- 2 hr 3 min
Forty-something Miles Raymond (played by Paul Giamatti) is a failing writer, wine lover, and a despondent teacher of middle school English living in San Diego. Miles decides to take Jack Cole (played by Thomas Hayden Church), his soon-to-be-wed friend, actor and college roommate on a road trip across the wine country of Santa Barbara County's Santa Ynez Valley. Miles just wants to relax and live well while Jack wants one final fling. In wine country, Miles and Jack meet Maya, a waitress as Miles' favorite eatery, and Stephanie, an employee for a local winery. They hit things off and plan a double date, while concealing Jack's status as a fiancé. Jack cheats with Stephanie while Miles and Maya form a connection. Miles blurts out the truth about Jack's marital status to Maya. Maya angrily dumps him and informs Stephanie of the situation. Stephanie reacts by breaking Jack's nose against her motorcycle helmet. Miles makes a scene at a wine tasting after learning that yet another one of his manuscripts was shot down while Jack hooks up with Cammi, another waitress. Jack gets further into trouble when Cammi's husband comes home early, forcing him to vacate the place naked and without his wallet, where he stored the wedding rings. Miles sneaks into Cammi's place, barely making it out with Jack's wallet. In order to create an explanation for the broken nose, Jack runs Mile's vehicle into a ditch to mimic front-end damage as evidence of being hurt in an accident. At Jack's wedding, Miles encounters Vicki, his now-pregnant ex-wife, as well as her current husband. Aware that Vicki is with child, Miles realizes she will never come back to him and drinks his favorite wine out of a coffee cup within a fast food joint. Later, he receives a notice from Maya which states that she loves his manuscript and wants him to visit her again. The final scene in the film has Miles knocking on Maya's door in Santa Ynez. Sideways is a 127 minute drama/comedy film product by Michael London, directed by Alexander Payne and distributed by Fox Searchlight Pictures.