Sideways is a 2004 American black comedy drama film directed by Alexander Payne and written by Jim Taylor and Payne. A film adaptation of 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. Sandra Oh and Virginia Madsen also star. The film premiered at the Toronto International Film Festival on September 13, 2004, and was released in the United States on October 22, 2004.
Payne and Taylor won multiple awards for their screenplay, with the cast also receiving accolades for their performances. Sideways won the Academy Award for Best Adapted Screenplay, and was also nominated for Best Picture, Best Director, Best Supporting Actor (Haden Church) and Best Supporting Actress (Madsen).