The movie itself, in a meta-filmic way, is lying to you, the viewer.
— Paul Giamatti, commentary, Sideways
I hope you die.
— Stephanie (Sandra Oh), Sideways
Much like the characters they play in Sideways, Paul Giamatti and Thomas Haden Church regale on another with observations and jokes, witty and ironically self-congratulatory. “Sidebars of hilarity and poignancy,” announces Church at the start of the commentary track on Fox’s new DVD. “Excellent times, Paul, I think that’s where we’re headed.” At the same time, as Giamatti observes, “It is a picture about lying,” which means that any of the “badinage” on display here — both in the film and in the actors’ gloss on it — might be understood as fiction, spirited and self-knowing, reductive and repetitive.
Just so, Church and Giamatti recall not only the adventures they shared during production and their affection for “Herr Director” Alexander Payne, but also their understandings of their roles and the film (the DVD includes as well a selection of deleted scenes and a behind-the-scenes featurette). On one hand, they’re happy to joke about their own appearances (“My thickened middle age,” observes Church of his own first scene, while Giamatti notes of a close-up of himself, “Forehead like a sperm whale”), as well as their characters’ various crises and bad behaviors, not to mention that they are, as Church points out, “wholly unforgivable.”
Their adventure begins badly. Grumpy junior high school English teacher and unpublished novelist, Miles (Giamatti) means to take his old college roommate, sometime tv actor Jack (Church), on a holiday to celebrate Jack’s upcoming wedding. As they get into the car for a weeklong tour of the Santa Ynez Valley vineyards, Church watches and warns, “A lot of bad language in this picture. Get the kids out of the room.” Of course, cursing is the least of their problems. As much driving as they do in Sideways, both men are going nowhere. Miles still mutters over his abandonment by his ex-wife, his love of wine turned into alcoholism. For his part, Jack hardly seems ready to walk down an aisle, as sees the trip as a last chance for bedding every girl he meets.
Adapted from Rex Pickett’s novel by Payne and Jim Taylor, Sideways takes a skewed view of its road-buddy protagonists, as they judge and beat up on each other emotionally. Miles is uptight, Jack crass and narcissistic. And yet they find a certain solace in reproving one another, as it allows each to feel slightly less pathetic about his own stasis. As much fun as the actors have watching themselves — and one or both of them appears in nearly every scene here — the film is also bleak, indicated early on when on their first stop, an overnight visit to Miles’ mother. Watching Miles steal money from her “secret” hiding place, Church tells Giamatti that he’s already reaching “the pinnacle and/or nadir of your unlikability.” Indeed, he has nowhere to go from here. Seeing Jack stuck “in the emotional detritus between the son and the mother,” the actors laugh while appreciating the sheer awfulness of the moment.
Jack soon apprises Miles of his other ambition for the trip, to get his old friend laid as well. “You’ve been depressed for two years,” Jack says, “You need to get your joint worked on.” Sputtering, Miles is part horrified, part intrigued, and mostly miserable. He fixes on Jack’s carousing as a flagrant moral flaw, a confirmation that his personal rejection of the heathenish world is righteous.
The film neatly apportions the men’s self-evaluations according to their tastes and self-delusions. Jack knows nothing about wine, preferring to glug it as a means to an altered state; Miles is a self-instructed and arrogant connoisseur. He prefers and identifies with the sensitive, “temperamental” pinot noir, thinking cabernet too vulgar. As irritated as he is by Jack’s self-love (“I get chicks looking at me all the time, all eyes,” Jack asserts, “Men too”). He blithely lies up and down to Miles, claiming he’s read the latest draft of Miles’ novel when it’s clear he hasn’t.
Their conflict comes to a head over a woman, or more precisely, women. He gradually reveals his crush on wine-appreciating waitress Maya (Virginia Madsen). Jack sets up a double date, including pourer Stephanie (Sandra Oh). At Maya’s home late at night (as Jack and Stephanie make comically loud sex noises in the bedroom), Miles appears stunned by Maya’s beauty (or, as Church observes, she’s “bejugged and brainy.”) As Church enthuses about Giamatti’s much praised performance in the scene (“I smell an Emmy nomination,” he jokes, “I smell a Grammy”), Maya becomes the emblem of Miles’ desire and melancholy: “Look at her,” sighs Church, “She’s floating!” As the camera then closes on Miles and then Maya, she explains, “I like how wine continues to evolve. Like, if I opened a bottle of wine today, it would taste different than if I’d opened it on any other day. Because a bottle of wine is actually alive, and it’s constantly evolving and gaining complexity, until it peaks.”
Though it’s clear that Miles himself has “peaked,” he is also utterly seduced, and begins to imagine Maya might like him back. Always a resourceful, thoughtful performer (and nominated for a Supporting Oscar for this role), Madsen almost offsets Sideways‘ prosaic interest in the boys’ journey. While this journey ranges from depressed to eruptive, slapsticky to quirky, Madsen — low-voiced, watchful — holds your attention. And as much as Payne tends to make the same movie repeatedly, Maya is a surprise, granted more nuance than Jeannie Schmidt (Hope Davis) and less comedy than the redoubtable Tracy Flick (Reese Witherspoon).
Most reductively, Maya serves here to show Miles the way, to encourage him, in spite of himself, to be humble and open to feeling good for someone other than himself, to forgive Jack and also to move on from their competition. Though Miles first step is to see himself: “My life is half over,” he sighs to Jack, “And I have nothing to show for it, nothing. I’m a thumbprint on the window of a skyscraper. I’m a smudge of excrement on a tissue surging out to sea with a million tons of raw sewage.” Jack can’t stay down, admitting the creativity of his friend’s self-loathing (and, as Giamatti notes during this conversation, “It’s a toss-up who’s really the more sane person between these two guys”). Miles is deflated completely, as he admits it’s not even his own metaphor, but Bukoswki’s, as far as he can remember.
Amid the road-tripping and the boy bonding, it is Maya who resonates at last, especially once she’s exited the movie, hovering as a memory and a hope for Miles. In fact, she mostly exists offscreen, an ideal Miles describes before you see her, and an object of longing once he mucks up their budding relationship, essentially by his selfish passivity. All at the same time, Maya’s appearances are refreshing, grounded, and compassionate, alluding to the self that Miles might have been. If only.