Sideways is a 2004 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 year old 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 actresses Virginia Madsen and Sandra Oh, playing local women who become romantically involved with the men, all received accolades for their performances.
Miles Raymond (Giamatti) is a single divorcé, unpublished writer, wine-aficionado and middle school English teacher, living in San Diego, who takes his soon-to-be-married actor friend and college roommate, Jack Cole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. Along the way, Miles stops to see his mother for her birthday, and also to steal some cash that she keeps hidden. During dinner it becomes clear 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, and her friend Stephanie (Sandra Oh), a winery employee. Jack quickly arranges a double date. Neither man tells the women about Jack's imminent marriage. Jack embarks on a whirlwind affair with Stephanie while Miles hesitantly tries to connect with Maya. After some fumbling and awkward moments, Miles and Maya sleep together, and he gives her a copy of his unpublished manuscript. The following day, Miles accidentally lets slip to Maya the fact that Jack is soon to be married. 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 causes a scene in a winery, drinking the contents of the spittoon in an attempt to drown his sorrows. Miles hopes that the altercation with Stephanie has quieted Jack's hormonally charged mindset, but Jack meets Cammi, an overweight waitress who recognizes him from his acting work, and he goes home with her. Miles is awakened in the middle of the night by Jack, who has returned to the motel panicked and naked. He breathlessly tells Miles that Cammi's husband caught him in flagrante delicto and he had to run, leaving behind his clothes and a wallet containing irreplaceable, custom-made wedding bands. If he returns home without the rings, he says, his fiancee will dump him, and that will destroy him. He tearfully begs Miles to retrieve the bands. Miles reluctantly agrees to help, sneaking into Cammi's house while she and her husband are having sex. He retrieves the wallet, but is furiously pursued out of the house by Cammi's naked husband, narrowly escaping. As a cover story to explain his broken nose, Jack fakes an accident, runs Miles' car into a tree (and eventually into a ditch). Jack's fiancee and her wealthy family believe the tale and offer him support and sympathy. At the wedding, Miles encounters his ex-wife, Victoria, who has remained friendly with Jack. She introduces Miles to her new husband and tells him that she is pregnant. Miles, finally forced to face the fact that Victoria will never return to him, skips the reception to go home and get his most prized bottle, a 1961 Château Cheval Blanc. He had purchased the wine so that he and Victoria could drink it together on the 10th anniversary of their wedding; instead, he drinks it alone, unceremoniously, from a foam cup at a fast-food restaurant. About a month later Miles arrives home to find that Maya has left a message on his answering machine. She thanks him for a letter he wrote to her and says that she needed some time to think about what happened. She also says that she enjoyed his book and thinks that he is an excellent writer, although she expresses some confusion regarding the novel's ending. In particular, she wonders if the central character is based on Miles, and whether the character commits suicide. The message also reveals some details that might help to explain Miles' bleak perspective on the world. She invites him to see her if he ever returns to the wine country. The film ends with Miles traveling back to Santa Ynez Valley and knocking on Maya's door.