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, 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 as women they encounter during their trip.

Sideways premiered at the Toronto International Film Festival on September 13, 2004, and was released in the United States on October 22, 2004. It received widespread acclaim from critics and is regarded as one of the greatest films of the 2000s. At the 77th Academy Awards, the film was nominated for Best Picture, Best Director, Best Supporting Actor (Haden Church), Best Supporting Actress (Madsen), and Best Adapted Screenplay, the last of which it won.