Sideways

Miles Raymond is an unsuccessful writer, a wine aficionado, and a divorced and depressed middle-aged English teacher living in San Diego. He takes Jack Cole, his soon-to-be-married actor friend and former college roommate, on a road trip through the Santa Ynez Valley wine country. At the beginning of this trip, he stops to see his mother before the day of her birthday. While there he steals a thousand dollars from her secret stash. Though Jack is still recognized on occasion, his acting career appears to have peaked years earlier, 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, playing golf and 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, a 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. As they are walking back to the motel, Jack tells Miles that Maya did not have a wedding ring on at the bar, implying that she is single as he suspected. At a tasting in a local winery, Jack and Miles meet a wine pourer named Stephanie, who is also acquainted with Maya. Jack is immediately attracted to Stephanie and arranges a double date.

During the date, Miles gets drunk and telephones Victoria, his ex-wife, after learning from Jack that she has remarried. The two couples go to Stephanie's home, where she and Jack adjourn to her bedroom for sex. Miles and Maya connect through their mutual interest in wine. While in Stephanie's kitchen, Miles awkwardly attempts to kiss her. As they are leaving separately, Miles gives her a copy of his manuscript, which Maya had earlier expressed interest in reading.

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 a disgusted Miles that they move there for him to be closer to Stephanie. After spending time with Jack and Stephanie at wineries and a picnic, Miles and Maya return to her apartment and have sex. The next day, after spending time with her in town, Miles lets it slip that Jack is to be married. Disgusted with the men's dishonesty, Maya dumps Miles.

Jack and Miles go to a winery that Miles immediately calls mediocre. After receiving word from his literary agent that his manuscript has been rejected, an upset Miles tries to get the server to give him a "full pour" of wine. When the server refuses, Miles ends up drinking from the spit bucket in the tasting room, creating a scene. Jack intervenes and drives Miles back to the motel. Upon arrival, they meet Stephanie, who hits Jack in the face with her motorcycle helmet, screaming about his impending wedding and his supposed love for her. Miles takes Jack to the ER and leaves Maya an apologetic voice message, admitting that his book is not going to be published. That night, Jack hooks up with a waitress named Cammi, much to Miles' disgust. 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 the irate husband, who pursues him in the nude.

To explain his broken nose to his fiancée, Jack intentionally damages Miles' Saab 900 convertible, 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 drives away in his battered car.

Following the wedding ceremony, Miles runs into his ex-wife Victoria and meets her new husband. Victoria tells Miles that she is pregnant. Alone, Miles 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. One day he receives a voicemail from Maya, who says she enjoyed his manuscript and invites him to visit while warning that she may soon relocate. Miles drives back to wine country and knocks on Maya's door.

The Hitching Post II Restaurant in Buellton where Miles and Jack first encounter Maya.

The film drew attention and increased tourism to the Santa Ynez Valley wine-growing region of California's Central Coast. Throughout the film, Miles speaks fondly of the red wine varietal Pinot Noir while denigrating Merlot.[2][3] Following the film's U.S. release in October 2004, Merlot sales dropped 2% while Pinot Noir sales increased 16% in the Western United States. A similar trend occurred in British wine outlets.[3][4][5][6][7][8]

A 2009 study by Sonoma State University found that Sideways slowed the growth in Merlot sales volume and caused its price to fall, but the film's main effect on the wine industry was a rise in the sales volume and price of Pinot Noir and in overall wine consumption.[9]

The original soundtrack album features 15 jazz instrumentals composed and produced by Rolfe Kent and was orchestrated and arranged for the band by Tony Blondal. The album was nominated for the Golden Globe Award for "Best Original Score", and the music proved so popular there was demand for a national tour. Eventually a few cities were chosen to perform in as the composer was too busy to commit to more. The romantic leitmotif shared by Miles and Maya is excerpted from Symbiosis by Claus Ogerman and Bill Evans.

1. "Asphalt Groovin'" – 4:00
2. "Constantine Snaps His Fingers" – 3:03
3. "Drive!" – 3:56
4. "Picnic" – 2:15
5. "Lonely Day" – 1:40
6. "Wine Safari" – 2:13
7. "Miles' Theme" – 2:59
8. "Los Olivos" – 2:43
9. "Chasing the Golfers" – 3:03
10. "Walk to Hitching Post" – 2:32
11. "Abandoning the Wedding" – 3:25
12. "Slipping Away As Mum Sleeps" – 1:00
13. "Bowling Tango" – 0:49
14. "I'm Not Drinking Any #@%!$ Merlot!" – 1:13
15. "Miles And Maya" – 2:26

On review aggregator Rotten Tomatoes, the film has an approval rating of 97% based on 233 reviews and an average score of 8.55/10. The website's critical consensus reads: "Charming, thoughtful, and often funny, Sideways is a decidedly mature road trip comedy full of excellent performances."[10] On Metacritic, the film has a score of 94 out of 100, based on 42 reviews, indicating "universal acclaim".[11] Audiences polled by CinemaScore gave the film a "B" grade on an A+ to F scale.[12]

Time Out described the film as "intelligent, funny and moving",[13] and Roger Ebert of the Chicago Sun-Times gave the film four stars out of four, writing that,"what happens during the seven days adds up to the best human comedy of the year – comedy, because it is funny, and human, because it is surprisingly moving."[14] A surprise hit, Sideways became popular in Hollywood, the US, and internationally. Santa Ynez Valley, where much of the film is set, experienced increased tourism. The film was nominated for dozens of awards, winning many, and was dubbed "the best reviewed movie of 2004."

With the exception of Giamatti, who had already starred in the critically acclaimed film American Splendor, the film was a career breakthrough for the stars. Church and Madsen were each nominated for the Screen Actors Guild Award, Golden Globe Award, and Academy Award for their performances, winning the Broadcast Film Critics Association Award and Independent Spirit Award for their respective categories. Giamatti has since been headlined as "The World's Best Character Actor" by Time magazine.[15] Sandra Oh went on to star in the ABC medical drama Grey's Anatomy, for which she won two Screen Actors Guild Awards and one Golden Globe Award.

Sideways was ranked 494th on Empire's 2008 list of the 500 greatest movies of all time.[16] Total Film put Sideways on its list of 100 Greatest Movies of All Time.[17] In 2013, the Writers Guild of America also ranked its script as the 90th greatest ever written.[18]

In 2019, it was announced that Sideways was scheduled to be adapted for a stage musical.[19] Kathleen Marshall is expected to be the director and choreographer for the musical, which is aiming for a spring or summer 2020 tryout in a regional venue prior to Broadway. The musical will have a book by Rex Pickett and the score by Anthony Leigh Adams.[20]

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.[19]

In addition to the musical, it was reported that Pickett had written screenplays based on his two Sideways sequels already in print, Vertical and Sideways 3 Chile.[19]

Fox International Productions and Fuji TV released a Japanese-language remake of the film in October 2009,[21] often rendered in Romaji as Saidoweizu. The film is directed by Cellin Gluck and stars Katsuhisa Namase, Fumiyo Kohinata, Kyōka Suzuki, and Rinko Kikuchi, and has a soundtrack composed and performed by Hawaiian-born ukulele virtuoso Jake Shimabukuro.

The remake shifts the setting of the film to Napa Valley. Although listed as an executive producer, Payne was not involved with the remake, although he gave it his blessing.[22] Giamatti declined an invitation to appear in an unspecified cameo appearance in the film.[23]

Pickett wrote a sequel to his novel, Vertical, in 2011, following Miles and Jack on a road trip to Oregon with Miles' mother. However, Payne has declined to consider a sequel to the film. Fox Searchlight owns the rights to the characters, but Payne's lack of interest makes the film a non-starter for Fox.[24]

• List of American films of 2004
• Second weekend in box office performance § Second-weekend increase

• Sideways at IMDb
• Sideways at AllMovie
• Sideways review by Roger Ebert
• The Danish Soul of That Town in Sideways