Sideways

Sideways
Theatrical release poster
Directed by	Alexander Payne
Produced by	Michael London
Screenplay by	Alexander Payne Jim Taylor
Based on	Sideways by Rex Pickett
Starring	Paul Giamatti Thomas Haden Church Virginia Madsen Sandra Oh
Music by	Rolfe Kent
Cinematography	Phedon Papamichael
Edited by	Kevin Tent
Production company	Michael London Productions
Distributed by	Fox Searchlight Pictures
Release date	September 13, 2004 (2004-09-13) (TIFF) October 22, 2004 (2004-10-22) (United States)
Running time	123 minutes
Country	United States
Language	English
Budget	$16 million
Box office	$109.7 million

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 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.

Payne and Taylor won multiple awards for their screenplay. The principal actors and actresses received accolades for their performances. Sideways won the Academy Award for Best Adapted Screenplay, and was nominated for four other awards including Best Picture. The film premiered at the 2004 Toronto International Film Festival on September 13, 2004 and was released in the United States on October 22, 2004.

As the film's cartoon poster suggests, the film is titled "Sideways" because, to age properly, wine bottles must be laid on their side; and similarly, anyone stuck in middle age must go "sideways in life" so as to change his ways and to grow as a person.

Miles Raymond is an aspiring – but unsuccessful – writer, a wine aficionado and a divorced, depressed, borderline alcoholic middle-aged English teacher living in San Diego, who takes his soon-to-be-married actor friend and former college roommate, Jack Cole, on a road trip through Santa Ynez Valley wine country. Though still recognized on occasion, Jack's acting career appears to have peaked years ago, when he had a role in a popular TV soap but now does commercial voice-overs and plans to enter his future father-in-law's successful real estate business after he's married. Miles wants to spend the week relaxing, golfing, 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.