Sandra Oh and Virginia Madsen also star as women they encounter during their trip. ![]() ![]() ![]() A film adaptation of Rex Pickett's 2004 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. Sideways is a 2004 American comedy-drama road film directed by Alexander Payne and written by Jim Taylor and Payne.
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