The hallmark of any good sports movie is that it makes you want to immediately go out and take up the contest for yourself. Sideways (2004) isn't all that different except that it makes you want to drink wine. Lots of it. Or even better, if you're within driving distance of one of our planet's rare, miraculously humid world-class wine regions, take an entire week to golf, picnic, and visit a different winery every night. If only life went as planned for director Alexander Payne's two hapless protagonists. Paul Giamatti stars as Miles, a fortyish, divorced middle-school English teacher who's hoping his first novel will be published. Wracked by stress while waiting to hear from his agent, it seems the perfect opportunity for a vacation particularly since Miles' best friend Jack (Thomas Haden Church) is due to be married within a week. Thus, with the top down on Miles' Saab, the two depart San Diego and head for the Santa Ynez Valley wine country, where they intend to lose themselves in vino and sunshine. There's just one hitch only a few days away from exchanging vows with his fiancée, Jack's determined to meet a girl. Actually, he just wants to get laid, and he quickly repurposes his vacation week into an old-fashioned frat-boy prowl. He's also determined to get Miles a hookup, but Miles' prolonged depression over his divorce and dead-end career prevents him from doing little more than lifting one wine glass after another until he runs into Maya (Virginia Madsen), an attractive waitress and aspiring vintner he's met once or twice before. And thanks to a careful bit of social engineering by Jack, Miles and Maya find themselves having dinner together, while Jack joins them with Stephanie (Sandra Oh), a sexy wine pourer he met earlier in the day. It's a graceful meal that leads to a romantic summer evening, but before long both men manage to undo their own good fortune, thanks to Jack's shameless duplicity and Miles' ceaseless nihilism, which he prefers to indulge while lost in a Pinot-colored fog.
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At the outset of Sideways we get a quick introduction to both Miles and Jack, and it's not hard to pigeonhole them as two-dimensional, categorical middle-aged men Miles the pudgy, balding, introverted intellectual, Jack the tall, blonde remnant of a strapping man about campus. In fact, the two are so distinct that it's hard to understand why they are old friends in the first place. It's a key bit of information that's withheld from us, and in fact one of the reasons why Sideways is such a thoroughly engaging picture character-oriented with an episodic, free-form plot, it's as much about discovering exactly who these men are as it is about their wine-country misadventures. With each unexpected turn we are given another piece of the puzzle: Miles is a detailed oenophile, a frustrated writer, a devastated divorcé, and a man who finds himself struggling over the value of honesty. Jack is just as capable of dishonesty, although he has an easy social charm that invites forgiveness, even when it's not solicited. But the fact that both men are so flawed or perhaps simply human is why they make amiable film companions, for we also are invited to see the complexity behind each façade. Miles' passion for wine masks his passion for life itself, but there is something admirable in the way he approaches a glass without any fear or equivocation it's almost as if he's a different person when he applies light and rigor and hierarchy to a new vintage. Similarly, the seemingly fearless Jack eventually reveals his own vulnerability to Miles, and its not hard to see that there's a small, occasionally frightened boy living within his over-the-hill teenager. Both are perfect fodder for director Payne and co-writer Jim Taylor in previous films Election and About Schmidt, Payne reveals an odd, touching sympathy for men who find themselves at one of life's crossroads (in addition to taking a somewhat sadistic glee a placing his characters in some very uncomfortable circumstances). Adapted from the novel by Rex Pickett, Payne and Taylor's script mixes absurd comedy with both drama and pathos (Miles' "drink-and-dial" scene is particularly cringe-worthy), while an entire late-night conversation between Miles and Maya seems on the surface to be about nothing but wine, but in fact is about themselves, their doubts, and their aspirations. And, of course, why Pinot is the hardest grape to grow. Fox's DVD release of Sideways features a very good anamorphic transfer (1.85:1) with Dolby Digital 5.1 audio. Extras include a commentary with stars Paul Giamatti and Thomas Haden Church, seven deleted scenes with notes from director Payne, and a "making-of" featurette (6 min.). Keep-case.