Sideways is a 2004 American comedy-drama road film directed by Alexander Payne and written by Jim Taylor and Payne. A film adaptation of Rex Pickett's 2004 novel of the same name, Sideways follows two men in their forties, Miles Raymond , a depressed teacher and unsuccessful writer, and Jack Cole , 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 as women they encounter during their trip. The film premiered at the Toronto International Film Festival on September 13, 2004, and was released in the United States on October 22, 2004. Sideways received widespread acclaim from critics and is regarded as one of the greatest films of the 2000s. It was nominated for Best Picture, Best Director, Best Supporting Actor and Best Supporting Actress , winning Best Adapted Screenplay at the 77th Academy Awards.