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Sideways

Play trailer 2:24 Poster for Sideways R 2004 2h 6m Comedy Drama Mystery & Thriller Romance Play Trailer Watchlist
Watchlist Tomatometer Popcornmeter
97% Tomatometer 229 Reviews 79% Popcornmeter 100,000+ Ratings
Struggling writer and wine enthusiast Miles (Paul Giamatti) takes his engaged friend, Jack (Thomas Haden Church), on a trip to wine country for a last single-guy bonding experience. While Miles wants to relax and enjoy the wine, Jack is in search of a fling before his wedding. Soon Jack is sleeping with Stephanie (Sandra Oh), while her friend Maya (Virginia Madsen) connects with Miles. When Miles lets slip that Jack is getting married, both women are furious, sending the trip into disarray.
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Sideways

Sideways

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Critics Consensus

Charming, thoughtful, and often funny, Sideways is a decidedly mature road trip comedy full of excellent performances.

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Critics Reviews

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Anupama Chopra Film Companion May 18, 2020
This is a film about human beings who can be flawed and prickly but if you go a little deeper, you will see beauty. This is a wonderfully written script, with a great performance by Paul Giamatti. Go to Full Review Jonathan Rosenbaum Chicago Reader Feb 13, 2012
Payne does know how to capture two kinds of male menopause. But I can't say he ever surprised me. Go to Full Review Nell Minow Common Sense Media Dec 28, 2010
4/5
Excellent but explicit movie is not for kids. Go to Full Review Rachel Wagner Hallmarkies Podcast Apr 7, 2025
a solid film. Very well acted Go to Full Review Dan Buffa Ramble On With Buffa (Substack) Dec 29, 2024
My favorite scene in the film is an emotionally flattened Miles chowing down on a burger and fries while he pours a vintage bottle of wine into a Styrofoam cup while wearing a tux in a fast food shop. Giamatti made you feel all of it. Go to Full Review Allison Rose FlickDirect Oct 22, 2024
5/5
Giamatti, although overlooked by the Academy, serves as the emotional anchor of the film, holding its narrative together with his compelling performance. Go to Full Review Read all reviews

Audience Reviews

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Jacob W @RT17896586 1 day ago Struggling writer and wine enthusiast Miles (Paul Giamatti) takes his engaged friend, Jack (Thomas Haden Church), on a trip to wine country for a last single-guy bonding experience. While Miles wants to relax and enjoy the wine, Jack is in search of a fling before his wedding. Soon Jack is sleeping with Stephanie (Sandra Oh), while her friend Maya (Virginia Madsen) connects with Miles. When Miles lets slip that Jack is getting married, both women are furious, sending the trip into disarray. This is a brilliant film. Enjoy See more P C @Moviemonster94 Sep 2, 2026 A true love of mine. This movie is about as close to flawless as they come See more Christian K @ckacar Aug 7, 2026 F I need a big wine trip and also some nice wine to hold me over in the meantime. See more Thyaagu C @Thyaagu May 31, 2026 Funny, sad, and comforting all at once. Two men, one road trip, and a whole lot of bottled-up life. The kind of movie that doesn’t scream for attention but quietly wins you over scene by scene. See more z H. @Zorro925 Apr 17, 2026 Had me at: “I am not drinking any - - - - - - - merlot!” A classic. See more Jack F @MovieFan111 Apr 9, 2026 It was interesting I guess. Mature movie centered on adult mannerisms. I think the fact that it's considered to have aged like fine wine is really cool since that's a major theme in the movie itself. I liked the cast. See more Read all reviews
Sideways

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Cast & Crew

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Alexander Payne

Director

Paul Giamatti

Miles Raymond

Thomas Haden Church

Jack Lopate

Virginia Madsen

Maya

Sandra Oh

Stephanie

Marylouise Burke

Miles' Mother

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Sideways

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Sideways

From left: Paul Giamatti and Thomas Haden Church in SIDEWAYS From left: Paul Giamatti and Thomas Haden Church in SIDEWAYS From left: Paul Giamatti and Thomas Haden Church in SIDEWAYS From left: Sandra Oh, Thomas Haden Church, Virginia Madsen and Paul Giamatti in SIDEWAYS From left: Thomas Haden Church and Paul Giamatti in SIDEWAYS From left: Paul Giamatti and Virginia Madsen in SIDEWAYS From left: Paul Giamatti, Virginia Madsen, Director Alexander Payne, Thomas Haden Church and Sandra Oh on the set of SIDEWAYS From left: Paul Giamatti and Thomas Haden Church in SIDEWAYS From left: Sandra Oh and Thomas Haden Church in SIDEWAYS From left: Virginia Madsen, Paul Giamatti, Thomas Haden Church and Sandra Oh in SIDEWAYS View more photos

Movie Info

Synopsis Struggling writer and wine enthusiast Miles (Paul Giamatti) takes his engaged friend, Jack (Thomas Haden Church), on a trip to wine country for a last single-guy bonding experience. While Miles wants to relax and enjoy the wine, Jack is in search of a fling before his wedding. Soon Jack is sleeping with Stephanie (Sandra Oh), while her friend Maya (Virginia Madsen) connects with Miles. When Miles lets slip that Jack is getting married, both women are furious, sending the trip into disarray.
Director
Alexander Payne
Producer
Michael London, George Parra
Screenwriter
Rex Pickett, Alexander Payne
Distributor
Fox
Production Co
Fox Searchlight, Michael London Productions
Rating
R (Nudity|Language|Some Strong Sexual Content)
Genre
Comedy, Drama, Mystery & Thriller, Romance
Original Language
English
Release Date (Theaters)
Oct 22, 2004, Original
Release Date (Streaming)
Sep 2, 2014
Box Office (Gross USA)
$71.5M
Runtime
2h 6m
Sound Mix
Surround, Dolby SRD
Aspect Ratio
Flat (1.37:1)
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