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Sideways (2004)

126 min · Road Movie, Romantic Comedy, buddy film, comedy drama, drama film, romantic comedy film

Popularity5/5
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12-month trend

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32k02025-09: 23,342 views2025-10: 22,391 views2025-11: 23,804 views2025-12: 32,403 views2026-01: 32,107 views2026-02: 19,490 views2026-03: 22,381 views2026-04: 20,544 views2026-05: 23,529 views2026-06: 20,451 views2026-07: 21,722 views2026-08: 32,073 views
Sep23kOct22kNov24kDec32kJan32kFeb19kMar22kApr21kMay24kJun20kJul22kAug32k

2025-09 to 2026-08

Two men on a road trip to wine country before a wedding navigate their personal failures and the complexities of their friendship.

The story

Sideways follows two men in their forties, Miles Raymond, a depressed teacher and unsuccessful writer, and Jack Cole, a past-his-prime actor, who embark on a week-long road trip to Santa Barbara County wine country. The journey is intended to celebrate Jack's upcoming wedding. While Miles seeks to relax and enjoy the local wine and food, Jack is determined to help Miles overcome his professional failures and personal struggles. As they travel through the Santa Ynez valley, the pair navigates their differing expectations for the trip, their complicated personal lives, and the complexities of their long-standing friendship amidst the scenic backdrop of California's wine country.

Full plot (contains spoilers)

Miles Raymond, a struggling writer and teacher, and his friend Jack Cole, a struggling actor, travel to Santa Barbara County to celebrate Jack's upcoming wedding. Miles steals money from his mother before they leave. During the trip, Miles teaches Jack about wine in the Santa Ynez valley. Jack attempts to find a sex partner for Miles, leading to a double date with a woman named Stephanie. After a series of complications involving a woman named Maya and a dishonest lie about Miles' manuscript, the men face various mishaps. Jack's lies about his feelings for Stephanie lead to a physical altercation, and a subsequent tryst with a woman named Cammi results in Jack being chased by her husband. After a staged car accident to cover his lies, they attend the wedding. Miles eventually receives a message from Maya and returns to wine country to visit her.

First release year
2004
Runtime (minutes)
127
Production countries
United States
Original languages
English
Directors
Alexander Payne
Writers
Alexander Payne · screenplay; Jim Taylor · screenplay
Cast and characters
Paul Giamatti · Miles Raymond; Thomas Haden Church · Jack Cole; Virginia Madsen · not specified; Sandra Oh · not specified
Genres
comedy-drama; black comedy; independent; romantic comedy-drama
Themes
friendship; midlife crisis; alcoholism; failure
Tone and mood
comedy; drama
Premise and plot tags
road trip; buddy comedy; wine culture
Source material / true-story basis
Rex Pickett's 2004 novel, Sideways
Content notes
alcoholism
Reception
The film received widespread acclaim from critics and is regarded as one of the greatest films of the 2000s. It was described as 'intelligent, funny and moving' and 'the best human comedy of the year'.
Reported review scores
Rotten Tomatoes · score: 97% · scale: percentage · review count: 230; Metacritic · score: 94 · scale: 100 · review count: 42; CinemaScore · score: B · scale: A+ to F
Awards and nominations
Academy Award · Best Adapted Screenplay · won; Academy Award · Best Picture · nominated; Academy Award · Best Director · nominated; Academy Award · Best Supporting Actor · nominated; Academy Award · Best Supporting Actress · nominated; Independent Spirit Award · Best Supporting Actor · won; Independent Spirit Award · Best Supporting Actress · won
Catalogue themes and tags

Actress, Autorin, Bachelor party, California, Golf, Man-Woman-Relationship, Tour, Trinken, Wedding Vows, Wine, romanze, Romantic comedy, Buddy film, Road movie, Comedy-drama, Drama, Comedy, Romance Film

Film metadata comes from the open sources listed in Credits & Contact. Catalogue details may be incomplete.

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