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In 2004, amid the latest Harry Potter, Shrek, and Spider-Man, themoviegoing public was shocked to discover they could actually see an American filmmade for grownups. In an era of widespread pandering to the child-in-us-all, criticslauded Alexander Payne’s comedy-drama Sideways for its adult themes andcharacters. As the critic David Ansen put it, “…Sideways stays resolutely life-size.And that, in this age of hype and hyperventilation, may be the most radical thing aboutit.” In addition to the financial achievement of grossing $110 million worldwide on aproduction budget of $16 million, Sideways has to be one of the best films evermade about wine; those who have seen it are probably doomed to hear the echo ofPaul Giamatti’s brief tirade against Merlot whenever they consider that varietal on a menu.

The film was Payne’s third in an escalating triptych of delving into middle-aged maleangst. In his dryly satirical semi-cult fave Election, the main character wascomically and blissfully unaware of his extreme American ordinariness, and his descentinto loserdom barely chipped away at an unrelenting optimism bordering on delusion.About Schmidt, a low-key star vehicle for Jack Nicholson, upped the self-awarenesslevel a notch, as the lifelong folly of a superannuated executive’s life slowlyseeped into his — and the audience’s — consciousness.

But in Sideways, Paul Giamatti, playing a guy who looks like Paul Giamatti, isalready in full-blown rueful mode when the film begins. The movie tracks a one-weekvacation in which his character, Miles, heads to the wine country of Santa Ynez Valley,in Santa Barbara County, with his pal Jack (Thomas Haden Church) on the eve ofJack’s wedding.

Miles is a junior high school English teacher, divorced three years and still pining for hisex. He’s also a talented but failed novelist, dependent on anti-depressants, and anabuser of wine. Jack is an actor who hit his peak as a regular on a soap opera but hasnow been relegated to commercials (“mostly nationals”). The two, of course, areopposites: Jack is a puerile loose cannon who effuses frequent bursts of cockeyedoptimism; Miles over-thinks everything and projects only doom. Jack is shallow, Miles anintellectual. Jack is confidently oversexed; Miles looks like he’d rather be anywhere elsewhen the lights are low. Jack is getting into a marriage he seems to not really want;Miles is out of one he still wants to be in. In short, Jack’s all id, Miles depressed superego. For Miles, the long-planned trip is a chance to school his buddy on the one thinghe’s still got a confident purchase on: wine. Jack, on the other hand, despite (or due to)his imminent nuptials, has the sole goal of getting laid.

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So that’s where the fun begins, as they used to say in sitcom promos. But despite someuproarious high jinks, the action really lies in the nuances of the characters’ interactionswith each other, as well as their different approaches to all things, big and small. Jack,for his part, is an inveterate bullshitter, the kind of guy whose magnetism will carry youalong to places you wouldn’t have normally dared — until you finally realize you’re inway over your head. Among several comically horrific plot points are Jack’s immediateinsinuation into the life of Stephanie (Sandra Oh), a woman he picks up on the trip.Within a day, he’s advanced the relationship to the stage of calling her, quite sincerely,”honey,” while she refers to him as Uncle Jack when he puts her daughter to bed. (Ohhas a fabulous scene in which she physically attacks him like a cartoon whirlwind afternews of his impending marriage leaks out.)

“All I know is that I’m an actor,” Jack says to Miles, explaining his thoughts aboutaborting his wedding in favor of this new relationship. “All I have is my instinct. You’reasking me to go against it… She smells different, she tastes different, she f***sdifferent.” This is both hilarious and horrifying: hilarious to hear a 40-something man saythose words as if he’s just hit upon an undiscovered truth; horrifying to hear such a thinrationalization for a form of semi-sociopathic behavior.

Miles, on the other hand, is all head. Payne paints his portrait in a few quick strokesearly on: reading on the toilet, ordering a spinach croissant with coffee, doing the Timescrossword while driving. But he’s also right on the border of being a prig. (He hits peakpretentiousness through use of the word “absolument.”) He’s also the kind of wine snoball but a true enophile would rather not hear from. “There’s the faintest soupcon ofasparagus and there’s just a flutter of like a nutty edam cheese,” he pronounces afterdipping his nose deep into a glass of red.

Yet, when meeting up with the soulful waitress Maya (Virginia Madsen), Miles’spersonality blooms. Suddenly he is downright cogent, even poetic. A fellow winecognoscente, she asks him about his deep affinity for Pinot.

“It’s thin-skinned, temperamental, ripens early,” he replies, speaking of the grape. “It’snot a survivor like Cabernet, which can just grow anywhere and even when it’sneglected. No, Pinot needs constant care and attention…and only the most patient andnurturing of growers can do it, really only somebody who really takes the time tounderstand Pinot’s potential can then coax it into its fullest expression. And then it’sflavors are just the most haunting and brilliant and thrilling and subtle.”

He has, of course, just described the best version of himself.

Sideways is one of those films that moves seamlessly from humor to existentialdesolation without stumbling over bathos. There’s an uproariously funny scene, forexample, of Jack giving chase to Miles, scrambling precariously down a steep hill whilestealing swigs from a wine bottle after he’s learned his ex-wife is getting remarried. Theflip side of that comedy: Paul Giamatti’s face as a portrait of poorly suppressed,crumbling despair when his ex tells him at Jack’s wedding that she’s pregnant.

It’s that poignancy brought to the character by Giamatti that pushes the film beyond thebounds of its comedic structure. Filled with self-loathing, Miles is always a hair triggeraway from what looks to be a total collapse. In one of the more memorably downbeatsequences I’ve seen on film, Miles and Jack pay a surprise trip to Miles’s mother on herbirthday. Only it becomes clear that he has made the detour in order to raid her secretstash of money so he can pay for the trip. As he does, he catches a glimpse of photosof himself, representing better days. He then sees his reflection in a mirror, where he isconfronted with just who he has become. That’s powerful enough, but Payne smoothlylayers on a related scene. The theft complete, Miles returns downstairs to find hismother in conversation with Jack, cooing over some inane commercials he’s appearedin. Coming right after Miles’s self-humiliation, it’s a nice connective moment betweentwo types of middle-aged defeat. Because if Miles reeks with the stench of unfulfilledpromise, Jack has a whiff of it himself.

Still, even given this kind of character depth, the film may have played out as merely anentertaining clash of opposites if not for Payne’s ability to thoroughly capture theemotional texture of certain moments and psychological states: the conviviality of analcohol-infused dinner; the tension of a first date eased by the sudden surprise ofconnection; the pain of missing the moment for a first kiss; and the loneliness of beingabandoned by a buddy. In this last sequence, Payne gives us a series of quick solitaryshots: Miles cutting his toenails, grading papers in a pool, calling voicemail devoid ofmessages, eating alone — small moments, still lifes, almost, adding up to a portrait ofbleakness.

In another standout scene, in which Miles “drunk dials” his ex-wife, shots ofhim thinking about making the call are intercut with the actual event, amplifying thetension between conception and execution of a truly bad idea. Here, the drunkenagitation of Miles’s state is captured with tight closeups shifting in and out of focus, as ifthe camera itself is half-drunk.

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Near the finish, the film cuts its comedy cord completely and goes to an even darkerplace. At the end of his tether, Miles surreptitiously steals sips from the pride of his winecollection while eating alone at a fast food restaurant. He was saving this particularbottle for a special occasion, and its premature opening represents the death of allhope. But the movie doesn’t end there. Like every vintage wine, Miles may yet have hismoment to peak. The last scene is open-ended, and with characters as rich as these,whatever happened next might have made a fine sequel.

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