Sideways (2004) is a comedy-drama film directed by Alexander Payne and written by Payne and Jim Taylor. It follows two men, Miles (Paul Giamatti) and Jack (Thomas Haden Church), on a week-long road trip through California's wine country.
From Wikipedia
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 2004 novel, 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.