In elementary school, my friends shared similar dreams of who they aspired to be: doctors, lawyers, astronauts, firefighters, veterinarians. When I was asked of my goals, I said sommelier. Kidding, but that would have explained my inexplicable love for Alexander Payne’s Sideways.
I’ve been sitting on this piece for months. Waiting to celebrate the 20th anniversary (eleven days from now, officially) of a film that I can watch again and again without it losing any of its luster. My capacity for impulse control should be a point of admiration.
Sideways is a film I’ll watch wherever, whenever—dropping everything at hand to do so. If I stumble onto it on [your choice of streaming service here], I’ll forget about what I originally intended to watch and press play. Or, if I’m channel-surfing (a pastime that’s dwindling more and more with each day) and see the title streaked across my screen, I’ll tune in, even if only for ten minutes.
Since the first time I watched Sideways, I’ve been obsessed with it. I can’t pinpoint why. Is it because the central character is a self-pitying, struggling novelist? Is it because it’s about wine (I don’t know anything about wine. In fact, I consider my oenophilic ignorance a glaring character flaw. Certainly, there is an inherent pretension in pontificating about wine. Gargling, inhaling the fruity undertones, imagining the calloused feet that stomped those grapes. But I have no problem with being pretentious. While most people look upon it with derision, I welcome it. Being pretentious is the preferable choice to being a philistine, barely able to discern white from red)? Is it because Paul Giamatti is the single most underrated leading man? I think it’s this last point.
Giamatti lacks the physical qualities that Hollywood has ascribed to the quintessential movie star. The abundant, effortlessly cool hair. The sharp jawline. The toned muscles and flat belly. Even in the characters he plays, he shirks the typical heroes, the ones who succeed and transcend the crippling harshness of reality. That leads me to the discovery of a particular penchant.
I am drawn to losers. The hapless. The down-on-their-luck. The neurotic and the self-deprecating. The under-achievers.
Who are the great losers in history? The Arizona Cardinals, in their 126 years (104 in the NFL), have never won a Super Bowl. Until recently, I thought they were a fictitious team, the home of Jerry Maguire’s Rod Tidwell. I shouldn’t talk. The Philadelphia legacy is not so immaculate, but we have our fair share of trophies across the board. Politics is abound with losers. In the 1936 election, for instance, FDR received a whopping 523 electoral votes (98.5%), while his opponent, Alfred M. Landon, secured a measly 8. Couldn’t even crack the double digits. The political losses are the most disheartening. Can you imagine the chagrin of knowing that such an astounding majority of the country doesn’t like you? There’s no reward for second place, either, when there’s only two of you running. But the most demoralizing loss has to be Thomas Dewey’s in 1948. The incumbent president Harry S. Truman was on his way out. Everyone said so, even Truman’s wife. The Chicago Daily Tribune sent the headline “Dewey Defeats Truman” to press. On the evening of November 2nd, the final votes amounted to 303 for Truman and 189 for Dewey. And Truman, as surprised as the rest of the country, flaunted the premature Tribune paper with a smile of delicious triumph. Poor Dewey. The only thing worse than losing is to have victory snatched from your fingers. Everyone’s favorite French emperor Napoleon I found himself tangled up in some now-famous imbroglios: the ill-advised 1812 campaign in Russia that saw him and his army stranded in the harsh Russian winter or the final nail in the coffin at Waterloo, where just about everyone turned on the once-glorious conqueror.
Losers are everywhere. You might be a loser. Even if you think you’re a winner, you’re probably a loser. Don’t worry, I’m a loser, too. Anyone that understands the precarious nature of life, the oscillations from the banal to the celestial, is a loser.
It’s much easier to be endearing as a loser than as a winner. No one likes the person for whom success falls in their lap. The chronically successful are usually submerged in their own ego. They can’t help it—were I to stumble into fortune instead of a brick wall, I wouldn’t stop yammering about me, myself, and I. By virtue of that, there is a perverse pleasure in witnessing them fail. Conversely, there is an indescribable glee in witnessing the losers succeed. It is the classic formula of storytelling. Conflicts and defeats lead to compelling narratives and complex characters. We need to be knocked down every once in a while. To retain our humility, our sympathy for the plighted members of society, our yearning.
In Sideways, Giamatti plays Miles, an unlucky in love, ailing novelist who daylights as an eight grade English teacher. He spends the remainder of his free time working on a tome that nobody wants to publish and taking trips up to Santa Ynez Valley where he can indulge the one truly pleasurable part of his existence. Miles’ old college roommate and friend out of convenience, Jack, is getting married, so they drive to wine country for his bachelor weekend. That’s it. That’s the film. How many times have I said that I’m much more inclined to watch a few compelling characters dig into their existential dread than to subject my eyeballs to the mindless, schizoid celluloid of a 40-minute car chase? Perhaps I’m alienating some readers and action movie fans. I do apologize, but to capitulate on my convictions would be disingenuous.
Problems arise, inevitably. Per the pre-wedding prerogative, Jack wants one final dalliance before he commits himself to monogamy. Jack has also told everyone that Miles’ magnum opus is getting published, which is a significant stretching of the truth. Then, there’s Maya: the waitress and aspiring horticulturist at a local restaurant who is fond of Miles—a fact of which Miles is painfully, or repressively, unaware. Her friend, Stephanie, becomes the object of infatuation for Jack who, in the span of two days, falls in love with her and very nearly decides to abandon his fiancée. In the wake of Jack’s bombastic promises, both women learn that he is on the precipice of tying the knot. Noses are broken, a cuckolded man flaps his phallus in the street, Saabs are crashed. The emotional mayhem that transpires over this botched bachelor weekend is enough to drive anyone into a depression.
Sideways shines when it focuses on the wine. That sounds obvious but it merits emphasis. Yes, the dialogue is brilliant (with Thomas Haden Church given the privilege of delivering the most memorable lines), the quartet of actors (Giamatti, Church, Virginia Madsen, and Sandra Oh) is delectable, but the true star of the film is wine.
For Miles, wine is a proxy for his personal relationships. Disappointed and divorced, committed to his romantic cynicism, he instead searches for, and finds, love in wine. Unequivocally, the best scene in Sideways is of Miles and Maya sitting on the porch and revealing the reasons for their attraction to wine. It’s a tender picture: under the golden glow of the porch light, legs hooked over the arm of a chair, a symphony of chirping grasshoppers in the background. As was made apparent early, Miles loathes merlot but can’t get enough of pinot noir. His explanation is exquisite and deeply personal: “It’s thin-skinned, temperamental, ripens early. It’s not a survivor like Cabernet, which can grow anywhere… Only somebody who really takes the time to understand Pinot's potential can then coax it into its fullest expression. Then, I mean, oh its flavors, they're just the most haunting and brilliant and thrilling and subtle and... ancient on the planet.”
His adoration is matched only by Maya’s musings on the process of cultivating wine: “I like to think about what was going on the year the grapes were growing; how the sun was shining; if it rained. I like to think about all the people who tended and picked the grapes. And if it's an old wine, how many of them must be dead by now. 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. That is, until it peaks, like your '61. And then it begins its steady, inevitable decline.”
It’s doubly tragic: Miles misses her cue inviting him to have sex. Retreating, instead, into the bathroom, he chastises himself: “You're such a fucking loser. You make me fucking sick.”
Sommeliers and dilettantes alike encourage you to let a bottle of wine breathe. I never considered that its requirement for oxygen makes it not so different from us. That it has to be cared for like a sentient being. A grape growing on a vine is rooted to the earth. It sources its sustenance from the soil, the rain, the sun, the air. Each variety has a different temperament and taste. Each variety requires a knowing, delicate hand. Is it so surprising, then, how closely linked we are to the natural world?
I’d like to make it out to Napa Valley one day or tour the vineyards of the French countryside. I’d like to swish a pinot or cabernet in my mouth and imagine its journey from the vines to the glass. I’d like to marvel at the nurturing it took to get there, the precision necessary to capture that fleeting moment when the grape is at its peak. Wine, certainly, is a romantic notion. There is a mystique to it—and whether it is a mystique or a veritable truth I have yet to determine—that by becoming fluent in the language of wine, you move one step closer towards understanding the elusive unknowns of the human condition.
You would think that a film about a moping, middle-aged, failed author might be discouraging. There seems to be little excitement in Miles’ life. The bachelor weekend—an event normally associated with debauchery—is, apart from Jack’s tempestuous affair, quite dull. Besotted from a string of wine tastings, the two men return to their shared hotel room, change into khaki slacks and patterned polos, then walk along the side of a highway to the Hitching Post where they drink more wine. Sometimes they play golf or take a dip in the pool. Remarkably, Miles’ circumstances continue to sour. One day, though, he receives that long-awaited call from Maya. She’s read his novel. She’s loved it. Although the publishers have rejected it, Miles is buoyed by the fact that Maya loves it. He drives back to Santa Ynez Valley. Bounding up the stairs to Maya’s apartment, he knocks on her door, and the film cuts to black. We don’t know what happens after—that would be too neat. What we’re left with is hope. After all the malaise and misfortune, we’re finally left with hope. Maybe we are losers, always dealt a bum deal. All it takes to change it is that one patient, gentle hand. The hand that can coax us into our fullest expression.