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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?


A reporter asked Alexander Payne if Miles running down the grassy hill was purposely evoking the opening credits to Little House on the Prairie (1974). It was actually borrowed, with permission, from the thesis film of one of Payne's former classmates. See more »


In the scene where Jack tells Miles he thinks he's in love with Stephanie, Miles's arms are crossed over, then his fingers are laced together in the next shot, then his arms are crossed over again two shots later. See more »


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

Crazy Credits

Editorial Cat - Lulu See more »


References One Life to Live (1968) See more »


Written and Performed by Uli Lenz
Courtesy of Arkadia Entertainment Corp.
By Arrangement with Position Music
See more »

Frequently Asked Questions

See more (Spoiler Alert!) »

User Reviews

Morally Bankrupt? Call me!
20 November 2004 | by (Los Angeles, CA) – See all my reviews

My girlfriend is lucky enough to be on the Screen Actor Guild Awards nominating committee this year, so the promotional DVDs are flowing in, and SIDEWAYS is absolutely the best film we've seen so far. (Kinsey is a close second.) Paul Giamatti should get a nomination for this, and I want people on IMDb to start understanding that when you critique a film, it's not ALL about liking the character-- one IMDBer commenting on this film trashed Sideways because she thought the characters were morally bankrupt, and I challenge all of you to show me a good movie where the main characters aren't! That's how the necessary element of conflict is created in a story!

Can you really only enjoy films where the characters in them are people you'd have over for dinner? OPEN YOUR MINDS! Feature Films are not popularity contests, and as far as I'm concerned, neither are awards competitions. Giamatti steals cash from his mother's bedroom dresser drawer near the beginning of the film. Morally reprehensible? Absolutely! But my heart broke for him when he did it. You could see how much he hated himself in that moment!!! Giamatti's ability to have intensely personal thoughts flash through his eyes like flickering film through a projector, all the while maintaining such beautiful stillness, was for me breathtaking. Giamatti makes you completely suspend your disbelief...he makes you feel like you have ESP!!!

Thomas Hayden Church was hilarious as his ex-college roommate/infantile thirtysomething playboy buddy who can't let go of "his plight." He's a stitch. And I agree with everyone, Virgina Madsen makes you melt in this film. She is scrumptuous. Remember, IMDb moralists,...people who live in glass movie-houses, shouldn't throw popcorn! ~peace

278 of 421 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
Why are Miles and Jack even friends? pbaran
Do you think Jack and Miles are losers? This_is_an_outrage
I did not get this movie. LifeMovieFan
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