'' Sideways '' is a 2004 American 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
Toronto International Film Festival
2004 Toronto International Film Festival
Sideways