“Did you drink and dial?” Jack (Thomas Haden Church) asks Miles (Paul Giamatti) in Alexander Payne’s Sideways (2004) when Miles stumbles back to the table where the two friends are supposed to be entertaining their dates. As even Jack, who is hardly astute, already knows, Miles is doing what he always does: going over to “the dark side” of self-loathing when he ought to be enjoying the light banter of single women. After quaffing several bottles of expensive wine, Miles disappears into the recesses of the restaurant to call his recently remarried ex-wife in order to pick at the scabs of his broken heart. He informs her of his impulsive decision not to show up at Jack’s upcoming wedding – he won’t spoil her good time with his jealous despair. But like most disillusioned people, Miles can’t help spoiling everything by withdrawing into the citadel of self-pity. Opting out and making sure nothing happens, good or otherwise, is the last refuge of the hapless.

Sideways is a combination buddy-road movie, but while it features boorish frat behaviour and even a car crash of sorts, the film hardly belongs to a genre of macho adventurers taking to the open road. Here, the oddly paired friends tour the St. Ynez wine valley of California in pursuit of the perfect pinot noir. Payne and his co-screenwriter Jim Taylor’s adaptation of Rex Pickett’s novel explores the fussy manners of the oenophile. Miles is an accomplished wine taster, and therefore a patron of the exclusive and elusive. We see him snuffling drams of new wine, parsing their bouquets for “a soupçon of asparagus”. A good sample earns high praise – “it’s as tight as a nun’s asshole” – while inferior wine is dumped unceremoniously into a spittoon. Jack, who is being treated to this tour by Miles as a pre-wedding gift, is considerably less discriminating. He listens attentively to Miles’ pronouncements, but decides each glass “tastes pretty good to me”. Happily, though, Jack’s openness to the middling and meretricious is not a corrective for Miles’ own nun-like reserve, just as Miles’ exemplary selectivity does not refine Jack’s tasteless ways. Miles will learn to unclench a little as the story progresses, but as the title promises, there are no Hollywood revolutions of spirit or life-altering transformations. Life, for the most part, is a matter of moving sideways: we lose a little here, gain a little there, but seldom do we reach the heady heights of success or the ennobling depths of despair – at least not for very long before the apparent certainty of such moments is absorbed in life’s indifferent rhythm.

As Miles, an impecunious schoolteacher with a sophisticated palate, Giamatti manages the rare feat of appearing schlubby (1) and mandarin at the same time, and the combination is somehow appealing and sympathetic. If Miles is a not-quite-have-it with snobbish tastes, he doesn’t cut a ridiculous figure. Giamatti has a hangdog face, a thinking man’s physique, and a coward’s carriage, but he has an intensity that makes him somehow weirdly prepossessing despite those traits. It’s mostly in his eyes: they turn down at the corners and you think he’s a sad sack, but when he’s animated or angry, his eyes roll and flash. As Miles, Giamatti draws as much on the rage-full charlatan he played in the children’s movie Big Fat Liar as he does on the fractious authentic, Harvey Pekar, whom he portrayed in American Splendor (Robert Pulcini and Shari Springer Berman, 2003). But unlike Pekar, Miles can’t find a measure of political freedom in life’s limitations; he suffocates without the rarefied air of aesthetic perfection. At the same time, Miles is more generous than Pekar in allowing for human greed and pettiness – witness his friendship with the incorrigible Jack. Miles’ complaint isn’t so much with failed morals as with failed taste. Taste for Miles means the fulfilment of potential, and his chronic dissatisfaction stems from finding himself on the wrong side of the peak: the moment is unripe, or it has already soured.

Miles is waiting to see if his novel (which appears to weigh 20 pounds) will be published. As he describes it, it is the “partly autobiographical” story of a son taking care of his dying father, but then turns into a sort of “Robbe-Grillet mystery”. It’s not hard to see that Miles had begun with something real, something painful, but traded his instincts for something false and derivative, and it is not hard to anticipate he will have difficulty marketing the unwieldy tome. But wine, if precious, is not false: an excellent vintage epitomises the hard-won perfection he hasn’t found in work or love. For a man who has lost much and expects little, wine-tasting also offers Miles an empowering sense of expertise. It presents him with a world in which he has earned the right to move freely. Repeatedly rejected by publishing houses, Miles, as a connoisseur of wine, reserves the right to judge. Moreover, the film makes an implicit statement about America’s schizophrenic, debt-driven economy. More people raised with expectations of middle-class comfort are everyday disappointed, although not everyone is reduced, like Miles, to stealing money from their mothers to finance their exploits. Miles may exhibit all the classic signs of someone who feels the yawning maw of middle age preparing to engulf his dreams, but he is like many Americans of all ages who increasingly pursue luxury, or at least a whiff of it, at any cost. Living beyond one’s means seems the only life worth living, and if the St. Ynez Valley is “the poor man’s Napa/Sonoma valley”, as Pickett puts it in his novel, it will do in a pinch, just as the very cost of an overpriced cup of coffee is enough of a pick-me-up for those who can afford little else.


Thomas Haden Church’s Jack is a sincere, likeable cad, a leftover from Miles’ youth, the kind of guy you probably wouldn’t befriend now, but who keeps alive that less discriminating, and therefore less disappointed, person you once were. Jack’s a failed soap opera actor, still capable of wooing himself and women with cheap romantic dreams. On the verge of being married, he’s on the make, and tells the women they meet that they’re celebrating Miles’ novel’s imminent publication rather than his own imminent wedding. Miles must therefore live the lie of success, and he strains visibly against its discomfort. When Jack arranges for Miles and himself to go out with Stephanie (Sandrah Oh), a pour girl for a winery, and Maya (Virginia Madsen), a waitress Miles has known from a distance for some time, Miles can hardly be persuaded to seize the opportunity. Jack has no trouble seducing the equally lusty Stephanie, and for a time it seems Jack has stumbled upon the authentic life, prepared to take risks Miles dares not dream of. Miles, in lieu of making a pass at Maya, details for her his philosophy of wine-tasting. This is a risky move for Payne to have taken with an American audience, which is generally allergic to long, learned dialogues, but the actors hold up well under the weight of epicurean metaphors. Miles reveres the difficulty and rarity of achieving the perfect wine, which must be “coaxed until it reaches its full potential”. For Maya, however, wine is “a living thing” carrying not only its invisible history (the seasons, the oaken casks, the unrecorded lives of grape-pickers) as it “evolves”, but also “its inevitable decline”. Maya wants to embrace the whole messy spectrum of life; Miles prefers the perfect corpse.

But if Miles seems doomed in his perfectionist prison, there’s still something admirable in his outmoded purism. Payne seems to suggest dissatisfaction can be righteous, unappeasable. When Miles pours a bucket of wine over himself at a third-rate winery, he is ridiculous, yes, but his suffering is not. The moment is a good example of how effectively Pickett’s first-person novel translates into film, where it is perhaps improved. Payne might have opted for the voice-over as he did in About Schmidt; in that movie, Jack Nicholson’s voice-over keeps the audience apprised of each little change on Schmidt’s road trip of self-discovery. In Sideways, we have only Giamatti’s infinitely mobile facial expressions to guide us. When Miles stands there soaked and stained, we enjoy the pleasure of looking, of gaping, really, uncertain whether we are about to laugh in scorn or celebration or both. Payne also treats Miles’ dissatisfaction differently from Warren Schmidt’s. For one thing, Miles knows he’s dissatisfied, and why. His entire adult life has been a meticulous accounting of the ways life has failed to make good on his dreams of success and contentment. In Schmidt, Payne indulged in sentimentality: Schmidt greets the dawn a changed man after playing with his dead wife’s hideous figurines on the roof of his RV. Miles doesn’t have epiphanies, unless he’s gargling a first-rate wine. He’s too well acquainted with the ephemeral nature of revelation, which is perhaps why wine is so appealing to him: it’s about tasting, not swallowing (although Miles in his genteel alcoholism does plenty of guzzling) – it’s not supposed to outlive its momentary savour. And when Miles does indulge in some banal self-pity in a diner with a choice bottle of wine past its prime, self-pity seems the only extravagance he can afford, and we don’t begrudge him it.

The movie is filled with small, original, comic moments, and their cumulative effect is more responsible for maintaining the film’s leisurely pace than is Miles’ red jalopy. There is little that holds interest in the actual driving scenes: one vineyard, while pretty, looks like any other. The movie tries to convey the feeling of a carefree ride in the country with a close-up of Jack’s hand testing the wind resistance through the open car window; sunny music plays as the screen keeps splitting until it is filled with images of a hand riding the air current. Like a couple other unfortunate montages, such a shorthand technique of letting us know “a good time was had by all” seems forced and uninspired. More interesting are the hotel and restaurants Miles frequents, which look like overhauled relics of ’70s architecture. Their awkward “theminess” seems to supply an implicit, sad counterpoint to the urbanity of wine-country aestheticism: perfection-hunting inevitably devolves into tourism.

Sideways pits idealism and its inevitable disappointments against compromise and its probable satisfactions. It chooses the latter, but not unreservedly. The film ultimately conforms to the inflexible story arc of the romantic comedy: boy meets girl; snafus and hijinks ensue; boy and girl live, somehow or other, ever after in post-credits eternity. Much of the comedy, though, doesn’t arise from the romance that eventually develops between Miles and Maya, but from its degraded parody in the smarmy Jack’s romantic entanglements with any woman at hand. With Maya, a woman who has, unlike Miles, come through a recent, disillusioning divorce with a measure of grace and dignity, Miles must answer to her insistence, not upon good taste, but upon forthrightness and honesty. The sticking point in their relationship is Miles’ complicity in Jack’s rampant infidelity. The film shows a good measure of gender bipartisanship here: a “chick flick” might have demanded Miles forsake his caddish friend, and a manly-man film would have depicted Maya as meddling or unreasonable. As it is, Sideways chooses neither of these options, allowing Miles to choose both Jack and Maya as friends. Jack, who is forever needling Miles to have a good time, leaves a trail of destruction behind him from which he flees, literally, with balls in hand. After trying to keep Jack in line for most of the film, Miles finally gives into a fit of helpless laughter when Jack recounts a particularly unsavoury bit of mischief. Giamatti doesn’t need to scowl as much as he did in American Splendor to let us know what he finds distasteful. His big martyr’s eyes do all the talking, and in any case, the distasteful in Sideways rarely disappoints our finest sense: humour. Miles may never achieve immortal success as a writer – he may quit writing altogether – and the movie interestingly reserves a place for deserved discontentment, but ultimately he clings, as most of us do, to the mortal, unsung happiness we might find in love. Sideways has picked up seven Golden Globe nominations, and its popularity seems to arise from its allegiance to Freud’s dictum that all we should hope for in this life is reasonable unhappiness. We want to see our unredeemed failures writ large as much as (or perhaps more than) we want to live vicariously the Hollywood-style success that the movie tickets we keep buying at any cost make possible.


  1. “Schlubby” is pseudo-Yiddish for appearing sloppy, slobbish and slovenly, and carries a connotation of sadness.

About The Author

Natalie Reitano is a graduate student in English at the Graduate School and University Centre in New York City.

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