The Hitching Post in Los Olivos is a pivotal location in the film. (photo by FiledIMAGE)

Alexander Payne’s close-to-the-bone 2004 Oscar-winning comedy Sideways earned substantial credit for successfully recasting the Hollywood buddy movie stereotype with a darker, more poignant, voice. As the film’s odd couple, former college roommates Miles (deliciously served up by Paul Giamatti) and Jack (portrayed with unapologetic shallowness by Thomas Haden Church) let us know that, while there is no doubt about the depth of their friendship and dedication to each other even as adults, as guys, they really share very little in common.

Miles is a middle-aged unrecovered divorcee and unsuccessful writer, whose only perceived tool to combat the chaos and disappointment of his life is his fandom of wine. When it comes to the grape, Miles knows the stats, and lords over that arena with strong opinions and a solid knowledge base. But, a good tool can also become a crutch. Jack, a charming actor hitting the skids, is about to marry into a wealthy family as an ersatz career exit strategy and is just looking to shamelessly exploit his “last days of freedom” on an out-of-town romp. When Miles suggests a wedding gift of a weeklong getaway to his familiar Santa Ynez Valley wine country hot spots on California’s central coast (some folks assume they go to Napa—not true!) to enjoy good drink and cuisine and get in a little golf, Jack eagerly agrees, albeit with his own agenda top of mind.

On the drive up, Jack audaciously digs into a bag in the back seat and pulls out a bottle that Miles implores him not to open. And here is where pinot noir enters the plot. It’s a bottle of rare 1992 Byron sparkling pinot, but it needs to be chilled, it’s a single-vintage sparkling pinot, they don’t even make it anymore… These protestations fall on deaf ears as Jack pops the cork and, emboldened by his friend’s spontaneous act, Miles actually allows himself to enjoy the wine, even in this unorthodox situation.

The film’s early tasting room scenes continue to draw the lines between the characters. In Lompoc’s Sanford Winery tasting room, Miles assails us with some hilarious, but from a strictly oenophile standpoint, right on the money, notes as he noses a Vin Gris. You have to give credit to this well-crafted dialog, but especially to its introduction of the ridiculous word soupçon (that is, “very small amount”) to the ever-growing lexicon of ridiculous wine words as he detects “…a soupçon of asparagus and a, oh, very tiny flutter of a nutty edam….” in the wine. This poetic waxing is usually countered by a “Yes, it tastes pretty good,” from Jack.

So, at the beginning, Miles’ intentions for the trip are going swimmingly. As for Jack’s more nefarious aims, the pair meet local waitress/grad student Maya (a pure sunbeam portrayed by Virginia Madsen), with whom Miles is somewhat familiar from previous trips, and hipster/tasting room pourer Stephanie (Sandra Oh in full-flirtation mode), and the foursome agree to meet for dinner at the landmark Wine Merchant Cafe in Los Olivos later on. In the interim, the pair enjoy some fine pinot noirs, notably the Bien Nacido and Highliner bottles from the Hitching Post II restaurant’s house vineyard; the legendary boite serves as their headquarters and is (as planned) walking distance from their hotel. Later, on his way into the date, Miles single-handedly cripples the global sales of merlot for about a decade by stating his ground rules: “…I am NOT drinking any f***g merlot!”

Maya’s subtle attraction to Miles is fairly obvious, but he lacks the confidence to pursue it effectively. Meanwhile as Stephanie and Jack gleefully enjoy their own animal attraction, Maya and Miles bond over wine. She impresses him with her selection of a rich Fiddlehead Cellars sauvignon blanc , but they also enjoy a series of excellent pinots from Whitcraft, Sea Smoke, and Kistler during the meal.

The group ends up at Stephanie’s bungalow to continue the party. Jack and Stephanie retire to a nearby bedroom; Miles continues to fumble any romantic opportunities by falling back into wine discussions. Still, the pair do manage some personal revelations that strengthen their connection. We learn that the gem of Miles’ bottle collection is a 1961 Chateau Cheval Blanc St. Emilion Grand Cru he’s been saving for a special occasion. Maya points out that simply opening a bottle like that IS its own special occasion, and we see Miles melt even more. By the time Maya asks him why he is so into pinots, we already know the answer.

“It’s a hard grape to grow, as you know,” he tells her. “It’s thin-skinned, temperamental. It’s not a survivor like cabernet that can grow anywhere and thrive even when neglected. Pinot needs constant care and attention, you know? And in fact it can only grow in these really specific, little, tucked away corners of the world. And, and only the most patient and nurturing of growers can do it, really. Only somebody who really takes the time… to understand pinot’s potential… can then coax it into its fullest expression.” So, there you have it. Miles is a human avatar of the grape itself, hobbled and intimidated by doubts around his own unrealized potential.

Of course, harsh reality rears its ugly head in this boozy paradise. The final nail is driven into the coffin on Miles’ hopes to get his novel published, and the truth about Jack’s impending, and by now, honestly desired, wedding is revealed. Jack is left literally battered (by Stephanie’s motorcycle helmet), and despite heartfelt apologies, Maya can’t bring herself to forgive Miles for supporting the deception.

The pair tuck tail and retreat home, managing to repair some of the damage and successfully save Jack’s wedding in signature ridiculous fashion involving an amorous BBQ waitress, a chase by a naked tow-truck driver, and a somewhat successfully faked automobile accident. At the wedding, Miles has his own successes; interacting with his ex-wife and her new husband in a confident, well-wishing manner and being additionally gutted by his ex’s revelation that she is pregnant without totally losing it. At a roadside burger joint, Miles, still in his dinner jacket from the event, bag-pours his cherished Cheval Blanc into a styrofoam cup to pair with what looks like a very nice cheeseburger. This bittersweet celebration is about his own ability to mature and get on with his life. As an aside not revealed in the film—but which caused knowing gasps to the wine cognoscenti—the Cheval Blanc itself is a Right Bank wine, primarily a blend of merlot (gasp!) and cab franc.

As final proof that Miles’ case is not hopeless, he receives a call from Maya. He left his novel with her to read when they were on good terms, and she admits she really liked it and would welcome a visit. The final scene sees Miles reach out to knock on Maya’s door, back in the Santa Ynez Valley. No doubt there is a superb bottle of pinot noir clutched tightly in his other hand.