A review requested by Matt U, with thanks for contributing to the Second Quinquennial Antagony & Ecstasy ACS Fundraiser.

Sideways, from 2004, is one of the more peculiar Zeitgeist hits of the 21st Century. It's a film about two rather dismal human beings acting generally horrible, and it puts all of its chips on metaphors about artisan-produced fine wine. Its happiest moments are all celebrations of the joy of eating fussily-prepared and undoubtedly costly food. It is in many ways suffocatingly snobbish, even as it generally positions itself as... well, not pro-snob, definitely, though "anti-snob" would be pushing it. Seriously, though, even the title (which was inherited from Rex Pickett's source novel, published earlier in the same year) is a reference to storing high-quality wine that's never given even the ghost of an explanation in the film itself. It's a movie that prefers for its audience to be reasonably well-versed in one of the most famously esoteric, costly, and elitist hobbies on the planet.

Despite this, it made a pretty huge impact, for what it is: $72 million just in the US against a $16 million budget, with enough people taking it into their hearts that there was a significant impact on the sale of Pinot noir (positively) and Merlot (negatively), thanks entirely to two of the most celebrated lines of dialogue in the film - and a noticeable upswing in the sales of wine in America generally. It snagged five Oscar nominations including Best Picture (winning for Best Adapted Screenplay), which was at the time regarded as a mildly surprising under-performance relative to how crazy in love with the film critics were. As they might well be: Sideways is all about the exquisite pleasures of being over-educated a subject and the ecstasy of having the vocabulary to express what makes it so particularly good; also about being a bookish, socially awkward white man of around 40. This does not, of course, explain why it struck a chord with audiences, and for that I think we have to go to that old chestnut, Great Characters, because the simple fact of the matter is that, buried underneath its exhaustive fascination with California wine country and wine itself, Sideways is a beautiful little chamber dramedy about four sharply-drawn characters played with a very lovely mixture of nuance and showmanship, by an unimpeachable cast made up of actors that absolutely nobody saw coming in 2004.

The film's a sort of a road movie, centered on two weirdly mismatched friends. Miles (Paul Giamatti, catapulting from "That Guy" character actordom into mainstream prominence, a year after American Splendor put him on the map with critics) is an attempted novelist reeling from a two-year-old divorce, and obsessed with wine to the point that it genuinely appear sto be the only thing he loves (that this allows him to semi-invisibly self-medicate with alcohol is obviously a happy accident). He's arranged a weeklong trip with his best friend Jack (Thomas Haden Church, then best-remembered, if at all, as the designated Extreme Moron on the 1990s sitcom Wings), a former TV actor now working as commercial voiceover artist, and a relentless, amoral horndog a week away from his wedding. The mere subject of their trip speaks volumes about what kind of men they are and how their relationship functions: Miles is taking Jack to the vineyards of Santa Barbara County to teach him how to appreciate wine, in a rather superior, "you poor idiot child" fashion. Jack, for his part, just seems to enjoy being out in the world, with his buddy, having fun. Not for nothing, but the one time we see Jack teaching Miles, when they're out golfing, he's enthusiastic and encouraging regardless of how bad Miles is.

The other half of the film's quartet are the two women the boys run into: Maya (Virginia Madsen, who'd been mucking about for years, and at 42 was at the worst possible age for a woman in the American film industry who wasn't an established star), a waitress at a restaurant in Buellton with a love of wine that can give Miles a run for his money, and Stephanie (Sandra Oh, a year before Grey's Anatomy premiered), a wine pourer at one of the local vineyards. It's a shame that, in a film which so finely parses the thorny friendship of two middle-aged men silently doubting their masculinity couldn't provide more for Maya and Stephanie to do than be "the women they get entangled with", particularly since writers Alexander Payne & Jim Taylor had already crafted outstanding female leads in two of their three prior collaborations, Citizen Ruth and Election (Payne, of course, directed both of those, as well as Sideways, as well as the duo's About Schmidt, another road movie about a sad-sack man figure some shit out along the way). But Sideways is already trying its luck at 124 minutes, and it's easier to imagine a broader psychological canvass bloating the film and breaking its delicate mood. Besides, even as largely functional characters, Maya and Stephanie still get plenty of shading and complexity; Maya, in particular, is front-and-center in the film's justifiably best-loved scene, in which she and Miles offer competing theories for how Wine Is Life. It's also rather impressive that a film which never joins the women's POV - never really departs from Miles, actually; it's basically a third-person limited narration done in movie form (the book was first-person from Miles's perspective) - positions us so thoroughly on their side, mostly by letting us watch in some small amount of horror as Miles and Jack behave abominably and give themselves leave to do so without moral self-reflection.

It's such a damn smart script; precise and elegant in its deployment of none-too-subtle metaphors, offering line after line of erudite but not showy dialogue that Giamatti and Madsen play in a variety of restrained tones (Giamatti even makes the broad-as-a-barn gibe "I am not drinking any fucking Merlot!" feel true to the character's frustration in that moment, and not like a laugh line). There are some odd digressions in the last third or so, including a lengthy passage that seems to exist primarily because Payne had previously gotten mileage out of a fat naked person and wanted to do it again, but the first half is airtight, capturing the cadences of adults of very different temperaments talking around all the things they want to say, spiked with just enough barbs for Giamatti to fling at Church that we remember that we are, after all, watching a comedy. By 2004, the great age of the American indie film as a commercially viable genre was starting to wind down, and in some ways, I think that Sideways is something of a last gasp of the "sensible grown-ups talking in quotidian settings" form - such films still exist, but they sure as hell don't clear $70 million any more (one of the few that had managed to do so in the 2010s is Payne's own The Descendants, written without Taylor and infinitely less forgiving, warm, and wise than this). Certainly, it's grown-ups are amazing characters, and while I don't think Sideways is Payne & Taylor's best film - Election will always win that title for me - Miles is easily their finest single character, a nasty, arrogant shit whose heart is bruised so badly that even when he thinks he's hiding it, it's right out for everyone to see and pity, a man that is quite impossible to like while being unbearably easy to empathise with. And it's Giamatti's best performance, too (it's everybody's best performance, let's not be coy here), making the character real in all his desperate, angry hurt, with asking or at times, permitting us to like him. But his unlikability isn't the sourness of Election, but deeply human.

The other lovely thing about Sideways is that it's really the only time in his career that Payne, a great director of actors and scripts, did much in the way of bringing some effective style to bear (of course, Nebraska is filled top-to-bottom with style; I simply deny that it's "effective"). Not everything works; there are a few montages scattered here and there, and not one of them is actually good, but all have a distinctly banal, soulless quality, golden-toned shots of people having strenuously relaxed fun. In some of these, Payne makes the astonishingly bad choice to include split-screens with the frames moving all around inside the main film frame, which only indicate that he's angry not to have been a filmmaker in the first half of the 1970s, the last time that this could have been done with any chance of working non-ironically. But get past that, and Sideways is a pretty sharp looking thing. It's handily the best-looking film ever shot by Phedon Papamichael, who uses a great deal of aggressive backlighting, complete with blown-out lens flares, to capture something of the essence of the California sun. In fact, this is a tremendous love letter to the Santa Ynez Valley and the laconic little towns there, all of them feeling strangely untouched by time, like life and aesthetics and culture stopped evolving in the '70s (at least in 2003 when the film was shot. The last time I was there myself was 1999, and it certainly had that "welcome to 1973" vibe; but then, more places did in the '90s than now), when the California wine industry burst into international consciousness. It makes for an excellent place to set a film: the landscape is gorgeous, naturally (is any crop so photogenic as vines?), but the human locations are generally quite attractive in their aged, slightly yellowed way as well.

But I was, anyway, going someplace quite different: the little grace notes of how Payne stages action, using depth to strongly accentuate the way that the characters inhabit the spaces where they're comfortable. Or the film's least-subtle moment, in which a very drunk Miles claws his way from the back of shot into the front, out-of-focus the whole way, a neat little way to emphasise inebriation that's as ham-fisted as Miles himself in that moment. It's quite nimbly done.

The film is charming and handsome, and so invested in figuring out its characters even when they're being crap, it's not at all hard to see why it was loved. Over-loved, maybe, by the portion of critics who identified too closely with Miles (judgmental, smug asshole that he is), but it's still a deeply satisfying movie. It's intimate storytelling, getting in good and close to interesting characters at an interesting time in their life; I would hesitate to call it "realistic", if only for the elaborate dialogue, but there's something comfortable and lived-in to so much of the movie. Time has treated it better than I thought it would, frankly, and while it's not at all one of the best films of the '00s, it's certainly one of the most inexhaustibly pleasant.