We see the characters early on as the movie starts. Miles is supposed to be to his friend Jack’s house to take a week-long trip to wine country before Jack’s marriage to the beautiful Christine (Alysia Reiner). He’s late, of course, because he spent the night before out ‘wine tasting;’ Miles is a wine connoisseur, although he sometimes likes the effect a little more than the taste. He’s been reeling since his divorce from his ex-wife (Jessica Hecht) two years ago. He’s a middle school english teacher who wants to be a writer but keeps getting rejected. He drinks triple espressos, reads the New York Times, and pronounces croissant like French people do, ‘kwaa-sont.’ He also steals money from his mother sometimes and lives by antidepressants.
Jack is a simpler man. He wants this road trip to get away and have one last fling before his marriage to Christine. He also likes wine, but likes it in a simple way that has the effect to irk wine snobs. Wines that Miles states are sub-par or worse, Jack states with child-like confusion, “tastes good to me.” He’s a struggling actor; he used to play a major lead on “One Life to Live,” but now only does bank loan and skin ointment commercials. He wants to commit to Christine, but does’t know if he can. He also wants to live vicariously through Miles: it’s his goal, on his last week away before his wedding, to “get Miles laid” as a groom’s gift. The target in sight is Maya (Virginia Madsen), a lovely waitress at a restaurant in California wine country who has almost everything in common with Miles he could hope for—though Miles would be the last to know.
What works about “Sideways” is it doesn’t try to be what it’s not. This is not a film to watch for plot twists at the end, or discover neat, sewn-up conclusions that will make everything okay for everybody. Jack’s ‘plight,’ as he calls it, is one point of the movie; Miles being ‘stuck’ is the other. There’s comedy sprinkled throughout, some of the funnier instances the various times Jack chastises Miles for being too uptight, or Miles’ various meltdowns when his inner-core is threatened, but the film also offers more. Jack, despite his debauchery, is outgoing and confident—the very things Miles wants to be but can’t. But Jack also understands a good deal more. He doesn’t understand fine wine, movies, and literature, but he understands what drives Miles’ melancholy, even if his presentation is a bit lacking.
The performances, writing, and direction makes “Sideways” what it is, and the film indeed did win an Oscar for ‘Best Writing, Adapted Screenplay’ and a slew of other film festival wins. Giamatti and Haden Church are perfect together, sharing a chemistry not seen to this degree in some time. Giamatti, usually dynamic, his greatest skill here is showing Miles for all he is—despite the neurosis, despite his failures, and despite himself. With weaker writing, he’d be a caricature (in one scene he laments, after a rejection letter for his writing that, ‘I’m so insignificant I can’t even kill myself’), but here comes off as authentic and true. Who can’t understand a mid-life crisis where every wrench and even the kitchen sink are thrown at you in tandem?
Haden Church is equally great. And while he has hitherto had many a supporting role, here is able to come out of his skin and show us something this side of brilliant. Haden Church’s Jack is confident and full of himself—until he isn’t—and we see the rabid insecurity lurking under Jack’s veneer. He’s a box full of mismatched tools, lecturing Miles on letting go and trying something new while literally petrified to be married (and equally petrified not to be), and telling his friend never to give up on his dreams while being drawn, magnetically, towards leaving acting and doing just that.
But, under it all, Miles and Jack are just real. These are people you’d meet in a bar, at your work, in you neighborhood, etc., if you just got to know them. They experience clichéd emotions, but clichéd only because they are so real. Director Payne doesn’t moralize them—even when they behave badly—but merely lets us understand and sympathize.
Alongside them, Madsen, as Miles’ love interest, and Sandra Oh, as Jack’s ‘conquest’ Stephanie are perfect in their roles, and, smartly, are written as well and inclusive as their male counterparts, even if “Sideways” isn’t really about them. They offer varying degrees of complication; and just as the audience may question why Miles and Jack are friends, the same lens is cast on Maya and Stephanie. These are just people, people trying to find their way in life, and “Sideways” is shot like a painting you’re meant to look at and contemplate, but never fully understand. It’s more indie than Hollywood is used to seeing, and that’s a good thing.
“Sideways” is a wonderful film. It’s full of the kinds of things—such as friendship, camaraderie, and laughs—that draw us into a picture like this, but offers deeper treasure that slowly works its way in. It’s highlighted by a lighthearted soundtrack and cinematography by Phedon Papamichael that makes California and wine country warm, bright, intoxicating, and full of possibilities and desire (if you’re a wine lover, and you don’t want a glass after watching this film, there’s something wrong with you). Its sun-soaked bliss swirls around its lurking dramas, and even “Sideways’” slight predictability is forgivable among its greater treasures. Its ending is pensive and perfect; and the rest of it is indeed a trip worth taking.
