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Sideways (Widescreen Edition) (2005)

A movie directed by Alexander Payne

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Should You Go Head Over Heels for Sideways?

  • Feb 2, 2005
  • by
Pros: acting, script, direction, humor

Cons: too long, main characters unlikable

The Bottom Line: It's a good year for Sideways.

By the time I got around to seeing Sideways, it had garnered so much praise that I was bound to be disappointed. Alexander Payne’s script (adapted from the novel by Rex Pickett) and direction are excellent, but the film is about twenty minutes too long, and the characters, while entertaining, aren’t likable enough. Payne should have made his two leading men either nicer or more attractive.

I’d love to be able to say that I found Miles’ (Paul Giamatti) relationship with Maya (Virginia Madsen) refreshing since he has such a non-Hollywood look, but, for me, it was just unrealistic. Besides, it’s not like a coupling between an ugly man and a beautiful woman is anything new. See any Jack Nicholson film. Everyone with whom I discuss Sideways says the same thing.

It’s a funny movie, but what does Virginia Madsen see in him?!?

When characters are played by handsome stars like Hugh Grant, we can forgive their moral transgressions since they are so pretty to look at, but Miles (Giamatti) could never be described as a sex symbol. The pudgy, balding, curmudgeonly high school English teacher hasn’t gotten over his recent divorce from Victoria (Jessica Hecht). To steal a phrase my grandfather used to describe Ben Stiller, Miles is entirely lacking charm. Failed novelists can be sexy, but they need to have a certain swagger and thick skin.

In an early scene, Payne shows Miles stealing a wad of cash from his mother’s sock drawer, which is a mistake on Payne’s part since it prejudices us against him for the rest of the movie. This detail also seems incongruous with the rest of Miles’ character, who is, essentially, a nice guy. He’s (possibly clinically) depressed and sulky, but he doesn’t seem like a criminal.

Miles’ best friend Jack (Thomas Haden Church) is a jerk who’s about to get married, so Miles takes him on journey up to California’s wine country, and their trip takes up the majority of the film. Jack doesn’t know anything about wine, so this trip is Miles’ idea of a good time even though it’s supposed be Jack’s bachelor party. Miles wants to drive around to vineyards, savoring various types of wine and discussing their properties. Jack just wants to drink and get laid. A former soap opera star, Jack is good-looking and charming in a sleazy way, but he’s a bit past his peak, to use a wine reference.

Wine is a good metaphor, but I felt that some of its use in this film was a bit heavy-handed. There’s one crucial scene where Miles is explaining to Maya why a certain kind of wine is his favorite, and it sounds like he’s describing himself. Not only does his monolog drag on, but his self-centeredness got on my nerves. Miles is so lacking in self-awareness that I wanted to reach into the screen and slap him at times. It’s obvious to everyone that Maya, for whatever reason, is romantically interested in Miles, but he doesn’t take the hint time and again. It’s painful to watch.

Rounding out the foursome is Stephanie (Sandra Oh), a spunky single mom who works at a vineyard. She falls for Jack, who, cad that he is, doesn’t tell her that he’s about to tie the knot.

Sideways has its slow moments of dialog, but the instances of physical humor are truly hilarious. It’s comical to watch Jack trying to learn the proper way to taste wine when he really wants to chug it, and Miles running and drinking from the bottle made me laugh out loud. In fact, for a film about something as high-brow as wine-tasting, Sideways has its share of crude humor, both in visuals and in the screenplay. It’s not for the faint of heart.

I agree with the common perception that Giamatti should have been nominated for an Oscar for his portrayal of Miles. He makes this complex character believable and plays both the sad sack and clown admirably. His face is amazingly expressive, and we can see his anguish and frustration in the way he carries himself. He’s also great at acting drunk, but I thought Payne has him sober up a bit too quickly. Jack and Miles drink a remarkable amount of wine throughout the movie.

There are moments when I thought Sideways might veer into psychologically deep territory like I Heart Huckabees does, but it generally stays in a romantic comedy/buddy movie zone. It’s definitely funny and unusual, but it’s not quite as classic as many reviewers seem to think it is. Maybe I should see it again in a few years to see how it ages.


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December 27, 2010
way to break it down..thanks!
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!
review by . January 02, 2009
posted in Movie Hype
How to Drink Wine the Pretentious Way
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.          …
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 …
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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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