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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 119 wins & 78 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

Miles is a failed writer living a meager existence in San Diego as an English teacher. With his career seemingly fading and the fate of a book hinging on a publisher's decision, Miles is depressed with himself and what he hasn't achieved. Jack is a television actor whom some recognize but not many do, as if he were a minor actor who got a taste of success. With his best friend Miles, the two embark on a road trip through California's wine country. Miles wants to give his friend a nice sendoff before married life, while Jack simply wants to have a fling beforehand. As they're both nearing middle age with not much to show for it, the two will explore the vineyards while ultimately searching for their identities. Written by mystic80

Plot Summary | Plot Synopsis

Taglines:

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

Genres:

Comedy | Drama | Romance

Motion Picture Rating (MPAA)

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

Parents Guide:

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Details

Official Sites:

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Country:

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Language:

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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

Runtime:

Sound Mix:

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Color:

Aspect Ratio:

1.85 : 1
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Did You Know?

Trivia

According to W. Blake Gray of the San Francisco Chronicle, the producers had originally wanted to use a bottle of Petrus as the treasured wine gathering dust in Miles' apartment. But Christian Moueix, the chateau's owner, read the script and decided to pass. So, instead it was a bottle of 1961 Cheval Blanc. See more »

Goofs

When Miles pours the wine from the spit bucket at the tasting room over his head it drenches his shirt and pants. In the subsequent scenes, the wine stains have dried, but the clothes have actually been changed. There are stains on the shirt, but there are not enough to match the original incident and the pants have no stains at all. See more »

Quotes

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

Crazy Credits

Editorial Cat - Lulu See more »

Connections

Referenced in Suburban Knights (2011) See more »

Soundtracks

THURSDAY NIGHT AT PASQUALE'S
Written and Performed by Astrid Cowan
Courtesy of Astron Records
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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.


157 of 247 people found this review helpful.  Was this review helpful to you?

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Recent Posts
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
Greatest acting by an actor in a single Scene? the_wrinkled_mind
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