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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.

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Won 1 Oscar. Another 120 wins & 82 nominations. See more awards »

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Cast

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

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

Taglines:

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


Motion Picture Rating (MPAA)

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

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Details

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Release Date:

21 January 2005 (USA)  »

Also Known As:

Entre copas  »

Box Office

Budget:

$12,000,000 (estimated)

Opening Weekend:

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

Gross:

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

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Technical Specs

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1.85 : 1
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Did You Know?

Trivia

Restaurant locations used in the Santa Ynez valley: Solvang Restaurant (breakfast scene before wine tasting); Los Olivos Cafe (dinner scene with Maya and Stephanie); AJ Spurs (dinner scene with Cammie); and of course The Hitching Post. See more »

Goofs

When Miles is driving to LA from San Diego one of the outside car shots shows long shadows as if the sun was setting when it is supposed to be mid afternoon. See more »

Quotes

[first lines]
Miles Raymond: Fuck.
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Crazy Credits

No California oak trees were harmed during the making of this production. See more »

Connections

Referenced in No Strings Attached (2011) See more »

Soundtracks

FADED AWAY
Written by Jamie Dunlap, Lisa Furr, and Scott Nickoley
Performed by Lisa Furr
Courtesy of Marc Ferrari/Mastersource
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Frequently Asked Questions

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User Reviews

A truly vintage comedy.
25 October 2004 | by (fairview, nj) – See all my reviews

SIDEWAYS (2004) **** Paul Giamatti, Thomas Haden Church, Virginia Madsen, Sandra Oh. (DIR: Alexander Payne)

A truly vintage comedy. Paul Giamatti is one of our finest character actors who seems to be neck-and-neck with William H. Macy on cornering the market of portraying losers as a cottage industry and in the latest endeavor of hapless misanthropes he may have found Oscar gold.

Giamatti stars as Miles Raymond, a miserable mope of a man who realizes he is never going to amount to anything especially given the fact that he is his own worst enemy in his highly critical outlook on life particularly on two things he holds dear: his struggling attempts to become a writer of notice and his taste in wine. The latter leads him to a certain road trip to salvation when he embarks upon a few days of r&r away from his stagnant day job as a middle school English teacher with his best friend and former college roomie Jack (Church in easily the career defining role of his life since his hey day on the TV sitcom 'Wings') whose impending nuptials is Miles' wedding gift as the best man. Jack, a long-in-the tooth second-rate soap actor whose 15 minutes are at a close 14:59 is adamant about getting laid for one last time before his commitment to a younger woman who clearly deserves better (and Jack shrewdly knows this).

As the duo drive through the sun-dappled wine country of Northern California in a road trip not unlike two virginal, horny teens looking to pop their respective cherries, they come across two unlikely conquests. One is the shapely and surprisingly-down-to-earth waitress Maya (Madsen in a career comeback of epic proportions shines through the Giamatti gloom) who strikes a fancy to the depressed Miles while Jack has his sights on the sexy wine pourer Stephanie (the sublimely, reassuringly funny Oh, and real – life wife to director Payne) who also is charmed by the blithely feckless Jack. What unfolds is a sweet yet too-good-to-be true few days of bliss and unbridled emotional rescue for the foursome as they take to one another like ducks to water although Miles' hesitancy is deeply reasoned since he is still licking the open wounds of his two-year old divorce.

Payne, one of my favorite filmmakers, doesn't disappoint as he dollops evenly the tragic-comic proceedings with his frequent long-time collaborator Jim Taylor in adapting an unpublished novel by Rex Pickett that has many layers to it and doesn't betray its four intriguing and ultimately human characters with all their flaws and neuroses on full display. Each actor shines with a few moments of soliloquies and dialogue that ring true that will have you laughing til you cry and vice versa (and that my friend is no easy trick)!

The four actors give supremely wonderfully acted turns and all are Oscar worthy as well as the screenplay which mixes misery with hope and some truly funny moments including an anger management golf sequence that feels like an outtake from 'Caddyshack' and Giamatti's drunken phone call to his ex is on par with Jon Favreau's car-accident-in-slow-motion answering machine mishap in 'Swingers' – one for the archives. Church makes his borderline jerk a quasi-pathetic lothario who finally sees the forest for the trees in a surprisingly moving moment of realization in a teary confessional; Oh unleashes the old chestnut of a woman's scorn with no-holds-barred and Madsen is a true welcome back from a seemingly endless string of nothing vehicles into this warm and welcome turn as comforting as a blanket on a wintry night in front of a cozy fire.

While it is so easy to resort to the wine as metaphor – as the film amply does with smart, sharp and pungent dialogue – the film is a full-bodied, never precocious vintage that needs to be savored in a desirable bouquet of cinematic finesse.


158 of 249 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
Do you think Jack and Miles are losers? This_is_an_outrage
Why are Miles and Jack even friends? pbaran
Miles and the cash in the Ajax bottle babybrotherandme
I did not get this movie. LifeMovieFan
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