Directed by Alexander Payne, Sideways follows Miles (Paul Giamatti), who is distressed about his lack of success as a novelist, and Jack (Thomas Haden Church), an equally unsuccessful actor with a rapidly approaching wedding. In a last-ditch effort to sow their wild oats, Jack and Miles take off on a final road trip to California's wine country the week prior to Jack's wedding. Both men have goals for the vacation -- Miles wants to turn Jack on to the art of wine tasting, while Jack is concerned with exploiting his last days as a bachelor -- but when the two men come across two fascinating women (Virginia Madsen and Sandra Oh), the duo is forced to examine their morality, and if maturity isn't such a depressing prospect -- at least, for one of them.