoenix, Keanu Reeves, James Russo, William Richert, Rodney Harvey, Chiara Caselli, Michael Parker, Jessie Thomas, Flea and Grace Zabriskie