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Sideways (2004)

R  |   |  Comedy, Drama, Romance  |  21 January 2005 (USA)
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Ratings: 7.6/10 from 141,404 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?


This is the first film to win best screenplay from all five "major" critic groups (National Board Of Review, New York, Los Angeles, Brodcast and National Society Critics), the Golden Globes, the WGA and, ultimately, the Academy Awards. See more »


Miles drops off Jack in front of Christine's house. You see them unload the golf clubs and wine boxes on the left side of the porch, close to the door. In the next scene you see Miles in the car observing Jack who knocks on the door. It appears that the golf clubs and boxes of wine are not in the scene when Jack knocks and the door is opened by Christine. At the end of the scene the boxes and clubs can be seen to the far right side of the porch, further away from the door. See more »


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

Crazy Credits

Editorial Cat - Lulu See more »


Referenced in Albatross (2015) 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

If anyone orders Merlot, I'm leaving
14 November 2004 | by (Dallas, Texas) – See all my reviews

Greetings again from the darkness. Writer/Director Alexander Payne was the creative force behind one of my favorite films from the past couple of years with "About Schmidt". With "Sideways" he proves his insight into human nature was no fluke, but instead, an amazing gift. He captures many Hollywood stereotypes such as mid-life crisis, groom-to-be cold feet, post-divorce confidence crunch and the overall desire to be loved, or at least liked. What makes Payne's work so unique is his ability to deliver multiple messages, with brilliant comic twists, using little more than unlikeable lead characters and sizzling dialogue! Moral bankruptcy is at a peak in "Sideways" as one of our leads (the magnificent Paul Giamatti from "American Splendor" and "Man on the Moon") steals cash from his mother and the other (Thomas Haden Church from TV's "Wings") is on a mission to have his bachelor party last an entire week while claiming we just don't understand his plight. Also delivering a wonderful touch to the film is Sandra Oh (Diane Lane's pregnant buddy in "Under the Tuscan Sun"). Oh has very unique looks and mannerisms, but is terrific as one of Church's conquests. The soul and spirit of this film belongs to the drastically underrated Virginia Madsen (if you have never seen "The Hot Spot", make it priority viewing). Madsen (sister to cult favorite Michael Madsen of "Kill Bill" and "Reservoir Dogs" fame) literally jumps off the screen with her eyes and smile. Her character wants so much for a better life, but is strong enough to avoid her past mistakes. She is the one we root for. This is an excellent film and nice character study with a snappy jazz score. Payne has proved he should be considered among the best filmmakers of today - now could someone please help his film obtain better distribution!!!

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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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