Clay Hewitt (Vince Vaughn) is a young drifter with only a few dollars to his name. When he asks Dellah Potts (Kate Capshaw) a widow who inherited a cattle empire, for a job, she gives him one, but also invites him into her bed. While he turns her down, he does become concerned about her withdrawn son, Flyboy (Jeremy Davies). with the help of Kitty (Ashley Judd), a local girl he becomes involved wit, Clay tries to help Flyboy break from his shell only to find his problems run deeper than he could have expected. / Intricately stepping back and forth in time a revealing the story from each character's perspective. Wicker Park is an intense psychological drama about a man caught in an obsessive search for a woman he fell deeply in love with a woman who then vanished without a trace.