The film, Sideways, has been critically acclaimed for its screenplay, cinematography, and acting. Criticism from some quarters centered on the implausi-bility of the story, notably regarding the attractiveness of the two male lead roles to the two female supporting characters. Miles, the schoolteacher/writer, represents an individual with the hysterical (shy, effeminate, “foppish”) subtype of histrionic personality disorder; and Jack, the actor, depicts the histrionic (hyper-masculine, “Don Juan”) subtype. Similarly, Stephanie, the barmaid, and Maya, the waitress/student, may be seen as even more polar representations along the spectrum of the female hysteric. These characters were blocked in various stages of psychosexual development, most notably seen in the adolescent behaviors of Miles and Jack. The wine country setting, the exposition of wine culture, and associated bacchanalian drama juxtaposed to developmental metaphors lend texture and depth to the superficial, comedic aspects of the film.