Miles Raymond picks up his friend Jack Cole at the home of Cole’s fiancée to begin a week together in advance of Cole’s wedding. Miles, a school teacher and unpublished author, starts the trip at his mother’s house, ostensibly to wish her a happy birthday, but Miles steals money before they leave.
Miles wants to spend the week relaxing, playing golf, and enjoying good food and wine. However, Jack is interested in trying to cure Miles’ depression over his professional failures and divorce by finding him a sex partner. Jack is ambivalent over his pending marriage and the prospect of giving up his acting ambitions in favor of a job with his fiancée’s father. In the Santa Ynez valley, Miles, anoenophile, teaches Jack how to taste wine. The pair dine atThe Hitching Post II. Jack infers that Maya, a waitress with whom Miles is casually acquainted, is interested in Miles. Jack tells Maya that Miles' manuscript has been accepted for publication, although it is only being considered.
The next morning Jack announces his intention to find sex partners during the trip. That night, he arranges a double date for himself and Miles with a wine pourer named Stephanie, who is also acquainted with Maya.
During the date, Miles getsdrunk and telephones Victoria, his ex-wife, after learning from Jack that she has remarried and will be bringing her new husband to Jack's wedding. The couples go to Stephanie's house, where Stephanie and Jack adjourn to Stephanie's bedroom, leaving Miles and Maya alone. The two connect through their mutual interest in wine, and- after hearing Jack and Stephanie having sex through the wall- Miles kisses Maya awkwardly. As they part, Miles gives Maya a copy of his manuscript, which she had earlier expressed interest in reading.
Jack claims to have fallen in love with Stephanie and tells Miles he wants to postpone the wedding and move to the Santa Ynez Valley to be closer to her. After spending time with Jack and Stephanie at wineries and a picnic, Miles and Maya return to Maya's apartment and have sex. The next day, Miles reveals to Maya that Jack is getting married. Disgusted with the men's dishonesty, Maya dumps Miles.
Jack and Miles go to a winery that Miles finds subpar. After hearing from his literary agent that his manuscript has been rejected, an upset Miles pesters the pourer for a full glass of wine. When the server refuses, Miles drinks from thespit bucket, creating a scene. Jack intervenes and drives Miles back to the motel. Upon arrival, Stephanie, who heard from Maya about Jack's marital status, furiously beats Jack with her motorcycle helmet, breaking his nose, while berating him for his dishonesty. Miles takes Jack to theER and leaves Maya an apologetic voice message, admitting that his book will not be published.
That night, despite Miles' protests, Jack goes home with a waitress named Cammi. Jack returns to the motel naked after Cammi's husband had caught the two having sex. Jack begs Miles to help him retrieve his wallet, which contains custom wedding rings. Miles sneaks into the house, where he finds Cammi and her husband having sex. He grabs the wallet and runs, barely escaping Cammi's nude and furious husband. On the drive back to San Diego, Jack intentionally drives Miles's car into a tree to support hisalibi that he broke his nose in a car accident. The pair return to Christine's home, where Jack is warmly received by her family.
Following the wedding ceremony, Miles runs into Victoria and meets her new husband, Ken. Victoria says she is pregnant. Miles absconds before the reception and drives back to his San Diego apartment. Alone, he drinks his prized wine, a 1961Château Cheval Blanc, from a disposable styrofoam soda cup at afast-food restaurant. One day, Miles receives a voicemail from Maya, saying she loved his manuscript, encouraging him to keep writing, and inviting him to visit. Miles drives back to wine country and knocks on Maya's door.
A 2009 study bySonoma State University found thatSideways slowed the growth in Merlot sales volume and caused its price to fall, but the film's main effect on the U.S. wine industry was a rise in the sales volume and price of Pinot noir and in overall wine consumption.[9]
A 2022 study in theJournal of Wine Economics found thatSideways caused a reduction in demand for Merlot and an increase in demand for Pinot noir in the United States, which led California winemakers to grow Pinot noir grapes in unsuitable land and blend those grapes with the grapes grown in high-quality areas just to meet demand, which may have led to worse Pinot noir wines.[10][11]
Sideways Fest is an annual 3-day event hosted by the Sta. Rita Hills Wine Alliance celebrating the movie's release featuring the local viticulture and scenery.[12]
In 2013,Rex Pickett, author of theSideways novel, released his own Pinot noir named Le Plus Ultra.[13] In 2020, he released a Pinot noir named Sideways.[14]
The originalsoundtrack album features 15jazzinstrumentals composed and produced byRolfe Kent and was orchestrated and arranged for the band byTony Blondal. The album was nominated for theGolden 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 fromSymbiosis byClaus Ogerman andBill Evans.
Onreview aggregatorRotten Tomatoes,Sideways has an approval rating of 97% based on 233 reviews, and an average rating of 8.5/10. The website's critical consensus reads: "Charming, thoughtful, and often funny,Sideways is a decidedly mature road trip comedy full of excellent performances."[15] OnMetacritic, the film has aweighted average score of 94 out of 100 based on 42 reviews, indicating "universal acclaim".[16] Audiences polled byCinemaScore gave the film an average grade of "B" on an A+ to F scale.[17]
Time Out described the film as "intelligent, funny and moving",[18] andRoger Ebert of theChicago Sun-Times gave it 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".[19]
Sideways was ranked 494th onEmpire's 2008 list of the 500 greatest movies of all time.[21]Total Film putSideways on its list of 100 Greatest Movies of All Time.[22] In 2013, theWriters Guild of America also ranked its script as the 90th greatest ever written.[23] The February 2020 issue ofNew York Magazine listsSideways as among "The Best Movies That Lost Best Picture at the Oscars."[24] In 2025, it was one of the films voted for the "Readers' Choice" edition ofThe New York Times' list of "The 100 Best Movies of the 21st Century," finishing at number 173.[25]
In 2019, it was announced thatSideways was scheduled to be adapted for a stage musical.[26]Kathleen Marshall is expected to be the director and choreographer for the musical, which was aiming for a spring or summer 2020 tryout in a regional venue prior toBroadway. The musical will have a book byRex Pickett and the score by Anthony Leigh Adams.[27]
A play adapted by author Rex Pickett from theSideways novel was produced at multiple theaters in the United States and the United Kingdom, including at theLa Jolla Playhouse.[26]
In addition to the musical, it was reported that Pickett had written screenplays based on his twoSideways sequels already in print,Vertical andSideways 3 Chile.[26]
The remake shifts the setting of the film toNapa Valley. Although listed as an executive producer, Payne was not involved with the remake, although he gave it his blessing.[61] Giamatti declined an invitation to make an unspecifiedcameo appearance in the film.[62]
Pickett has written three sequel books toSideways, the second of which beingVertical (2010) which follows Miles and Jack on a road trip to Oregon with Miles' mother.Fox Searchlight retains the film rights to the characters, but Payne has expressed disinterest in directing a sequel toSideways, and no further adaptations have been made.[63]
^"2004 Awards (8th Annual)".Online Film Critics Society. January 3, 2012.Archived from the original on January 21, 2013. RetrievedFebruary 10, 2023.
^King, Susan (January 6, 2005)."Producers' '04 nominees".Los Angeles Times.Archived from the original on September 21, 2015. RetrievedFebruary 10, 2023.
