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Sideways is a 2004 American comedy-drama film written by Jim Taylor and Alexander Payne and directed by Payne. A film adaptation from Rex Pickett's novel of the same name, Sideways follows two men in their forties, Miles Raymond (Paul Giamatti), a depressed teacher and unsuccessful writer and Jack Cole (Thomas Haden Church), a past-his-prime actor, who take a week-long road trip to Santa Barbara County wine country to celebrate Jack's upcoming wedding. Despite his impending marriage, Jack has a romantic fling with a local wine pourer, Stephanie (Sandra Oh), and tells her he is in love with her. Jack persuades Miles to date Stephanie's friend, a server named Maya (Virginia Madsen), whom Miles knows. The double romance blooms until Miles lets slip that Jack is getting married at the end of the vacation, which causes both women to angrily break off their relationships with the men. Payne and Taylor won multiple awards for their screenplay. The principal actors and actresses received accolades for their performances. Sideways won the Academy Award for Best Adapted Screenplay, and was nominated for four other awards including Best Picture.
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