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#7 — Sideways (Alexander Payne, 2004)
Movies often trade in cataclysm and heartbreak, sending characters sprinting down rainswept streets chasing after that one urgent moment destined to change everything. That’s certainly stirring, but there’s also an inherent phoniness to it, a disconnect from the reality of most lives that are marked by incremental progress towards different levels of accomplishment and disappointment. Filmmakers are then measured by their capabilities as magicians, using the grandiose sleight of hand of their craft to obscure the falseness of each respective work with the conviction of the emotions, the elegance of the images, the uniqueness of the plotting and all the other elements that make the lack of veracity an utterly forgivable offense.

Then there are those films that take a different approach, that genuinely strive to get at something truthful, that indulge in deeply human moments that way that other films coat the screen with improbable wonders cooked up by special effects houses. Sideways is a film like that. It is very funny, and builds in juicy moments of humiliation and bravado for the actors. It is built on that handiest of structures, the road movie, which ensures that the next dramatic development is as easy to reach as the next town down the highway when you’ve got a dependable engine and full tank of gas. On this framework, Alexander Payne and his screenwriting partner Jim Taylor draw a quietly compelling portrait of the ways in which the approaching shadow of midlife, that point when you can no longer pretend that perpetually unfulfilled aspirations will somehow fortuitously fall into place, can exact its own brand of brutality.

The embodiment of this dilemma is Miles, played by Paul Giamatti. He’s an aspiring, unpublished novelist who teaches English to disinterested school children in order to make ends meet. Divorced and unhappy, his primary means of escaping from the tedium of his life involves cultivating an appreciative expertise of wine, a sideline that he puts to good use by taking his closest friend, a working actor named Jack who’s about to be married, on an extended weekend touring California wine country. Feeling that he’s about to give up his freedom, Jack pursues every hedonistic impulse he feels, urging Miles to do the same instead of following his usual track that leads to morose, hateful wallowing. “No going to the dark side!” Jack warns Miles before one particularly key dinner with some women they’ve met.

It’s another marker of the film’s quality that those women aren’t stock characters, the sort of generically sweet or enticing love interests that are usually deemed suitable for films about men clumsily finding their way in the world. Maya, the wine country waitress who Miles has long been charmed by, is played by Virginia Madsen with wells of resolve. She’s strained, but not broken, and a woman who proceeds gently into the world with a sense of hard-earned peace that explains as well as any other reason, and the reasons are plentiful, why Miles would be enamored with her. She carries with her the signs of contentment–the sort of contentment that only be achieved by someone with a maturity of spirit–that Miles covets the way he would a fine, rare bottle of wine. It’s just as elusive as that potable, as well. Then there’s Sandra Oh, portraying a winery worker who bestows generous pours upon the traveling pair before entering into a fling with Jack. Just as Maya is Mile’s missing ideal, so to is Oh’s Stephanie to Jack. She represents the freedom that he’s giving up, and the unassuming glee for life that Jack is futilely chasing by following his base instincts. Both Madsen and Oh take their relatively limited screen time and suggest full lives beyond the confines of the plot.

Payne’s film isn’t an anguished cry, nor is it a satire of midlife dismay, holding its characters up for chortles and ridicule. It is empathetic, knowing and kind, even as the characters make woefully misguided decisions. It extracts insightful, inspired comedy from the dull ache of underachievement, the sense that building a better life is a task that exists beyond one’s abilities, or at least least outside of the range of one’s battered, repeatedly thwarted ambition. Paul Giamatti and Thomas Haden Church, the two actors clearly charged with conveying this, are equally extraordinary as they follow different routes to the same sad-eyed conclusion. Church plays the actor who puts his pending betrothal in jeopardy with his actions, a man whose questionable motivations are so entangled that its difficult to discern when he’s playing a role. Is he convincing himself that he’s in love with this new conquest because of fears of stability, and the taming that comes with it? Or is the sobbing need for his wife to be that follows the real act? It may even be impossible for he himself to suss it out. It’s clear that his greatest skill is for covering his own tracks, crafting stories perfectly designed to make all his self-inflected wounds seem like the scars of bad fortune.

And yet he’s a consistently genial presence, hopelessly likable compared to Giamatti’s Miles. When Miles greets every glass of wine with a verbal dissertation on its charms and flaws, Church’s Jack is by his side, agreeable asserting that every swallow tastes pretty good to him. Miles is a tightly bound bundle of anguish, telling his own lies, engaging in his own masquerade. He recasts himself as better than he is–as a published author, as someone who hasn’t betrayed a confidence–and then braces himself for the inevitable fallout, tightening up in preparation for the emotional storms his deceits will unleash. It’s just another redundantly forlorn page in the book of his life, and Giamatti plays it all with appropriately draining precision, all the better to make the minor, ambiguous shift toward something more hopeful at the end all the more satisfying.

Ever since his feature debut, the scathing and hysterical abortion comedy Citizen Ruth, Alexander Payne has gotten more and more fearlessly real with each successive film, shuffling away from the safe buffer afforded by broad, pointed satire and challenged himself, and his audience, to grapple with he trickiest, stickiest human emotions, those that aren’t necessarily wrapped up tidily in time for a closing credits roll. And funny as Sideways is, it’s also got a sadness built into it, a veil of unnamed loss that’s settled over the characters. It never overwhelms the film, though, maybe because its most potent lessons involve the control everyone has over their own perception of their lot in life. After all, when you’ve got a bottle of ’61 Cheval Blanc, you’re the one that can determine the time and place of a special occasion.

(Posted simultaneously to “Jelly-Town!”)

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