Sideways (2004, Alexander Payne) – Review

Alexander Payne directs this near perfect portrait of middle aged disappointment, regret, friendship and new beginnings.

Miles, ( Giamatti) a recently divorced, struggling author with a passion for wine heads off with his old college mate Jack on a wine tasting road-trip.  Miles is depressive, insecure, balding and struggling to come to terms with the fact that in his forties, he still hasn’t managed to make a success out of his career or love life.  He also drinks a lot and at times we’re left to contemplate whether his passion for wine is hiding a darker truth.  Jack, despite his stalled acting career, is an outgoing free spirit, with craggy good looks, a positive outlook and crass sense of humour.  They’re unlikely best friends, but their relationship is surprisingly touching.   On their jaunt into wine country Miles is hoping to have some quality bonding time with his old friend and send him off into married life by introducing him to the sophisticated art of wine tasting.  They’ll drink a selection of fine wines, eat gourmet locally raised food and play golf.  Jack, who is getting married the following week, is aiming to get laid, get Miles laid and drink Merlot.

Both the central performances are outstanding, but Giamatti is particularly impressive as the world-weary Miles.  It is one of those rare occasions where a well thought out and rounded character is scripted, cast and performed perfectly.   Everything from his slight hunch to his dress sense feels right.  On paper Miles doesn’t sound like the most affable of characters, but Giamatti brings a strangely endearing quality to his grumpiness and apparent lack of enjoyment of anything apart from wine.  He’s just an ordinary middle-aged bloke, whose life isn’t going the way he’d hoped.

“Half my life is over and I have nothing to show for it.  Nothing.  I’m a thumbprint on the window of a skyscraper. I’m a smudge of excrement on a tissue surging out to sea with a million tons of raw sewage.”

It is a film that will resonate with anyone who has ever found themselves troubled by the chasm between their lofty aspirations and modest mid-life achievements, but don’t worry if that sounds a little downbeat.  The most impressive aspect of Sideways is the balance between its dramatic ambitions as a portrait of middle aged depression, and the perfectly observed and diverse comedy.  There is dry, subtle humour derived from Miles’ snobbish wine-isms…

“One time we drank a 92 Opus 1 with smoked salmon and artichokes, but we didn’t care.”

… and a smattering of more vulgar humour as Jack attempts to squeeze as much getting laid and partying as possible into his final week as a single man.

Ultimately, Sideways is about one man and a middle-aged rut. At first glance the final scene may seem depressing, but it represents a positive change in Miles.  He has secretly cracked open his finest bottle of wine in a fast food restaurant, and rediscovered the ability to cut loose and enjoy his life.

One of the finest films of the 2000s.





  1. “One of the finest films of the 2000s.”


    A great, great flick. I think its about hope…

    The speeches that he and Virginia Madsen trade about wine are two of the greatest monologues ever, just complete awesomeness.

    Payne’s got a new flick coming out before years end you know.

  2. Pingback: Cinematic dialogue in Sideways | Cinema Shock

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