Sideways (2004)

Sideways (2004)
Sideways (2004) DVD / Blu-ray

By: Zack Mandell (A Toast) –

In 2011, writer/director Alexander Payne brought his film The Descendants to cinemas across the nation.  The film scored raves for its dark humor, its sensitive screenplay, and the sensational career-crowning performance from George Clooney.  Clooney’s films tend to attract a significant amount of attention.  It’s no wonder why: He’s the biggest movie star on the planet, save Brad Pitt.

This film garnered even more attention from the cinematic press however, not due exclusively to Clooney’s presence, but also because it marked Payne’s long awaited return to film.  “The Descendants was Payne’s first film in seven years, and it was a triumphant return, a return so triumphant that he scored his second Academy Award for Best Adapted Screenplay.  His first came for the last film he made before he disappeared.  That film was Sideways, and on a resume filled with gems, it is undeniably Payne’s signature work and his masterpiece.

If you don’t count the rewrite he did on “I Now Pronounce You Chuck and Larry.”

Of course, it’s easy to write a review for a film about an oenophile/belligerent boozer for a site that has a ratings system comprised of a designated amount of alcoholic beverages.  However, despite the film’s prevalent theme, Sideways receives a rating of one beer.  This film is about as perfect as any American film produced this side of the turn of the century.

Paul Giamatti, in a career defining performance, plays Miles, a failed novelist turned middle school English teacher who fosters an astute knowledge of wine.  Of course, that knowledge of wine masks his deepest character flaw: He’s an alcoholic posing as an expert of the finest wines.  Oh sure, he knows the proper etiquette at a wine tasting, and he knows what wines go best with what meals, but ultimately wine is a driving force in his post-divorce tailspin.  The spin picks up speed when he hits the road with his former college roommate Jack (Thomas Haden Church), a washed up TV actor looking to get his rocks off a week before his marriage.  Not just his rocks, but Miles’ is well.  When Jack finds out that Miles has a crush on an attractive waitress named Maya (Virginia Madsen), he forces Miles out of his comfort zone to decidedly mixed results.

A Toast

No one will ever confuse Payne with the great visual stylists of his era.  He’s simply not.  It’s not to say that his films are visually pedestrian, but he doesn’t have the idiosyncratic stylings of Wes Anderson or the grandiose ambitions of that other Anderson, Paul Thomas.  Where Payne excels is in his storytelling.  No contemporary director balances comedy and tragedy with such delicacy and precision, and Sideways is Payne at his finest.  Few directors can mine the dark humor out of divorce, depression, and alcohol fueled meltdowns, but Payne creates vivid characters, so vivid it’s hard to not recognize people you know on the screen.  The stories and situations feel very real, and in real life there is humor and tragedy attached, sometimes intertwined.  Sideways has one of the best screenplays committed to film over the last ten years.  Each character is fleshed out beautifully, and the dialogue is at turns hilarious and gutting.  And even though some would argue that wine functions merely as a plot device in the film, listen to Maya’s monologue to Miles about her love of wine, and you’ll realize what a perfectly constructed allegory it is.

Of course, as good as Payne’s characters are on the page, it’s helpful to enlist exceptional actors to fully realize them, and as he did with films like About Schmidt, Payne casts Sideways perfectly.  Paul Giamatti is frequently typecast as something of a sad sack, and he’s never been better than in this film.  He keeps Miles surprising.  We learn more and more about him as the film progresses, and Giamatti perfectly encapsulates Miles’ rarified air.  Even though Miles may think he is better than his troglodyte misbehaving road companion, he knows that in the end he is simply human, and therefore utterly flawed.

On the surface, Church serves as the film’s comedic relief, and boy the relief comes in waves.  He is responsible for many of the film’s funniest (and most sexually explicit) lines, but he slowly and beautifully peels away at Jack’s surface, showing us a lost and desperate man, caught in a life changing decision.  And rounding out the trio of Oscar worthy performances in the film is Virginia Madsen as the object of Miles’ affections.  Just like Miles, Maya is fresh off of a nasty divorce.  As a result, Maya sees the humanity in Miles’ tailspin, and the two become mirrors for the other.  She may have handled her divorce with a little more grace, but she still has the bitterness and despair she senses in Miles.  Madsen displays the complexities of Maya’s emotions and makes it look effortless.

Unfortunately, no actors won Golden Globes for this film.  This guy shows his golden globes in the film though.


Sideways is one of the great American films of recent memory.  At turns it is tragic (Miles’ drunk dial to his ex-wife), and at turns it is hilarious (even after several repeat viewings, the scene involving a lost wallet and a naked man leaves me in stitches).  Yet at all turns, Payne’s film is humanistic and real.


Drinking Game

Take a Drink: when Miles takes a drink (Although feel free to not dump an entire vat of wine all over yourself).

Take a Drink: when Jack says anything that would make your grandmother blush.

Take a Sip: whenever wine is discussed

About Zack Mandell

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