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The ‘Sideways’ Revolution: How a Single Joke Upended the Wine World

Two decades after Alexander Payne’s boozy comedy became a surprise smash hit, its creators — and a host of top sommeliers — marvel at the movie’s lasting influence.

By Elycia Rubin

Elycia Rubin

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Alexander Payne had modest expectations for Sideways when his unassuming indie about an antic-filled buddy road trip through idyllic California wine country hit theaters in the fall of 2004. With an estimated budget of $16 million, the film wound up raking in more than $100 million worldwide and an Academy Award for best adapted screenplay — in addition to nominations for best picture, best director and best supporting actor (Thomas Haden Church) and actress (Virginia Madsen). 

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The line in question comes about halfway into the movie. Miles, the pinot noir fanatic played by a typically agitated Paul Giamatti, and his about-to-be-married friend Jack (Church) argue outside a Los Olivos restaurant in which their beguiling new acquaintances Maya (Madsen) and Stephanie (Sandra Oh) await. “If anyone orders merlot, I’m leaving,” Miles barks. “I am not drinking any fucking merlot!” 

Those 13 words would have an oracular effect, say sommeliers and industry experts, causing sales of merlot wines to plummet, to the benefit of Miles’ preferred varietal. This dynamic — measured in a 2009 Sonoma State University study that attributes it directly to the movie — was felt in winemaking regions across the globe, but especially in Santa Barbara County, where the film was shot. 

As suddenly as audiences abandoned Margo Channing for Eve Harrington in All About Eve , vintners and restaurateurs turned their attention from the bold merlot to the delicate pinot grape, the new star of the wine industry. Winemaker Doug Margerum, who owned The Wine Cask in Santa Barbara when Sideways was released, had a front-row seat. “We were having a hard time selling pinot then, but after the film came out, everyone wanted to drink it and sales skyrocketed,” he says. “We went from having one page of pinots on the wine list to three.”

Winemaker Kathy Joseph, of Santa Rita Hills’ Fiddlehead Cellars, credits the sudden popularity of the grape to the film’s lyricism about it. “I think people learned about pinot on a more spiritual level after the movie,” she says. “It gave them permission to start drinking more of it because it was described so elegantly, you wanted to be a part of that, and part of the romance of the wine becomes the romance of the region.” 

Miles expresses his love of pinot most fully in a soulful conversation with Maya, rhapsodizing about the varietal in anthropomorphic terms: “It’s a hard grape to grow. It’s thin-skinned, temperamental, ripens early. You know, it’s not a survivor like cabernet … No, pinot needs constant care and attention … and, I mean, its flavors are just the most haunting and brilliant and thrilling and subtle and ancient on the planet.” 

This ode to pinot owes a debt to the novel the film was based on. Miles is effectively the alter ego of Sideways author Rex Pickett, who still swoons over pinot. “I love its femininity and range of expression,” says Pickett. “Pinot inspires poetry and lyricism. It’s a bottomless ocean of mystery.”

No winemaking region felt the Sideways effect more than the Santa Ynez Valley, whose under-the-radar wines were propelled to star status. “When I would drive up while writing the book and even during the time of filming, it was undiscovered and rural and there was nothing high-end,” recalls Pickett. One of the winemaking pioneers of the region, fittingly, was actor Fess Parker, known for starring as Davy Crockett and Daniel Boone in the ’50s and ’60s. Parker established Fess Parker Winery, which — under a fictional name — served as the backdrop for the film’s climax, in which Miles guzzles from a spit bucket and then dumps the gallons of backwash on himself. Parker, who died in 2010, delighted in the business and press attention that followed the film’s release, vindicating his early bet on Santa Ynez. “He was extremely bullish on Santa Barbara County as a growing region and as a destination for hospitality,” says his daughter Ashley Parker Snider, “so those interviews allowed him to brag on the area a bit.”

The region has experienced significant growth over the past 20 years. “When Sideways was being filmed, we probably had around 100 wineries in the Santa Barbara wine country,” says Alison Laslett, CEO of Santa Barbara Vintners, a nonprofit organization that promotes the county as a leader in grape growing and winemaking. “Twenty years later, we now have well over 300 labels and around 75 different varieties.” 

New restaurants, several of them with Michelin recognition, flocked to the region, joining the Sideways -anointed standbys like The Hitching Post and Solvang Restaurant. Tasting rooms, meanwhile, exploded. 

In 2004, there were just a few perched in the quaint town of Los Olivos, and none in the Danish-inspired village of Solvang, long an epicenter of bakeries and tchotchke shops. “Tastings were free and there were barely any customers back then,” says Pickett. Today, you’ll find more than 30 of them, and fees range from $20 to $50. “For me, it’s the marriage of wine and the rural, magical beauty of Santa Ynez Valley,” adds Pickett, the region’s poet laureate. “Tasting rooms inspire and evoke conversation and bring people together.” 

Payne, for his part, believes that in capturing the charm of the region, he may have forever transformed it. “Every time I go, I feel more and more like a stranger in a strange land — all those new wineries, hotels and restaurants,” he says. “When I was there, everything was about joy, not commerce and tourism.”

Giamatti never shared his character’s obsession. “I had virtually no knowledge of wine before the movie and didn’t drink it much, and I still don’t know diddly about it and don’t drink it at all now,” he tells THR . “I’m not even sure what wine is what color. I feel badly because I disappoint fans and sommeliers all the time. I like Guinness and tequila. Not together, of course. Separately.” 

He, too, was recently in town and also wonders about the effects of the film’s success. “I was sad to see Pea Soup Andersen’s in Buellton was gone, but I was amazed by everything that has popped up in the interim,” he adds. “Changing the place so dramatically through making a film there is not something I ever imagined happening. I hope it’s been good for the folks who live there.”

While numerous vintners whose wines weren’t even featured in the film latched on to the coattails and rode the wave to a pinot bonanza, not everyone benefited from the liquid gold rush. Lane Tanner, another pioneering pinot winemaker who was married to Ostini prior to the film, had a vastly different experience after Sideways . “The movie screwed up my life so badly you wouldn’t believe it,” she says. “It was fabulous for the people who were shown in the movie — you couldn’t have had any better press — but it wasn’t great for all of us.” Demand for pinot grew faster than the supply, and the grapes became unaffordable for winemakers like Tanner. “Everyone decided they wanted to make pinot from Santa Barbara County after the movie, which made our grapes so expensive. Pinot is such a sensitive grape: only grows in certain areas, and needs that coastal influence — it’s very hard to make,” Tanner adds, echoing Miles’ soliloquy. “If you even look at pinot wrong while it’s fermenting, it can go bad. Three years later, everyone who was making cab was making pinot and they realized they couldn’t make pinot, so they were dumping it and basically giving it away.”

McCoy believes merlot is poised for a comeback — “be it a slow comeback,” he adds. “It’s easier to sell today than it was 10 years ago. I personally love a vibrant and elegant merlot. These often come from Coombsville, Carneros and the mountain appellations.”

Rebecca Phillips, owner of Buvette and Vintage Wine Bars in the San Fernando Valley, calls merlot “arguably one of the best grapes in the world” and believes the Sideways effect in fact stems from a misunderstanding.

“Within the context of the story, Miles never said merlot was a bad wine or a bad grape,” she notes. “Merlot has a lot of the same characteristics as cabernet sauvignon, so why throw the baby out with the bathwater? Sadly, filmgoers walked away from the film thinking they shouldn’t drink it, but true wine connoisseurs didn’t give up on their old-world merlots.” 

Margerum concurs: “The irony of the whole movie is that Miles is drinking Cheval Blanc at the end, which is primarily merlot,” says the winemaker of the final scene, in which Miles pairs a 1961 vintage of the exalted Bordeaux blend (in a Styrofoam cup) with a fast-food burger. “Merlot also happens to grow well in Santa Barbara County because it needs a colder climate, which is what we have.”

Beyond its role in the great pinot-merlot saga, Sideways helped demystify the often esoteric wine world and usher in a fresh wave of American oenophiles. Jared Hooper, sommelier and wine director for Santa Rosa’s Mayacama private golf club, believes the film changed the way Americans perceive wine. “I think it helped dispel the Frasier type aesthete snob model and bring in some true passion and respect,” he notes.

Madsen observed the evolution firsthand. “A lot of guys I knew who never drank wine started to experiment with it and discovered something new they could share in and enjoy,” she says. “And women were getting together and doing their own tastings. I love that part of it.” 

Payne is open to another film set in the world of wine, but with caveats. “Oh, man. Everything depends on the story,” he says. “I’d gladly return to oenophiliac cinema, but who are the people? What’s the story? Are there some good laughs in there?” 

Side -bar: The Santa Ynez Valley’s Wining and Dining Renaissance

Just as  Sideways  thrust Pinot Noir into the spotlight, the film also helped drive a surge in tourism to Santa Ynez Valley that shows few signs of abating. During the time of filming, there were just a handful of modest places to eat and stay, including two celebrated shooting locations,  Hitching Post  and  Solvang Restaurant , which still hold court as some of the most frequented establishments in town. But today, these down-home classics, which retain their original décor, now comingle with heaps of decorator-done, Michelin-level restaurants and hotels. 

The hotels that dot the valley today have also experienced a renaissance. “The Windmill Inn is now  Sideways Inn !” exclaims Virginia Madsen of the hip reimagination of the formerly drab motel where Miles and Jack cavorted in the film.  The Landsby , with its prime location in the heart of Solvang, oozes Scandinavian panache and is home to a lively bar scene and  Mad&Vin,  another dining hotspot.  The Genevieve  and  Hotel Ynez , both in Santa Ynez, offer swish décor and cozy outdoor spaces for gatherings.  Alisal Ranch , operating since 1946, is one of the most storied, sprawling getaways in the region and has unveiled remodeled guest rooms studded in modern Western décor.  Fess Parker Wine Country Inn , which also recently debuted renovated guest rooms, has been the longest standing luxury boutique hotel in the center of the historic town of Los Olivos. There’s even a high dose of swank with the nearby Auberge property —  The Inn at Mattei’s Tavern , which was once a stagecoach stop in the 1800’s, just unveiled a shiny new spa,  Lavender Barn  — the only lavish destination spa in town. 

A version of this story appeared in the Nov. 13 issue of The Hollywood Reporter magazine. Click here to subscribe .

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The Steady, Inevitable Decline: Sideways at 20

There are many to choose from, but the indelible moment in the both quaffable and transcendent " Sideways "— Alexander Payne 's now 20-year-old bummer masterpiece adaptation of Rex Pickett's novel about wine, middle age, and a distinctly American flavor of masculine failure and disappointment—has to be a pair of dueling monologues. We're in Santa Ynez Valley, country lodged in California's Central Coast that became infinitely more famous following the film becoming a critical, cultural hit. Miles is a struggling writer aglow in porchlight, on an evening cooled, like the grapes around him, by the air wafting off the Pacific. He's drinking Andrew Murray's Roasted Slope Syrah (Vintage unknown but Critic's Tasting Note for 2001: "A big disappointment") but talking about pinot noir, the grape he loves both for how it tastes, and how he perceives it, as a definitional varietal, a delicate , temperamental grape that explains a difficult , temperamental human being. If you're reading this, you can likely recite the speech by heart, but I'll quote it in full here as a testament to a truly great piece of writing:

"It's a hard grape to grow, as you know. Right? It's thin-skinned, temperamental, ripens early. It's not a survivor like Cabernet, which can just grow anywhere and uh, thrive even when it's neglected. No, Pinot needs constant care and attention. You know? And, in fact, it can only grow in these really specific, little, tucked-away corners of the world. And, and only the most patient and nurturing of growers can do it, really. 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."

This speech, and this film, not only had a great impact on you if you watched it in 2004, it changed the American relationship to wine, to the extent that it famously had a major impact on the American wine industry . It sent the production of pinot noir soaring in California, up 170% as of 2017, while at the same time depressing the market for Merlot, the grape Miles memorably detests. The irony is that this depiction of Miles, authored by the great aesthete/snob himself, is a joke made by the film that Miles is not in on. The central conflict of the film is internal, in fact. Miles is a Merlot who sees himself as a Pinot Noir. 

The bones for the film "Sideways" are in Rex Pickett's novel. Alexander Payne adapted it because he enjoyed wine (Like Maya, he was forever changed by a 1988 Sassicaia ), but also because he thought it would be easy due to how cleanly the story is laid out in Pickett's intensely personal manuscript. The film shadows the novel nearly plot-beat by beat, but with the necessary distance, gently adjusts our perspective of the protagonist. 

Alexander Payne was in the process of carving out a niche, making films often involved, if not centered around aging men in crisis from Kurtwood Smith to Matthew Broderick to Jack Nicholson. But he may have found his platonic muse in the neurotic schlemiel, Paul Giamatti . As Miles, Giamatti is playing older than he was in 2004, but was born deeply divorced, middle aged, paunchy, slope shouldered, eye ringed, downtrodden and draped in Men's Wearhouse, with a perpetually mussed hairline and sparsely occluded bald spot you can practically watch recede and thin throughout the film, attached to facial hair that looks more like a chinstrap tenuously connected to a goatee than a beard. The actor was the perfect symbol of fading masculinity for Payne to graft onto Miles, who in the novel is a former college baseball player. 

The film would be a career highlight for everyone involved, Payne included, largely thanks to a masterful casting job with the four leads. Giamatti had just broken out from what was shaping up to be a strong career in Hollywood's character actor, winging off the strength of a star turn as the comic book author Harvey Pekar, another nebbishy, soulful writer/loser in "American Splendor". The novel, the screenplay, and the film is first person. Giamatti, who is in every shot, has to carry the production on his back, and does. After "Sideways," Giamatti tips into full prosciutto mode, but here perhaps for the last time, he is recognizably, devastatingly human. His screen partner Thomas Haden Church would never again find this exact blend of vulnerable doofus, as the prosaic, lantern jawed, barrique chested Jack. He's a very familiar "type of guy", carved out of a block of American oak with a meat cleaver, not quite movie star hot but desperately clinging to post-handsome charisma, a balm and bomb of pussy driven energy, with a rich baritone voiceover offsetting Miles' reediness. Their easy chemistry makes both more likable in their perfect odd coupling of jock who lives in the moment and poet who can't. They are both narcissists, one overt, chasing youth, using women to reassure himself of his vitality, one burying his in self loathing and sabotage.

It was a breakout for Sandra Oh , Payne's then wife, who had served her time in a pre-prestige HBO "Arli$$" ghetto, but shines in her juiciest role here as a hard loving, sensualist tasting room bartender. And best of all is Virginia Madsen 's Maya, who had flirted with stardom several times throughout the '80s and '90s, but won a well-deserved supporting Oscar nomination for her work in this. In the novel, Maya is described as a hybrid of Greek Myth and American Gladiator. In the film, Maya is gorgeous, and deep, but has lived some life since her days of impossible beauty. She's still completely out of Miles' league, but has the right mix of believable relatability, a woman straining to see what she wants to see in Miles. And that word, "believability" is the governing mandate, the secret sauce of Payne's adaptation.

In a random year that saw Hollywood's continued death march to formulaic monotony in the form of apocalyptic CGI disaster films, aborted franchise starters, and the continued evolution of the comic book film, "Sideways" is disarming in how intimate the characters are, how low the stakes are. It's in the vein of the director's heroes Altman, Cassavetes, and Ashby: A chatty, drunken, two-man bachelor party up the coast with baby men being dragged kicking and screaming into middle age. Payne recasts what could've been a dark commercial romp a la Todd Phillips as a Jimmy Carter era character sketch treated with restraint and a lack of sentimentality, even in its manic and absurd moments of high comedy. 

It was lensed by Phedon Papamichael, capturing the Central California countryside's fluorescent signs and two-lane highway headlights that bloom on grainy film stock and lend the film its throwback, charming, handmade feel. Rolf Kent adds to this atmosphere with a score Payne wanted to swing like Chet Baker. He asked for jaunty, piano bar, smooth jazz pieces that arc over multiple scenes, bleeding from one to the next, which accomplishes setting an improvisational quality that runs through Kevin Tent's editing—pivoting from decanted long takes to rapid montages as fluidly as the tone oscillates between comedy and drama—and often feels novelistic in its unhurried discursiveness. It takes full advantage of Santa Ynez County and its glorious, wide shot golf course and grape tour vacation vistas imbued with a warmth you briefly want to live in and feels lived in.

We meet Miles several times at the outset of the film. He is badly hungover and struggling both with quotidian stressors of a life in shambles—getting ready to embark on his random freshman roommate at San Diego State's bachelor party—as well as the existential, stealing rent money and some spending cash for the trip from his mother's delicates drawer on her birthday. But the real introduction comes at the Sanford winery, the first stop on their trek, and our first opportunity to hear Miles cover his favorite subject. He instructs Jack, as didactically as possible, how to taste wine. And then, his insufferable tasting notes, "A little citrus. Maybe some strawberry. Passion fruit… and there's just, like, the faintest soupçon of like ... asparagus. And there's just a flutter of, like, a nutty Edam cheese." 

This is Miles, not the wilting, morose specter playing at meek shyness. He's an intense alcoholic steam roller, a Bukowski quoting neg head bloviating for 10-minute stretches on Vouvrays, a pretentious asshole who spouts profanity-barbed sarcasm at people not in on the joke. He's been crushed by life and his ex-wife, and he's in a two-year spiral of depression that he's been attempting to drown with Xanax, Lexapro, and Pinot Noir, dragging whoever is closest to him down in the process. It's the crucial distinction Payne makes that the novel didn't quite grasp. 

These foibles are heightened and exacerbated by the indecision looming over the film's action, which finds Miles in the liminal state any writer and most people waiting for word back on a big opportunity can relate to. The 750-page thorny and unfocused book he doesn't know how to end, that he's spent the tenure of his divorce torturing himself with, rejected everywhere by everyone, has at last reflected a faint glimmer of hope, some interest from a small indie publishing house called Conundrum. He spends his week on the central coast stewing in this ambiguity, compounded by his best friend's impending wedding and all the reminders of failure waiting for him in the form of his ex-wife and her new husband. 

The irony of the character is Miles is so tuned into his senses on a microscopic level when tasting wine. He is able to diagnose gradations of color at the edge of a pour, the layered scent when he buries his nose in a glass, the fungal note buried beneath the forward-facing fruit on the palate, but is lacking in self-awareness, both too hard on himself in his obsessive, myopic, narcissistic self-loathing, and too lenient, writing off his major, actually fixable failings on his own "delicate Pinot like sensitivities." 

Maya represents a relationship showing excellent potential for structure down the line. A miraculous opportunity for another shot at love and theoretical happiness, another beautiful woman who lives to eat good food, drink good wine, and share good conversation in good company. Yet she is a wheel that breaks Miles. The moment following his aforementioned grand speech about Pinot and Maya's Academy-recognized response—when Miles misses the perfect moment to move in for a kiss—was invented for the film and is nearly as remarkable as the speeches that set it up. It is the perfect encapsulation of Miles' headspace: Life throwing him a surreal fantasy, a made-for-screen heroic climax, and his inability to receive that love and joy. 

Something you begin to understand when you read "Sideways," watch the movie a few times and spend a month thinking about it is how wine can serve as a metaphor machine. Every person sees and tastes something different in a glass of wine, so it's a bottomless pour for writers who want to use it as a palette to interpret character. 

Merlot, Miles' ex-wife's favorite varietal, was a target of disdain in an unpublished draft of Pickett's novel, but was drawn out by Payne in his screenplay because, "Back then, it was the overproduced, over-marketed, over-consumed flabby wine." 

Bad Merlot, commercially mass-produced and over-extracted, high ABV with zero acid, deserves the film's mean-spirited ridicule. Historically, it was mostly utilized as a blending grape, contributing body, and clearing out for varietals with more character and nuance. But even good Merlot presents a challenge. A sturdy pour of a well-made, low-yield Saint-Émilion or structured Napa Merlot is strong and off-putting, and can leave your mouth tannin blasted like it was run through with sandpaper. It's an acquired taste that demands patience, space, time, and oxygen to find what can be plush fruit, creating a satisfying, balanced complexity worthy of pursuit. It wants to be paired with an aggressively aged ribeye to find its equal in heft and flavor, like Miles. Pinot has an incredibly high ceiling and a higher floor. It's accessible, and it's pretty comfort wine in a way Merlot can't be.

Payne understood this. In the novel, Miles is saving an 82' Latour, a special occasion bottle that he was supposed to open on his 10th wedding anniversary. It was a coincidence stolen from life. Pickett told me when he was younger, he too had an 82 Latour (he eventually sold during a rough stretch prior to writing the novel). But that Latour is a Bordeaux with 20% Merlot, Cab Franc, and Petit Verdot in its blend. When Latour denied usage of its brand in the film, Payne tried to get his hands on a Petrus from the Pomerol, which was 100% Merlot, but when that winery wouldn't play ball, he landed on a 61 Château Cheval Blanc, a mix of 58% Cab Franc (another varietal Miles shits on in his first meeting with Sandra Oh's Stephanie) to 42% Merlot. 61 was a famous vintage, but notably, the wine Payne selects is a full 20 years older than Pickett's Latour and has likely been held past its peak. None of this was a coincidence. 

Pickett, who was involved in every step of the writing and production of the film, says, "Alexander loves to pack the frame with production design. He loves to put in little subliminal Easter Eggs. And he loves to play on the contradictions of the characters. So he definitely knew what he was doing." It's the filmmaker and the film pointing out how little Miles understands about the world around him and himself that he presumes to be so certain of and how far he has to go.

Earlier this year, Giamatti reenacted the end of "Sideways" at an In N Out with his Cheval Blanc replaced by the Golden Globe he won for his performance in another 70s throwback called " The Holdovers ," which would sadly prove to be all he'd get for his reunion with his soulmate director. It was a savvy photo opp and wink for all the Giamatti heads, but he also reinforced the message at the core of this story about the nature of declivity in our lives: Not to hold that 40-year-old Cheval Blanc until it loses its fruit, not to let a kiss with a beautiful stranger pass, to appreciate the minor wins, the Merlots and Golden Globes life hands you when they present themselves because we are all dying slowly, our wine is turning to vinegar, and our best days may, in fact, be behind us. 

But today, or the day after yesterday, we can hope against hope that there's a romantically lit roadside bistro somewhere out there, with a few hours of good food and wine and warmth still waiting for us. There's a bottle intended for an anniversary that will never come we can unceremoniously uncork and pour into a styrofoam cup on our lap to relish with a shitty burger and a plate of onion rings. At any moment, we can drive two hours, march up a stairwell in Santa Ynez County, pound on a door, and live again. To grant Maya the well-deserved final word, "The day you open a 61' Cheval Blanc, that's the special occasion." 

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The Grape Escape

Sideways is the sweetest, funniest, most humane movie I’ve seen all year. I emphasize its humanity because most of what passes for comedy these days, whether it be low-concept or smarty-pants, is little more than gagfests peopled by joke-bots. In the movies and on television, it’s become hip to make comedies about nothing, à la Seinfeld and Curb Your Enthusiasm , or, in the case of I Love Huckabees , everything—which might as well be nothing. Frosty facetiousness is the signature style of the new “intellectual” American jape, and until now, I would have lumped Alexander Payne—who directed Sideways and adapted it from a Rex Pickett novel with his partner, Jim Taylor—into a mix that includes such prodigious smart alecks as Paul Thomas Anderson, the Coen brothers, and David O. Russell. In his previous feature films, Citizen Ruth, Election , and particularly About Schmidt , all of which were set in his native Nebraska, Payne was keen on displaying his own superiority to his characters. His movies were vehicles for vengeance against the heartland. (No yokel he.) But somewhere between his last film and his new one, Payne traded in his sarcasm for a soul. Maybe it has something to do with the fact that Sideways is set in the golden pastoral haze of California’s Central Coast wine country. Or maybe it was just all that wine.

Paul Giamatti’s Miles, a woebegone eighth-grade English teacher and would-be novelist, is the film’s unlikely Pinot aficionado who sets off from L.A. on a wine-tasting trip with Jack (Thomas Haden Church), an old college friend and washed-up actor, the week before Jack’s wedding. Miles is still sulking two years after his divorce from a woman he still pines for; Jack, who has large, rangy features and big hair and a surfer dude’s deep drawl, aims to cheer him up by getting him laid—a cure-all that he also reserves for himself. (He calls this trip his “last week of freedom.”) All the standard clichés are in place for a midlife-crisis, buddies-on-the-road movie, except that none of it plays out the way you’d expect. These guys may be an odd couple, but the mismatch makes psychological sense: Miles confers a connoisseurship on his friend, who doesn’t read much and thinks all wines taste pretty much the same; Jack stokes Miles’s id. If they had met as adults, they would probably not have connected, but college friendships are forged at a time when everyone is experimenting with who they are.

In each other’s company, the experiment resumes. Miles and Jack knock about as if they were still late-stage adolescents. They’re still figuring out who they want to be, which gives their strenuous efforts at happiness an added poignancy (and absurdity). We can see that Miles, who according to Jack has been “officially depressed for, like, two years,” is more than just a glum zhlub; he may not be able to get his book sold, but his love of language is as real as his love of the grape. When he talks about literature or his favorite wines, he isn’t showing off. He’s trying to live up to his own best image of himself, and he seems transported. In his own dim way, Jack understands this, which is why their friendship is more complicated than it appears. Jack is always telling the people they meet that Miles’s book is being published, and he isn’t being cruel—he’s trying to inspire Miles to be the guy he was before the two-year tailspin (and also get him some action).

“Paul Giamatti isn’t simply replaying Harvey Pekar from American Splendor —this is a whole other species of depresso.”

Miles has a wonderful monologue in which he rhapsodizes about the Pinot grape to a sympathetic waitress, Maya (an extraordinarily good Virginia Madsen). He calls it thin-skinned, temperamental, in need of constant care and attention. Of course, he is talking about himself. (Jack, by contrast, is a Cabernet that can grow anywhere and thrive even when neglected.) Miles is preternaturally sensitive to his own shortcomings. When Maya, who also knows her wine, leaves him an opening to make a pass, he lets the moment slide away, and his misery shines forth from his eyes like a death ray. Giamatti is letting us know that Miles’s eloquence about wine may just be a fancy way of tarting up his drinking habit, his sadness. But he isn’t simply replaying his Harvey Pekar from American Splendor —this is a whole other species of depresso: tender, enraged, rueful about what he has lost. At least Pekar was published.

One of the wonderful things about Sideways is that Payne gives its women equal standing (that’s why it’s not really a buddy movie). Maya is every bit as intricate as Miles—she has her own self-revealing monologue about how wine is “actually alive,” gaining complexity until its inevitable decline. But she’s blunter than he is. She tells him she loves wine because, when all is said and done, it “tastes so fucking good.” Hard knocks haven’t bruised her the way they have Miles; she’s still in the game, going for a degree in horticulture and taking things as they come. Miles may be one of those things, but she doesn’t press it—she respects his grief, and she’s also a little wary of it.

Maya’s friend Stephanie (Sandra Oh), a local wine pourer, is the film’s freest spirit, and an ideal playmate for Jack. Their carnal romps, at least until Stephanie finds out Jack is engaged, are great lewd slapstick. Miles chastises his friend, but it’s hard to argue with the guy’s life force, which is so outsize it’s comic. Jack has an actor’s penchant for playing everything center stage; when he’s recognized by a waitress for some crummy, long-ago soap-opera role, he acquires an imbecilic glow—he’s in clover. (Soon after, he’s in her bed.) Thomas Haden Church is known primarily for the inane sitcom Wings , so his performance here is a revelation: He gives depth to shallowness. Jack the satyr-narcissist is a figure of fun, but he harbors his own losses. That’s why he plumps up every time he’s noticed. He compensates for his show-business failure by converting the world into his very own playhouse.

Miles and Jack, in their own ways, are in awe of women—of their power to scramble a man’s good sense. Miles’s ex-wife, when we finally meet her, is no gorgon; she’s decent and intelligent and still cares about him, only not enough. With Miles, declarations of faith are supposed to be forever. He can’t abide the waywardness of affection, any more than he can abide someone who doesn’t love Pinot. In Sideways , wine is much more than wine. It’s a metaphor for the spirits that bring us to a reckoning with ourselves.

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Review: Aged to perfection, Alexander Payne’s ‘Sideways’ is worth more than a glance

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To be honest about Miles and Jack, something they never are about themselves, you’d have to admit they’re morally sketchy characters. Feckless and self-absorbed, they’re fraudulent even to their best friends, i.e. each other. Spending a week in their intimate company sounds like a chore, or worse.

It is the counterintuitive triumph of “Sideways,” the wonderful new film by Alexander Payne , to turn seven days with these scoundrels into a completely satisfying movie that quietly, gently blows you away. Exactly written, directed with a surgeon’s precision and transcendently acted, “Sideways” brings emotional reality to a consistently amusing character comedy, making it something to be cherished like the delicate Santa Ynez Valley wines that are the story’s vivid backdrop.

Doing achingly true-to-life films about out-of-control situations (“Election,” “About Schmidt”) has become second nature to Payne and his longtime writing partner, Jim Taylor. Here they once again mix unmixables, combining humor, pathos and genuine feelings in a way that’s warm, insightful and nonjudgmental.

But “Sideways,” based on a novel by Rex Pickett, also takes this team’s accomplishments to another level. After a raucous start with 1996’s “Citizen Ruth,” their films have gotten progressively more subtle, their comedy deeper, their themes more adult. With “Sideways,” their first grown-up relationship movie, they have increased the maturity content and explored the notion of the value and difficulty of intimacy without losing any of the playfulness that has been their trademark.

In this examination of individuals who, better late than never, arrive all unawares at turning points in their lives, the filmmakers have been helped beyond measure by their quartet of key cast members. While all four — Paul Giamatti and Thomas Haden Church as Miles and Jack, Virginia Madsen and Sandra Oh as Maya and Stephanie, the women who enter their lives — are actors with careers and reputations, none of them, and that includes “American Splendor” star Giamatti, has given the kind of rich, enduring performance they all do here.

“Sideways” opens with Miles, an eighth-grade English teacher and would-be novelist complete with worn corduroy jacket, doing what he does best: messing things up and avoiding the blame. Roused from bed because his battered red Saab convertible is blocking a driveway, he makes a frantic call to the person he’s supposed to meet, apologizes for being already late, and then proceeds to dawdle like the King of Siam, royally taking his time and baldly lying that traffic held him up.

The person he’s meeting is Jack, Miles’ best friend and former college roommate. An actor reduced to Spray ‘n Wash voice-overs after a career that peaked playing a dashing doctor on an afternoon soap, Jack is getting married in exactly one week. Miles, the future best man, is taking his pal on a trip to the area just north of Santa Barbara, intent on helping Jack spend his “last week of freedom” indulging in fine dining, great scenery, unforgettable golf. And wine. Lots and lots of wine.

For wine is Miles’ consuming passion, the great enthusiasm of his life. Listening to him talk wine is an education in itself, and he caresses grapes on the vine as if they were his true best friends. The kind of connoisseur who means it when he says “if anyone orders merlot, we’re leaving,” Miles can make judgments like “quaffable but far from transcendent” sound perfectly reasonable. And here he is paired up with Jack, who has to be told not to chew gum while tasting and thinks nothing of opening a warm bottle of expensive champagne if he’s in a celebratory mood.

As we discover on the drive, there is this opposites-attract, Mr. Inside/Mr. Outside quality to the Miles-Jack relationship that makes their friendship plausible. While pessimistic Miles holds back, reluctant, for instance, to even discuss his years-in-the-making 750-page manuscript that’s slowly making the rounds in Manhattan, Jack tells everyone who’ll listen that it’s about to be published.

Miles, fighting divorce-induced depression and used to approaching things sideways rather than head on, is frustrated by but also envies Jack’s wholehearted embracing of life. The actor, meanwhile, knows he could use some of his friend’s gravitas. These are men who often know what is best for each other, never for themselves.

Inevitably, romantic complications insinuate themselves into this jaunt. Jack, always the creature of impulse, is immediately attracted to the vivacious Stephanie, a tart-tongued pourer at a tasting room. And Miles, with insistent prodding from Jack, realizes that Maya, a waitress he’s thought of as only a pal, is more attractive and more potentially interested in him than he’d allowed himself to notice. With the players set and enough wine flowing to make everyone as close to merry as they ever get, the games are free to begin in earnest.

It’s in its willingness to be insightful as well as evenhanded with its characters, to completely understand but never whitewash behavior, that “Sideways” is especially potent. The film reveals vulnerabilities, insecurities, not-so-occasional miscalculations, but it also makes us care about its people while recognizing that they, like the rest of us, are nothing if not flawed.

Grounded in this kind of reality, “Sideways” works beautifully on any number of levels, from the at-times bawdily comedic to the genuinely heartbreaking. Cinematographer Phedon Papamichael has given it a bright look, Rolfe Kent has provided an inviting jazz score, and even the smallest characters are expertly cast thanks to casting director John Jackson. But again and again it is the four leads whose performances make all the difference.

As the self-doubting Miles, a man for whom every night is the dark night of the soul, Giamatti makes the best use of his querulous persona, investing an unerring comic touch in a character who is genuinely anguished. When Miles says, in one of the film’s best moments, that “only when someone has taken the time to truly understand its potential can Pinot be coaxed into its fullest expression,” he’s obviously talking about himself.

Haden Church, best known for his TV work (“Ned and Stacey,” “Wings”), brings unexpected empathy and a gift for deadpan double takes and open-mouthed befuddlement to Jack, a bluff Lothario increasingly gone to seed. He is beautifully matched by Oh (Payne’s wife), who brings a captivating mixture of sensuality and directness to the woman who’s the focus of Jack’s attention.

Though the women in “Sideways” are not given as much screen time as the men, they’re written with equal skill and are essential to the film’s success. This is especially true of Maya, a character who carries the burden of being its most humane voice. Madsen’s ability to bring delicacy, sincerity and soulful strength to a caring, grounded individual gives the film an emotional integrity it would be immeasurably less effective without.

Madsen’s performance, as it turned out, was of special interest for me. When the actress came to Hollywood some 20 years ago, I was assigned to interview her for a magazine profile, and I’ve never forgotten the purity of her youthful ardor to do significant work. Though her resume is extensive, she never seemed to quite get the opportunity to fulfill those early dreams. And now she has. In a town noticeably lacking in happy endings, it must be gratifying for her and for all the actors who come to Los Angeles hoping to find material as exceptional as this and a director who believes they have the ability to handle it. A film like “Sideways” is the fulfillment of many hopes and desires, an audience’s not least of all.

'Sideways'

MPAA rating: R for language, some strong sexual content and nudity Times guidelines: Graphic sexual situations, full frontal male nudity Paul Giamatti…Miles Thomas Haden Church…Jack Virginia Madsen…Maya Sandra Oh…Stephanie A Michael London production, released by Fox Searchlight Pictures. Director Alexander Payne. Producer Michael London. Screenplay by Alexander Payne and Jim Taylor, based on the novel by Rex Pickett. Cinematographer Phedon Papamichael. Editor Kevin Tent. Costumes Wendy Chuck. Music Rolfe Kent. Production design Jane Ann Stewart. Art director Timothy Kirkpatrick. Set decorators Barbara Haberecht, Lisa Fischer. Running time: 2 hours, 4 minutes. Exclusively at Pacific’s The Grove Stadium 14, 189 The Grove Drive (at Third Street), (323) 692-0829; and Laemmle’s Monica 4-Plex, 1332 2nd St., Santa Monica, (310) 394-9741.

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Sideways Reviews

Giamatti, although overlooked by the Academy, serves as the emotional anchor of the film, holding its narrative together with his compelling performance.

Full Review | Original Score: 5/5 | Oct 22, 2024

Alexander Payne’s road movie about best friends taking a bachelor party on the road through California vineyard country is a modern buddy film with a seventies sensibility.

Full Review | Jan 6, 2024

Payne is a compassionate observer here, letting the dialogue scenes breathe, unafraid to throw in some slapstick.

Full Review | Original Score: B | Sep 19, 2022

It is a powerfully written story captured onscreen by Alexander Payne with a wondrous humanity and sensitivity.

Full Review | Original Score: 4.0/4.0 | Sep 23, 2020

This is a film about human beings who can be flawed and prickly but if you go a little deeper, you will see beauty. This is a wonderfully written script, with a great performance by Paul Giamatti.

Full Review | May 18, 2020

Funny, touching, and features perhaps the best ensemble work of any film in recent memory. And like fine wine, the movie ages well upon reflection.

Full Review | Nov 16, 2019

A film that not only demands to be sampled but to be gulped down and savored like the vintage draft that it is.

Full Review | Original Score: 4/4 | Jun 5, 2019

Unfolding at a relaxed tempo, and unobtrusively edited, Sideways is a welcome throwback to 1970s Bob Rafelson and Jerry Schatzberg.

Full Review | Original Score: 5/5 | Apr 23, 2019

Where Payne's fondness for template narratives has started to become a problem, Sideways - as the title evinces - has much a more complex take on the possibility of catharsis

Full Review | Original Score: 5/5 | Nov 12, 2018

A beautiful little chamber dramedy about four sharply-drawn characters played with a very lovely mixture of nuance and showmanship.

Full Review | Original Score: 4/5 | Sep 27, 2017

Payne's most enjoyable movie since Election

Full Review | Original Score: B | May 24, 2013

Full Review | Apr 3, 2012

Payne does know how to capture two kinds of male menopause. But I can't say he ever surprised me.

Full Review | Feb 13, 2012

Excellent but explicit movie is not for kids.

Full Review | Original Score: 4/5 | Dec 28, 2010

"Sideways" is about wine aged to perfection sipped by men who've aged to mediocrity - softer, hornier versions of Walter and The Dude. But Miles's brutal honesty is its soul. He's annoyingly, depressingly out there, but never fraudulent.

Full Review | Original Score: 4/4 | Oct 1, 2010

Giamatti handily raises what could've been a pedestrian road trip romance into the stratosphere of a world-class character study

Full Review | Original Score: 3/4 | Sep 3, 2010

A very memorable slice of life.

Full Review | Apr 29, 2009

This wonderfully satisfying study in human nature is funny and sad and profoundly entertaining from start to finish.

Full Review | Oct 18, 2008

Sideways stays resolutely life-size. And that, in this age of hype and hyperventilation, may be the most radical thing about it.

Full Review | Nov 1, 2007

Sideways is the first of Payne's films in which we have the chance to really care for the characters; he reins in his harsh satire better than before.

Full Review | Original Score: B+ | Sep 7, 2007