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Sideways (Widescreen Edition) (2005)

A movie directed by Alexander Payne

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A Midlife Crisis Uncorked

  • Jan 2, 2009

Director Alexander Payne (Election and About Schmidt) creates a mature, masterfully crafted comedy with his film Sideways. The film is rich in characterization and features stunning performances by its talented cast. When the film was released in 2004, it garnered critical praise and numerous award nominations. But all the hype aside, Sideways is a surprisingly engaging and intelligent comedy about two self-centered men, who learn that they need to grow up.

Drinking too much... 


Miles, a recovering alcoholic, divorced teacher, aspiring novelist, and wine connoisseur, has agreed to take his old college friend, Jack, a struggling soap opera actor on a trip through California's wine country. Little do they know that their time together will be disastrous.

Jack is determined to get Miles, who manages to be both laughably insecure and absurdly pretentious, to lighten up and have some fun. But it soon becomes clear that Jack's real plan is to have as many emotionally devoid sexual encounters before he's married the following Saturday. As Miles and Jack travel through the scenic countryside, their friendship is tested and both are forced to see themselves for what they really are: two disillusioned, selfish, dishonest middle-aged men who never grew up.

While Miles sinks into an alcoholic abyss of depression, jack spends his time chasing as many skirts as he can. Yet things change when Jack invites Stephanie, a wine pourer at a local winery and Maya, an attractive waitress to join he and Miles for dinner. Their double-date ends with Miles and Maya making a real emotional connection, while Jack and Stephanie make a connection of a different kind. However, as Mile's feelings for Maya grow he is conflicted because of the fact that he and Jack have deceived the two women, having told them that Miles' latest novel is going to be published and not having told them of Jack's upcoming marriage. When the truth finally comes out the two friends find themselves in a tailspin. But in the end everything turns out okay. Sort of.


The cast 

The terrific cast includes Paul Giamatti as Miles, Thomas Haden Church as Jack, Virginia Madsen as Maya, and Sandra Oh as Stephanie. Paul Giamatti is wonderful as the neurotic and sarcastic Miles and Virginia Madsen is incredibly believable as the sensuous and intelligent Maya. Thomas Haden Church gives an impressive performance that shows his growth as an actor. And Sandra Oh gives a spirited performance in her portrayal of the saucy Stephanie.


The screenplay by Alexander Payne and Jim Taylor is hilarious and lends both depth and subtlety to the film's dysfunctional characters. Also Adding to the film's delightful atmosphere is the quirky music by Rolfe Kent.

Two men lost in life... 

Now Sideways may not appeal to all audiences. It is at times lewd and maybe even shocking, particularly when it comes to Jack's sexual escapades. Though I wasn't offended, more conservative viewers might be.

But this film isn't about sex.

It's about the  detours in life that unexpectedly change us forever.

As Miles regains his self-respect and Jack learns that his actions can and will have consequences, we, as viewers, get to laugh along with them and hopefully learn from their mistakes.

How to Drink Wine the Pretentious Way Drinking Too Much Maya Discusses Her Passion for Wine Double Date at the Winery Meaningful Chat

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July 15, 2010
Man it takes alot for a film to offend me and well this one did not, great review Count.
July 15, 2010
Again, thank you.
July 07, 2009
Loved the film and your review.....well-written, your review, that is, although the movie was a heck of a write! I especially like how you recap everything and the thoroughness of it. I've watched this film several times and see something new and different every time I screen it. On a higher level, the movie, I believe, makes us think about our own selves, how we conduct our lives, our level of maturity, and how we might have handled the dilemmas they encountered.....as you say, the detours that unexpectedly change us forever. I know I've learned a lot from this film and I hope others have as well. I'm now anxious to read the book.
April 17, 2009
nice review @Count_Orlok_22!!! i am such a big fan of the movie, that after watching it several times, i decided to read the book that the movie was based on, Sideways by Rex Pickett.. Outstanding book!!! it was really well written and highly entertaining, it was a lot of fun to read the book second and see the differences between the two... i'll share one little nugget.. when miles got really drunk the night before, he and jack would recap it as, "you were really sideways last night". funny, they don't share at any point in the movie the origin of its name, Sideways..
April 02, 2009
Great review, I am a Paul Giamatti fan, so I think I will have to check this movie out.
April 01, 2009
I am going to check this out- sounds like my type of movie-quirky, off the beaten path, and a little irreverent!
January 16, 2009
I'll find a way. I've got some pretty epic movie reviews planned for late winter and early spring, so I'll be keeping busy. :)
January 07, 2009
Nicely done. I did enjoy this film and thought it was surreal and enjoyable. How are you going to top your "watchmen" review now? ;)
July 21, 2010
been looking around for a review of yours I can feature and this came up again--I featured Hellboy instead.
July 21, 2010
July 21, 2010
LOL that's hilarious.  "I've been looking for a review to feature... this looks awesome, so I used your Hellboy one instead."
January 05, 2009
My daughter hated this film. Sometimes I listen to her, sometimes I don't. She tends to get a bit pretentious sometimes. But we both hated THE PIANO so I try and keep that in mind. She never did say what it was she didn't like about it though. Hmmm.
January 02, 2009
I actually had to watch it twice, to laugh. The first time I was busy wondering why in the world anyone would date those two. Miles whines with or without wine and Jack- well not sure I would offer water if he were on fire. As a side note the second time, with the shock worn off and half expecting to hate it.....I laughed my scrawny butt off- I would have left the wallet.
January 02, 2009
No doubt. Full-frontal nudity isn't necessarily a bad thing if it's part of the film's story. But having a 300-pound naked guy running after a car, while his member slaps against the car window, is another thing entirely. Nobody needed to see that!
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More Sideways (2005) reviews
review by . December 27, 2010
posted in Movie Hype
**** out of ****      Before I start things off, let me briefly discuss the art of illusion. You may go into "Sideways" thinking that it is a film about wine. However, the truth is that it is not a film about wine. Not strictly. It does INVOLVE wine, but never does it fixate solely upon it. Actually, "Sideways" never feels safe when it comes to focusing at one thing at a time, and that's why the end result is beautiful, moving, heartfelt, and hilarious. …
review by . July 30, 2009
I've eaten at the Hitching Post, AJ Spurs, and Los Olivos cafe, drank at Kalyra and Firestone wineries, seen the ostrich farm, had breakfast at the Solvang restaurant, slept at the Days Inn with the windmill and been to more wine festivals in the Santa Ynez Valley than I can keep straight. And, believe it or not, I did all of that before the movie "Sideways" was released.      THE PREMIER: So when I went to the film's premier in Santa Barbara …
Quick Tip by . August 10, 2010
Just an awesome movie and a great introduction to Pinot Noir and the Santa Barbara wine scene, in general!
Quick Tip by . July 12, 2010
posted in Movie Hype
The actors all did a great job in this movie, but it was hard for me to totally get into since I'm not into wine. However, the film was entertaining.
review by . July 12, 2009
When Sideways first came out in 2004, I was still in High School and I didn't think I would have an appreciation for this kind of movie even though I had seen many thought provoking and deep films already.  The idea to watch Sideways now stemmed from having our Wine tasting party (which actually, was never watched then, and was probably a good thing now that I think about it).  Because ya know, here we thought that Sideways was a film that focused around a bunch of wine snobs...I mean …
review by . January 03, 2010
Teacher and would-be writer Miles (Paul Giamatti) takes his actor pal Jack (Thomas Hayden Church) on a trip to the California wine country to celebrate Jack's impending marriage.  Miles is a wine lover and wants to educate Jack on the best wines, while Jack just wants to sew his last wild oats.      This is a dramedy about ordinary people dealing with frustration, failure, and loneliness.  Giamatti plays the sad-sack loser well, but his character is weak and unremarkable …
Quick Tip by . April 05, 2010
This movie became an instant "classic" and a must see for enophiles everywhere!
Quick Tip by . December 19, 2009
Sideways would be insufferable were it not for the great performances of the two leads, who make it an affable trifle of a movie.
review by . August 16, 2008
posted in Movie Hype
Sideways is a buddy movie about two flawed buddies who go off on a wine-tasting adventure in lieu of a bachelor party. The story is more melancholic than comic as the buddies each bump up against their disappointments and failures.   There are lots of reasons to watch this film. The acting is masterful, Sandra Oh is delectable and the scenery is-for most of us-a delight.What sets this movie up for a special place in my heart is one great wine joke.    There's a scene …
review by . May 28, 2006
"Sideways" has a fine premise for a movie: Two friends go traveling in Northern California to celebrate the freedom of bachelorhood before one of them gets married. Both have their own selfish interests and addictions: (One is addicted to alcohol [Paul Giamatti]; the other is addicted to sex [Thomas Hayden Church].) Their passions seem to be their only bond, for they increasingly separate from one another, each to pursue his own obsession. Their escapades reveal desperation for each and provide …
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About this movie


WithSideways, Paul Giamatti (American Splendor,Storytelling) has become an unlikely but engaging romantic lead. Struggling novelist and wine connoisseur Miles (Giamatti) takes his best friend Jack (Thomas Haden Church,Wings) on a wine-tasting tour of California vineyards for a kind of extended bachelor party. Almost immediately, Jack's insatiable need to sow some wild oats before his marriage leads them in into double-dates with a rambunctious wine pourer (Sandra Oh,Under the Tuscan Sun) and a recently divorce waitress (Virginia Madsen,The Hot Spot)--and Miles discovers a little hope that he hasn't let himself feel in a long time.Sidewaysis a modest but finely tuned film; with gentle compassion, it explores the failures, struggles, and lowered expectations of mid-life. Giamatti makes regret and self-loathing sympathetic, almost sweet. From the director ofElectionandAbout Schmidt.--Bret Fetzer

On the DVD
Stars Paul Giamatti and Thomas Haden Church have an absolute blast on their commentary track, gleefully ripping themselves, fawning over "La Madsen," and recalling "that bad fake wine we had to drink a lot of." Director Alexander Payne dismisses the seven deleted scenes (about 17 minutes total) as "meager offerings," and it's true that there are no gems. But even better than the scenes themselves might be Payne's text introductions, which offer insight into his editing process. Each scene is surrounded by brief bits from the ...
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Director: Alexander Payne
MPAA Rating: R
DVD Release Date: April 5, 2005
Runtime: 126 minutes
Studio: 20th Century Fox
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