Sideways

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 (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. 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 (Haden Church) and Best Supporting Actress (Madsen), winning Best Adapted Screenplay at the 77th Academy Awards. Plot Miles Raymond is an unpublished writer, a wine aficionado, and a depressed, middle-aged English teacher living in San Diego. He takes Jack Cole, his soon-to-be-married actor friend and former college roommate, on a road trip through the Santa Ynez Valley wine country. Jack now does commercial voice-overs and plans to enter his future father-in-law's successful real estate business. Soon after the trip begins, Miles insists on stopping to see his mother in Oxnard, as it is the day before her birthday. He steals nine hundred dollars from her room that night. The men sneak out early the next morning to avoid the birthday gathering. Miles wants to spend the week relaxing, playing golf, and enjoying good food and wine. However, much to Miles' consternation, Jack is on the prowl and wants one last sexual fling before settling into domestic life. In the wine country, the pair dine at The Hitching Post II. Jack sees that Maya, a waitress with whom Miles is casually acquainted, is interested in Miles; Miles thinks she is only being professionally friendly. Jack lies to Maya that Miles' manuscript has been accepted for publication, although it is only being considered. At a wine tasting the next day, Jack arranges a double date with a wine pourer named Stephanie, who is also acquainted with Maya. During the date, Miles gets drunk and telephones Victoria, his ex-wife, after learning from Jack that she has remarried and will be bringing her new husband to Jack's wedding.