Sideways at Ten: Shut Up and Drink the Damn Merlot


Americans are awash in wine. We sniff it, eyeball it, drink it. We bathe in it.[1] It is a marker of cultural superiority and hipness. Things were not always so. For the Depression and Beat generations, wine was culturally denoted by the wino rather than the connoisseur. Even the heady Baby Boom generation, which drank a lot, preferred smart cocktails to Pinots and Chardonnay. So how on earth did wine enjoy such a turn around? Usually these things are complicated, but thankfully we can pin the entire wine revolution on one cultural moment: the theatrical release of Sideways in 2004. In the words of one authoritative and disinterested individual, Sideways “changed the international wine world indelibly.”[2]

Indelibly indeed, but let’s banish the hyperbole to the corner of the room for a moment. The wine revolution was well on its way before Sideways, with production and consumption steadily rising in the 1980s and 1990s. Moreover, wine was part of a wholesale shift in a much broader food and drink movement that emphasized artisanal production and local agriculture. Nonetheless, Sideways did play a part in shifting our culture. It made wine hip without sacrificing its integrity. It gave wine personality. It even attached a moral dimension to wine. Incredibly, the film did all of this and somehow avoided making wine douchey, which, let’s face it, is wine’s Achilles heel.

Sideways succeeded because it was authentic. The conversations about wine in the film were real. We learn, for instance, that California Chardonnay suffers from too much secondary malolactic fermentation and contact with oak. Pinot noir grapes eaten off the vine are sour, but show great potential for structure. But the film’s commitment to wine runs deeper than just getting the supporting dialogue right—it understands that authenticity is itself central to serious wine connoisseurship.

Pinot Noir Grapes
Pinot Noir

Pinning down the concept of authenticity is like that old adage about trying to nail jello to the wall. Authenticity means, first and foremost, that the wine you are drinking is the wine on the label—in other words, that the wine is not a counterfeit. But authentic wine is something more than this. It is wine made with integrity and care, and with respect for the traditions that give it a sense of place. Another word for this is the French term terroir. Sideways is indeed about California terroir, but the film’s use of wine and the idea of authenticity transcended wine’s production to include its consumption. This is no small matter. Consuming with integrity is a subject of immense importance for an audience of hipsters, professionals, students, artists and everyone else adrift in today’s world and suffering from chronic cases of neurasthenia.[4] To put this another way, wine is the perfect antidote to feelings of postmodern alienation. In a world where we consume cheap plastics and cloths produced under sweatshop conditions tens of thousands of miles away, where goods are becoming ever cheaper and disposable, and where profits are hoarded by faceless multinational corporations, authentic wine can connect us to the charm of the productive process. But only if we consume it right. Sideways is a lesson on how to do it right.

Not that this has anything to do with the film’s plot. Alexander Payne and Jim Taylor’s Sideways is a sweet story about Miles, a divorcee pressed into service as best man for his corrupt friend Jack, played with rakish charm by Thomas Haden Church. Miles wants to send off his friend in style, so takes him for a week of wine tasting and golfing in the Santa Ynez Valley. Jack just wants to get laid. A lot.[5]

Jack’s shallowness is apparent from the outset, but made all the more apparent by the depth Paul Giamatti gives to Miles as a man bested by the forces of family and marriage and career. His mother is a real piece of work. Half out of it, she is a nag who probably pushed Miles’s father to suicide. Miles teaches middle school while toiling away on a novel that no one will ever read. His ex-wife made him feel small and worthless then left him for a successful businessman. And Miles himself is no angel. In an unforgettable scene early in the movie, he pays a surprise visit to his mother for her birthday, which turns out to be a pretense for stealing some cash that she keeps hidden in the dresser drawer that holds her unmentionables.

sideways wine giamatti church

One must appreciate here the artistic risks taken by director Alexander Payne. The first few scenes of the movie establish two potentially unsympathetic characters—one lost in the depths of despair and the other lacking any depth at all. And they are failures to boot. Miles is a failed writer who spends the movie gearing up for the final rejection of his novel. Jack is an aging actor whose portfolio consists of commercials, voice-overs, and a stint as “Doctor Derek Somersby” in a soap opera. Marriage will be the end of even that meager career as his father-in-law has made clear that he will be brought into the family real estate business. Whatever dreams these two artists once had, they lost any tether to the real world a long time since. The week in wine country is a kind of final hurrah, where both men must come to grips with their irrelevance in the larger scheme of things.

It would have been easy for Payne to set the movie in wine country and leave it at that. After all, the movie really isn’t about wine—it is about Miles and Jack and the women they meet. But wine is more than just a prop, setting, or device. Wine unifies the movie, bringing together the characters and their interactions. Take Miles. He is judgmental and cranky, but somehow never quite devolves into a bore. And he genuinely wants to share this love of wine with his friend Jack. In fact, wine becomes the measure for the characters, who are all subtly judged by their understanding of and appreciation for it. We see this quite early in the film when Miles indignantly asks Jack if he is chewing gum during a wine tasting. Nor does Jack fare better as the film progresses. Jack’s assessment of every wine he encounters amounts to “seems pretty good to me,” or (even worse) repeating phrases that he has heard from someone else. One can fake wine literacy, as Jack tries to do, but it is transparent and hollow. Much like Jack.

The romantic interests of the film, Maya (for Miles) and Stephanie (for Jack) both reveal themselves through wine at poignant moments. Miles and Jack meet Stephanie (played by Sandra Oh) in a tasting room. She pours generously and gives them the company lines. The Cabernet Franc won a major award, she informs them. Miles dismisses it as flabby and overripe—typical for Cab Franc, Miles explains, a grape which will never deliver greatness. “I agree with you about the Cab Franc,” she said in a low voice, just to Miles. Later that evening in Stephanie’s kitchen (a wine-drenched dinner intervening), Miles surveys her wine collection and admits “I totally underestimated Stephanie.”

And he likely underestimated Maya as well. Played with rock-steady integrity by Virginia Madsen, Maya is recovering from divorce and working as a waitress. Like Miles, she has failed in her personal life. But her similarities with Miles end there. She is vibrant. She smiles. She is on a forward trajectory, in school studying horticulture. But her depth is communicated in a memorable scene where she critiques a wine that Miles has just paid a nice compliment. “Too much alcohol,” says Maia. “The winemakers overdid it.” Miles has just been shown up. And he smiles.


What follows may be one of the best romantic scenes in movie history. Maya clearly is interested in Miles, but not sure of the extent of her interest. Miles is cagey too. These are two wounded people, and the moment is awkward. They are alone on a porch in an unfamiliar house, they have both had too much to drink, and one room away their friends are copulating like wild animals. So they chit chat. Maya asks Miles why he loves Pinot Noir so much. A simple question, and the answer is lyrical. “It’s thin-skinned, he explains, “temperamental.” Unlike the vigorous Cabernet Sauvignon grape, which can thrive anywhere, “Pinot needs constant care and attention and in fact can only grow in specific little tucked-away corners of the world.” The truth about Pinot, says Miles, is that only “the most patient and nurturing growers” can coax from the grape its fullest expression. And when it happens, “its flavors are the most haunting and brilliant and subtle and thrilling and ancient on the planet.”

The audience knows that there is more self-description than not in Miles’s words, and we can’t help but be charmed by it. But nothing matches Maya’s soliloquy on wine’s deeper meaning:

I like to think about what was going on the year the grapes were growing, how the sun was shining that summer or if it rained… what the weather was like. I think about all those people who tended and picked the grapes, and if it’s an old wine, how many of them must be dead by now. I love how wine continues to evolve, how every time I open a bottle it’s going to taste different than if I had opened it on any other day. Because a bottle of wine is actually alive—it’s constantly evolving and gaining complexity. That is, until it peaks … and begins its steady, inevitable decline. And it tastes so fucking good.

Wow. Except that Miles manages to blow it. He breaks the romantic tension not with a kiss, but an awkward speech about Riesling, and then flees to the bathroom. This is a movie about living with failure, after all, and so we must allow Miles to be Miles.

But the aesthetic effect is remarkable. Miles’s genuine love for Pinot actually made the nerve-wracked Miles attractive to Maya. He understands the grape’s properties, its personality, and the care in its production. And what Maya and Miles share in this brilliant scene is not just a passion for wine, but a realization that their passion is important and real. And of course Miles blows the romantic moment. Otherwise the scene would have felt … false.[6]


And if there is any doubt that this is what defines authenticity, all one has to do is skip forward to the scene where Jack attempts to cheer up Miles by taking him to a fictitious winery brilliantly named “Frass Canyon,” which is a kind of inside joke for farmers. Frass Canyon is the antithesis of authenticity. Cheesy wine sculptures in the parking lot greet visitors. Tour buses vomit hoards of retirees in shorts and tennis shoes. Some guy plucks a guitar next to a fountain in a mammoth tasting room more dedicated to selling golf shirts and caps than to showcasing wine. Miles is not cheered up. He just wants a drink. The server is unwilling to oblige, admonishing Miles that “this is a winery, sir.” Paul Giamatti twists his face into a wry expression, cocks his head, and says “really?” It was not a question. The scene ends in brilliant comedy again, with Miles wrestling with the pourer for the bottle and, when he loses, drinking from the spit bucket.

Frass Canyon is the film’s metonym for Big Wine. The tasting rooms that Miles had taken Jack to were all small enterprises, family affairs. In an unsurprising move, director Alexander Payne had brought in real live winemakers in order to emphasize the connection between person and soil and finished product. By contrast, Frass Canyon (not a real winery) is impersonal and commercial. And the wine shows it. Miles gives his tasting notes: “Probably didn’t de-stem, hoping for some semblance of concentration, crushed it up with leaves and mice, wound up with this rancid tar and turpentine mouthwash bullshit.” The assessment equates the big winery with the assembly line—standardization and economies of scale become the opposite of the individual care and love that make wine beautiful.

Sonoma Rows
Sonoma rows

The juxtaposition is important. One of the charms of capitalism is its promise that the free market will reward the entrepreneur who makes things with genuine quality. It would follow that wine makers (or any artisanal producer) who make a quality product that is distinct from mass-produced baubles will be able to ply her trade and lead an honorable life. But we know this is just not true. Twenty wine firms account for roughly 90% of the U.S. domestic market. This is Big Wine, whether we are talking about corporate entities or private companies like Gallo. Over 7,000 small producers compete with each other for the remaining 10%. Often undercapitalized, lacking bargaining power with distributors, and facing the most confusing welter of regulations on the domestic sale of their product in the United States of any commodity, the deck is stacked against the mom-and-pop operations.[7]

Aware that the small market they compete for is interested in production, these wineries often market themselves just as much as their wine. Their websites have easy links to “our story,” and these stories are often personal in the extreme. But is this authentic? We hope so, but how do we know? Read the Gary Farrell wine story, for instance, and you cannot help but be impressed. Farrell started out driving tractors and trying to find work in Sonoma County before helping to lead the Pinot Noir revolution of the 1980s. (It is worth mentioning that Rex Pickett’s novel Sideways begins at a wine shop tasting where Gary Farrell Pinot Noirs are featured.) It’s a great story. The Gary Farrell winery is also owned by the private equity firm Vincraft Group, which bought it from Ascentia Wine Estates, which bought it from Constellation Brands (who did, in fact, buy the winery from Gary Farrell in 2004–after Rex Pickett wrote the novel). But to find such information, you have to poke around in the trade press.

So is Gary Farrell wine “authentic”? Is it corporate? Are these things mutually exclusive? I don’t think so. But for those who want authentic family-owned and operated wineries, the answer is probably yes. And testifying to the power of this desire for authenticity, you can still find these family operations tucked away on mountain roads, even in the hyper-capitalized Napa Valley. Why, for instance, has the world beaten a path to the Smith-Madrone winery on Spring Mountain in Napa—a winery that cannot be located on GPS, is sold in very few stores, and whose marketing campaign is the exact opposite of slick? As Stu Smith (one half of the Smith-Madrone pair, the other being his brother Charlie) put it, “Everybody says we’re authentic.” Then he added, “I’m not sure how you define authentic but we’re apparently it.”[8] Exactly.

Charlie Smith of the Smith-Madrone Winery
Charlie Smith, winemaker of the Smith-Madrone Winery

So authenticity cannot be manufactured. Except that it is. It can certainly be faked. And this is what brings us back to Sideways’s contribution, which is to remind us that there are standards, and that those standards denote integrity. One should recall the famous scene in which Jack admonishes his friend before dinner with Maya and Stephanie to take it easy, and informs him that, if the girls order Merlot, they are drinking Merlot. “No way,” Miles responds, “If anybody orders Merlot I am fucking leaving, I am NOT drinking Merlot.”

What’s wrong with Merlot? Actually, Miles is down on all the classic Bordeaux varietals, and this is one aspect of the screenplay that comes more directly out of Rex Pickett’s novel. Pickett’s Miles hardly resembles Alexander Payne’s and Jim Taylor’s Miles, but both do disparage the “blending grapes” of Bordeaux. Cabernet Franc is “overripe” and “flabby.” Cabernet Sauvignon is “prosaic.” He has no choice words for Merlot, but at that point it doesn’t matter—anything that could elicit this amount of passion speaks for itself.

But it’s less about what’s wrong with Merlot and more about what’s right about Pinot Noir. Pinot Noir is distinctive. It is a finicky grape, a notoriously difficult one to master, and one which can change fairly dramatically from growing year to growing year. No other grape more transparently communicates the soil of the vineyard. A prominent tasting note for Burgundy Pinots is “barnyard” for a good reason—it actually smells like shit and tastes like dirt. And some people will pay a thousand dollars a bottle for that privilege. Pinot is so reflective of its growing conditions and so capable of producing utterly distinctive wine, that many Pinots in California are designated not just by the vineyard, but by blocks within a single vineyard.

Pinot Noir in the Barrel
Pinot Noir, Sonoma County, Russian River Valley, Hallberg Vineyard, Block F

And that is Miles’s grape. But if Sideways had just used clever wine metaphors to represent the characters, this would not have been enough. It is Miles’s genuine love of wine that redeems him. It is Maya’s fine palate and her curiosity that give her depth. There is something profound in realizing that we all live in the interstices, that our passions are rarely if ever connected to the dull drudgery of work and the anxieties that accompany family.

The symbols in Sideways are not themselves without irony. Quite cleverly, Miles’s prize bottle is a 1961 Cheval Blanc. This venerable First Growth wine of Bordeaux is from the Right Bank, and is a Cabernet Franc-Merlot blend. So Miles’s prize wine, which we learn in the final scene of Sideways that Miles has been storing in the bottom of a closet in his San Diego apartment rather than in a temperature controlled cellar (and we must understand here that this is a wine which today retails for about $3000 a bottle, and would have been hard to get a hold of), Miles’s prize wine—which, by the way, he drinks from a Styrofoam cup while eating a hamburger and a side of onion rings at a grease joint—is, in fact, a Merlot.

This is significant. It would have been too easy for Miles to have been holding a Romanée-Conti—a prize Burgundian from the world’s most famous Pinot Noir region. To be an authentic wine connoisseur, Miles needed to understand exalted Merlots too. And yes, he would have to store them the way the most of us losers store them: in a closet, or in the basement, or under the stairs, but not in some temperature-controlled-stand-alone unit. Because most of us can’t afford that yuppy crap. You don’t need it anyway. Wine holds and ages just fine in the closet, provided it doesn’t get too hot and the temperature doesn’t swing wildly.

That touch of irony is a quiet exclamation point, drawing together elements of the idea of authenticity that pervade the film. All of Miles’s professional and personal failures have coalesced by the time he retreats to San Diego to fish the 1961 Cheval Blanc out of the closet. He has nothing left to lose. And in that profoundly human moment, he finds joy in the appreciation of something beautiful for its own sake.

Not all wine ages well. Most wine is made to be drunk and enjoyed immediately, and this has been true throughout history. The same is true of film, a medium dominated by corporate studios that produce a mountain of crappy pap that becomes dated quickly. But Sideways at ten shows structure. A second viewing can reveal its secondary characteristics, even if they were initially overwhelmed by the film’s comedic genius. So watch now, or any time over the next ten years. And pop the top on a Merlot when you do. Because fuck yes.

H. Robert Baker teaches history at Georgia State University. He writes primarily about the Constitution and slavery, having published two very good books on the subject. He is currently working on a book about Napa Valley in the 1970s and 80s. 


[1] No shit. (Accessed November 6, 2014).

[2] Rex Pickett, Biography. (Accessed October 10, 2014).

[3] We have all had at least one moment in our lives where someone, somewhere, tried to show us up about their knowledge of wine. Maybe it was at a dinner with friends that you haven’t seen since college and who are subtly judging you about how far you have (or have not) come. A fair number of us who love wine despise such doucheyness. Yet many of us have, at some point, also showed up some poor sap for not knowing enough about wine. Because it’s insulting when someone tells you that Yellowtail is good wine, that’s why.

[4] A disease marked by fatigue, depression, despair and feelings of helplessness and rootlessness in a world moving too fast around oneself. Neurasthenia was first diagnosed as an official disease in 1881. It was diagnosed almost solely in urban climates, and it afflicted people primarily of the professional classes, and mainly women. Treatments included bedrest, massive consumption of fresh milk, and, eventually, electroshock therapy. In the twentieth century, the disease was promptly cured by an act of psychological oblivion, by which I mean that psychologists and psychiatrists delivered the disease’s categorical imperatives into a state of oblivion after it was demonstrated to be a hodgepodge of ill-defined features that mainly correlate with the stresses of modern living. For this reason, many people today still struggle with undiagnosed neurasthenia for which no pharmaceutical company has yet devised a solution. Yet.

[5] Peter Travers made the same observation about Jack’s intentions in his introduction to Sideways: The Shooting Script (New York: Newmarket Press, 2004), vi.

[6] Part of the reason I have chosen “authenticity” to describe the filmmaker’s aesthetic choices regarding wine is that the movie itself painfully follows these characters where their character would take them. This is unlike the novel Sideways, which reads more like a version of Swingers with slightly older characters and a little more sophistication.

[7] James A. Thornton, American Wine Economics: An Exploration of the U.S. Wine Industry (Berkeley: University of California Press, 2013), 3, 149-179.

[8] Kip Davis, “Two Brothers Discovered Wine and Never Looked Back: How the Smith Brothers left Southern California to Create Smith-Madrone,” Napa Valley Register, September 5, 2013. From (Accessed November 6, 2014). For those who are interested, the “Madrone” in Smith-Madrone refers to a bunch of trees on the ranch they bought, which they left standing. So, yes, Smith-Madrone stands for two parts Smith and one part tree. More on Smith-Madrone in a later post.