Sideways

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2:24

Sideways

R

2004

2h 6m

Comedy

Drama

Mystery & Thriller

Romance

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Tomatometer

Popcornmeter

96%

Tomatometer

225 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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Critics Consensus

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

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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.

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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.

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Nell Minow

Common Sense Media

Dec 28, 2010

4/5

Excellent but explicit movie is not for kids.

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Rachel Wagner

Hallmarkies Podcast

Apr 7, 2025

a solid film. Very well acted

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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.

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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.

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Jacob W

@RT17896586 Oct 24, 2026

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

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P C

@Moviemonster94 Sep 2, 2026

A true love of mine. This movie is about as close to flawless as they come

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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.

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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.

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z H.

@Zorro925 Apr 17, 2026

Had me at: “I am not drinking any - - - - - - - merlot!” A classic.

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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.

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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

Cousin Bette

45%

44%

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Sideways: Trailer 1

2:24

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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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