A film adaptation of Rex Pickett's 2004 novel, 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.

Jack is ambivalent over his pending marriage and the prospect of giving up his acting ambitions in favor of a job with his fiance's father.

That night, he arranges a double date for himself and Miles with a wine pourer named Stephanie, who is also acquainted with Maya.

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 hearing from his literary agent that his manuscript has been rejected, an upset Miles pesters the pourer for a full glass of wine.

Miles takes Jack to the ER and leaves Maya an apologetic voice message, admitting that his book will not be published.

Alone, he drinks his prized wine, a 1961 Château Cheval Blanc, from a disposable styrofoam soda cup at a fast-food restaurant.

One day, after coming home from his teaching job, Miles receives a voicemail from Maya, saying she loved his manuscript, encouraging him to keep writing, and inviting him to visit.

Wineries and locations in the Santa Ynez Valley are prominently featured in the film, drawing attention and increased tourism to the Sta.

[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 U.S. wine industry was a rise in the sales volume and price of Pinot noir and in overall wine consumption.

[14] 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.

The website's critical consensus reads: "Charming, thoughtful, and often funny, Sideways is a decidedly mature road trip comedy full of excellent performances.

[24] 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 to Broadway.

Fox International Productions and Fuji TV released a Japanese-language remake of the film in October 2009,[58] サイドウェイズ, 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.

Fox Searchlight retain the film rights to the characters, but Payne has expressed disinterest in directing a sequel to Sideways, and no further adaptations have been made.