Sideways

***Sideways*** is a 2004 American independent black comedy drama film.

## Synopsis

Two men reaching middle age with not much to show but disappointment embark on a week-long road trip through California's wine country, just as one is about to take a trip down the aisle.

## Plot

Miles Raymond is an aspiring, 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 Valleywine country. Though he is still recognized on occasion, Jack's acting career appears to have peaked years ago, when he had a role in a popular TV soap. He now does commercial voice-overs and plans to enter his future father-in-law's successful real estate business. 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.

In the wine country, the pair visit Miles' favorite restaurant, The Hitching Post II, and encounter Maya, an attractive, intelligent waitress with whom Miles is casually acquainted. Jack senses that Maya is interested in Miles, who believes she is married. Jack lies to Maya that Miles' manuscript has been accepted for publication, even though it is only being considered. At a tasting in a local winery, Jack and Miles meet an attractive wine pourer named Stephanie, who is also acquainted with Maya. Jack is immediately attracted to Stephanie and arranges a double date, having discovered Maya is no longer married ("sans rock", as he describes it).

During the date, Miles gets drunk and telephones Vicki, his ex-wife, after learning from Jack that she has remarried. They go to Stephanie's home, where she and Jack immediately adjourn to her bedroom for sex. Miles and Maya connect through their mutual interest in wine. Maya says she is finishing a master's degree in horticulture so she can leave serving. They leave separately, but not before Miles gives her a copy of his manuscript.

Jack's affair with Stephanie continues, to the point where he believes he's falling in love; he bonds with her daughter and suggests to Miles that they move here for him to be closer to Stephanie, calling off his wedding. After spending a day together, Miles and Maya return to her apartment and have sex. The next morning, Miles lets it slip that Jack is to be married. Disgusted with the dishonesty, Maya dumps Miles and tells Stephanie, who, furious and devastated that she's been used, breaks Jack's nose using her motorcycle helmet.

On finding out his manuscript has been rejected again, Miles drinks heavily. When a server cuts him off, he ends up drinking from the spit bucket, creating a scene. That night, Jack hooks up with another waitress named Cammi, who recognizes him from his acting career. Hours later, Jack shows up at the motel  – naked and confessing that Cammi's husband came home while she and Jack were having sex. Jack was forced to flee without his clothes and wallet (which contains a pair of irreplaceable wedding rings). He convinces Miles to sneak into the house, where he discovers Cammi and her husband having sex. Miles grabs the wallet and runs, barely escaping Cammi's irate husband, who pursues him in the nude. To explain the broken nose to his fiancée, Jack runs Miles' Saab 900 convertible into a tree, giving the appearance they had been in an accident. The pair return to the fiancée's home, where Jack is welcomed with open arms. Miles meanwhile drives away in his battered car.

Following the wedding ceremony, Miles runs into his ex-wife Vicki and meets her new husband. Learning that she is also pregnant, Miles's depression hits rock bottom. Alone, he drinks his prized wine, a 1961 *Château Cheval Blanc*, from a disposable styrofoam soda cup at a fast-food restaurant. Time passes as Miles returns to the routine of teaching school, until one day he receives a voice-mail from Maya, who says she enjoyed his manuscript and invites him to visit. Miles is seen driving back to wine country and knocking on Maya's door.

## Adapatations

### Novel trilogy

Later on, this film was adapated into a novel trilogy:

1. *Sideways* (2004)
2. *Vertical* (2010)
3. *Sideways 3 Chile* (2015)

### Musical

In 2019, it was announced that *Sideways* was scheduled to adapted for a Broadway musical. A play adapted by author Rex Pickett from the Sideways novel was produced at multiple theaters in the United States and the United Kingdom, including at the La Jolla Playhouse.

### Stage

In addition to the musical, it was reported that Rex Pickett had written screenplays based on his two Sideways sequels already in print, *Vertical* and *Sideways 3 Chile*.