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Sideways (2004)

R  |   |  Comedy, Drama, Romance  |  21 January 2005 (USA)
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Ratings: 7.6/10 from 141,377 users   Metascore: 94/100
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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 »
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Won 1 Oscar. Another 133 wins & 52 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


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


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?


Sandra Oh learned how to ride a motorcycle for her part in this film. See more »


Miles unwraps the bunch of money he finds in his mother's drawer.In the next shot it is clear that the currencies he is holding were never wrapped. See more »


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

Crazy Credits

Editorial Cat - Lulu See more »


Features The Grind (1992) See more »


Written by Dillon O'Brian
Performed by Bonnie Raitt
Courtesy of Capitol Records
Under license from EMI Film & Television Music
See more »

Frequently Asked Questions

See more (Spoiler Alert!) »

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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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
I did not get this movie. LifeMovieFan
One of my favourite movies, ever! wisperingdeth
Greatest acting by an actor in a single Scene? the_wrinkled_mind
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