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Two men reaching middle age with not much to show but disappointment embark on a week-long road trip through California's wine country, just as one is about to take a trip down the aisle.



(novel), (screenplay) | 1 more credit »
2,069 ( 78)
Won 1 Oscar. Another 120 wins & 82 nominations. See more awards »



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Cast overview, first billed only:
Mrs. Erganian (as Shaké Toukhmanian)
Mike Erganian (as Duke Moosekian)
Miles's Building Manager
Gary the Bartender
Stephanie's Mother
Frass Canyon Pourer


A week before his friend Jack is to be married, best man Miles and the prospective groom head off to wine country for a week of fun, relaxation and - of course - wine drinking. Miles is the oenophile and does his best to teach Jack a bit about the art of appreciating great wine. All Jack cares about is drinking and carousing, something he accomplishes when he meets the attractive Stephanie at one of the vineyards. Miles is something of a sad sack, a high school English teacher who is a failed writer at heart. He has yet to get over the fact that his wife has divorced him and that she has remarried and he now faces that nerve racking wait for word from a prospective publisher. Miles has an opportunity to start anew when he meets Stephanie's friend Maya but when he let's slip that Jack is about to be married any hope of a relationship seems to be lost. Written by garykmcd

Plot Summary | Plot Synopsis


In search of wine. In search of women. In search of themselves.


Comedy | Drama | Romance

Motion Picture Rating (MPAA)

Rated R for language, some strong sexual content and nudity | See all certifications »

Parents Guide:



Official Sites:






Release Date:

21 January 2005 (USA)  »

Also Known As:

Entre copas  »

Box Office


$12,000,000 (estimated)

Opening Weekend:

$207,042 (USA) (22 October 2004)


$71,502,303 (USA) (13 May 2005)

Company Credits

Show detailed on  »

Technical Specs


Sound Mix:



Aspect Ratio:

1.85 : 1
See  »

Did You Know?


Rex Pickett later produced a sequel in novel form named "Vertical", in which Miles writes a best seller and is again reunited with his mother and Jack. However according to Pickett, Alexander Payne had no interest in directing a film version of sequel. See more »


Maya and Miles are picnicking on the blanket and Miles is engrossed in his crossword puzzle. #52 across clue is "Corroborated" and Miles has written in "Workedwine" instead of "workedwith". See more »


[first lines]
Miles Raymond: Fuck.
See more »

Crazy Credits

Editorial Cat - Lulu See more »


Referenced in Alexander Payne Introduction to 'Il Sorpasso' (2014) See more »


Words and Music by David Klingenberger (as David Allen Klingenberger) and Edward M. Rudolph
Performed by Deke Dickerson
Courtesy of Songs of D.K.
See more »

Frequently Asked Questions

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User Reviews

Giamatti was ROBBED!
25 January 2005 | by (New York) – See all my reviews

Sideways is a beautiful portrait of mid life disappointment. The backdrop is lovely California wine country, and the casting is flawless. Every single performance in this film is surprising, pitch perfect, and unusual. The movie has the remarkable ability to capture sadness and desperation in just the light that allows the audience to recognize the humor. The ending is satisfying but not too pat. In short, this is the best film of 2004.

The standout performance in the film was Paul Giamatti's. I cannot believe he was passed over for an Oscar this year. He should have been nominated for American Splendor, and he definitely should have been nominated for Sideways. His performance was beautiful, romantic, heartbreaking and so human. Paul Giamatti, ignore the Academy! Every year they have less credibility. The people who know films and acting at all know that you are one in a handful of truly great actors working in Hollywood today.

385 of 549 people found this review helpful.  Was this review helpful to you?

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One of the most overrated movies of all-time Johnboy1221
Is Maya Too Good For Miles? Onyx12
Miles and the cash in the Ajax bottle babybrotherandme
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I did not get this movie. LifeMovieFan
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