It’s a rare film that actually has a measurable impact on a completely unrelated industry. And for it to be such a sweet, low-key comedy like Sideways is, I think, almost unheard of. But after this film was a hit with audiences, sales of Pinot Noir skyrocketed while those of Merlot dipped slightly.
I sincerely doubt that the filmmakers went into this project aiming to reshape the wine industry. They were just trying to make a quiet, very human story about two friends on a road trip to celebrate an impending marriage and, in that effort, they very much succeeded.
Miles (Paul Giamatti) and Jack (Thomas Haden Church) are old friends. Miles is a depressed, frustrated writer working as a high-school teacher. He’s also a self-styled wine connoisseur with a fetish for Pinot Noir. Jack is an actor whose career is not exactly on the upswing, relegated to voicing the legalese that plays over prescription drug commercials. They’re heading up to the Santa Barbara wine country the week before Jack’s marriage, but the two men seem to have very different agenda. Miles is expecting a quiet week of wine tasting as the two old friends spend one last week before Jack’s life changes in a big way. Jack just wants to get laid before settling down.
Arriving in the wine country, they encounter Maya (Virginia Madsen), a newly divorced waitress that knows and clearly likes Miles, even if he is still in love with his ex-wife. They also meet her friend, Stephanie (Sandra Oh), the flirtatious pour girl at a wine tasting room who takes an instant shine to Jack. Imploring Miles to keep mum about his impending marriage, Jack pursues Stephanie by setting up a double date with her and Maya. Miles, who often has the social grace of a three-legged hippo, is left to fend for himself as Jack and Stephanie pair off. Despite his awkwardness, or perhaps because of it, the barriers between him and Maya start to crumble, if just for a little while.
Both men are interesting opposites. Gentle, kind and closed off, Miles acts as Jack’s ineffectual conscience and, for all his boorish womanizing, Jack seems to genuinely care for his friend, trying to force him out of the shell he’s built around himself. Unfortunately for him, Miles has a hard time keeping his mouth shut when he has a couple of glasses of Pinot Noir in him. As Maya, Virginia Madsen embodies the attractive, mature and intelligent woman that lonely middle-age bachelors dream of marrying. Sandra Oh, as the uninhibited Stephanie, is also a fantasy figure, but it’s a different kind of fantasy. She clearly knows what men want and wants that, too.
Like many small, character-driven films, the plot of Sideways doesn’t involve dramatic, life-changing events that forever alter the landscape of its characters’ lives. Instead, it just puts real, flawed characters together and lets them behave according to who they are. When movies have this kind of faith in the people inhabiting their stories, the result is usually magic, like with Sideways.