Sideways is an American comedy-drama film written by Jim Taylor and Alexander Payne and directed by Payne. Adapted from Rex Pickett's 2004 novel, Sideways follows two forty-something men, portrayed by Paul Giamatti and Thomas Haden Church, who take a week-long road trip to the wine country of Santa Barbara. Payne and Taylor won multiple awards for their screenplay. Giamatti and Church, as well as supporting actresses Virginia Madsen and Sandra Oh, who played two local women who become romantically involved with the men, all received accolades for their performances in the film.
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Sideways is an American comedy-drama film written by Jim Taylor and Alexander Payne and directed by Payne. Adapted from Rex Pickett's 2004 novel, Sideways follows two forty-something men, portrayed by Paul Giamatti and Thomas Haden Church, who take a week-long road trip to the wine country of Santa Barbara. Payne and Taylor won multiple awards for their screenplay. Giamatti and Church, as well as supporting actresses Virginia Madsen and Sandra Oh, who played two local women who become romantically involved with the men, all received accolades for their performances in the film.
Plot
Miles Raymond (Giamatti) is a single divorcé, unpublished writer, and wine-aficionado living in San Diego, who takes his soon-to-be-married actor friend and college roommate, Jack Cole (Church), on a week-long road trip through Santa Ynez Valley wine country. Miles wants to drink wine, eat fine food, play golf, enjoy the scenery, and send Jack off in style. However, Jack is more interested in "sowing his wild oats" and having one last sexual fling. On their way to Santa Ynez, Miles stops to see his mother for her birthday, and also to steal some cash that she keeps hidden in a drawer in her bedroom. During dinner with his parent it is heavily implied that Miles still has strong feelings for his ex-wife, Victoria.
Soon after their arrival in wine country, they encounter Maya (Virginia Madsen), a waitress at Miles' favorite restaurant that he has secretly harbored a crush on, and her friend Stephanie (Sandra Oh), a winery employee, and Jack quickly arranges a double date for the four of them. Neither tells the women about Jack's imminent marriage. Jack quickly becomes involved with Stephanie, which interferes with Miles' plans for the trip, but Miles, who is quite familiar with Jack's impetuous nature, lets it go, convinced that the relationship will be short-lived. Meanwhile, he begins to casually court Maya, with Jack's encouragement. After some awkward but intimate moments they sleep together.
The following day Miles accidentally lets slip to Maya the fact that Jack is soon to be married, and she tells Stephanie, who attacks Jack, breaking his nose. Miles also receives the crushing news that his novel has been rejected yet again, and his agent advises him that it is probably futile to keep resubmitting it. He hopes that the altercation with Stephanie has quieted Jack's hormonally charged mindset, but Jack meets Cammi, a heavy-set waitress who recognizes him from his acting work, and he goes home with her, leaving Miles. Back at the hotel, Miles is awakened in the middle of the night by Jack, who was caught in bed with Cammi by her husband, and had to run naked back to the motel. In doing so, he left behind his wallet and custom-designed wedding bands. Miles reluctantly agrees to help, sneaking into the apartment as the couple are having sex. He retrieves the wallet, but is chased by Cammi's naked husband, narrowly escaping.
