There’s a fascinating scene late in Sideways, Alexander Payne’s 2005 hit comedy about two old college pals on a disastrous road trip through California wine country. Payne’s antihero is Miles (Paul Giamatti), a failed novelist whose real passion is wine; a nebbishy introvert, he suddenly brims with confident expertise when conversation turns to Merlot and Pinot Noir. Wine snobbery provides a broad target for satire, and when Miles falls for a waitress, Maya, who shares his passion, Payne stages a seduction scene around wine talk, the two complimenting each other on their discriminating tastes before Maya—also an introvert—makes a tremulous play for intimacy: “Miles, can I ask you a personal question? Why are you so into Pinot?”

Payne and his screenwriter, Jim Taylor, weren’t simply mocking the Napa Weltanschauung. Yes, wine talk is precious but, according to Sideways, it’s also animated by the same impulses that animate all passions, including love. It was brilliant of Payne to make the most earnest moments of his movie hinge on the same material as its satiric moments—indeed, they’re the same moments. In that seduction scene, when Miles tells Maya about his ex-wife, whom he still loves, and sighs, “She has the best palate of any woman I’ve ever known,” his pretentiousness is being taken down but his emotion taken seriously. And when Maya in turn describes her own oenophile epiphanies, the camera closes in, her face burnished in golden light as she rhapsodizes over wine. The moment possesses a remarkable tonal ambivalence. Turn it this way and it’s wicked satire, a pastiche of platitudes. Turn it that way and it’s poetry.

Payne is America’s poet laureate of losers. Over thirty years, the writer-director has sheltered a menagerie of the bumbling, the henpecked, the ineffectual, the distressed, and the depressed. Payne lists both Italian neo-realism and American movies of the 1970s (he was born in 1961) as influences. But his films bear a stamp all his own. Their hallmark elements include a fondness for voiceovers; a reliance on music as an active arm of storytelling; a use of both professional actors and non-actors; a commitment to character-forward stories, adapted from novels, that emphasize place and character; and, above all, a balancing, or mingling, or juxtaposition, of disparate tones and intentions.

Payne’s movies exude ambiguity. They are comedies, but their humor ranges from heartfelt to harrowing, sometimes in baffling succession. In a perceptive 2013 essay in the New York Review of Books, Geoffrey O’Brien noted “a condition of permanent uncertainty” in Payne, “a mood that can move fluidly, with the slightest of accentuations, between farce and poignancy.” This mood movement is plotted via finely calibrated predicaments and responses, and executed, in his strongest films, with surgical care, resulting in “an authentic pathos,” as O’Brien wrote, “extracted with great skill from in between the constant jabbing notation of gesture and attitude and manners.” The dogged insistence on ambiguity has helped make Payne, in O’Brien’s judgment, “a true comic artist of the most deadly serious kind, for whom comedy is not deflection or distraction but a head-on gaze even into the direst circumstances.”

By the time Sideways snagged five Oscars and transformed Payne’s career, the director had been at it for fifteen years, experimenting with various admixtures of poignancy and farce. He won attention as a UCLA film student with his 1991 thesis work, The Passion of Martin, chronicling a young Manhattan photographer tormented by a sense of existential alienation—“doomed,” as he darkly confesses, “to a chaotic and senseless universe.” Passion introduced Payne’s enthusiasm for the voiceover deployed for ironic ends. Martin narrates a madcap capsule account of his miserable childhood, with images of birth—from the baby’s point of view—followed by a ferocious father snarling down into the crib, followed by the father’s death in a factory accident. “I was forced to come to terms with the emotional upset of his passing,” the voiceover earnestly informs us, as we watch ten-year-old Martin dumping an urn of ashes into the toilet. As for his mother, “the memory I cherish most is a conversation we had shortly before she died”—as Payne cuts to a garish closeup of the mother feeding, horselike, on a head of watercress and boasting that “it keeps my colon clean as a whistle—my stool, it’s like toothpaste!”

The dark farce continued with Citizen Ruth (1996), and the first of several films set in Payne’s hometown of Omaha. Laura Dern stars as Ruth, a homeless woman and addict who suffers an unwanted pregnancy and becomes a pawn in the abortion wars. Citizen Ruth starts with one of the bleakest opening sequences in American cinema. A woman submits to dismal, passionless sex in a filthy apartment, then, after being thrown out by her vile boyfriend, pathetically begs $20 from her angry brother, who is caring for her two neglected children. She immediately spends it on a can of spray paint that she huffs from a paper bag, passing out in a trash-strewn alley and awaking to be arrested by the cops. In jail, Ruth collapses on the floor of her cell, sobbing, “Oh God, please help me”—whereupon a troupe of Christian women appears, boisterously singing hymns and smiling insanely. The intrusion of clamorous facetiousness is wildly jarring. What seemed to be a realistic study of American degradation—Winter’s Bone, say—suddenly becomes Christopher Guest. Wait, you think, this is comedy?

As in Martin, Payne’s humor turns on an implicit view of humans as animals. Ruth is the protagonist, yet she seems to have no interiority, merely a basic drive to avoid pain and fulfill needs. When the nine-year-old boy in her Christian host family shows her his models, her eye zeroes in on the glue; and when pro-choice activists offer to pay for her abortion, and pro-life Christians make a counteroffer for her to keep the baby, she exults in greedy glee at the impending bidding war. Roger Ebert, describing Citizen Ruth as “a gallery of sharp-edged satiric portraits,” praised Payne’s “courage” in making Ruth “an unredeemed dopehead whose only instinct is to go for the cash,” while noting that “we may yearn for someone to cheer for, instead of against.”

It’s not a yearning Payne was at all inclined to gratify early in his career. Both Citizen Ruth and The Passion of Martin emit a scattershot vehemence. Their take-no-prisoners satire is enforced via startling disjunctions among voiceover, image, and music. Cheesy sitcom-style music adorns some of the most degrading moments in Ruth’s ordeal; The Passion of Martin ends, brutally, with a closeup of a hospitalized woman in a vegetative state, a ventilator punctuating the soundtrack’s jaunty version of “The First Time Ever I Saw Your Face.” And Martin’s recollection “as I said goodbye to Father for the last time, I was moved by the example of his dignity in death” is voiced over the image of Father’s ashes swirling down the vortex of the toilet. Both films suggest a young director gobsmacked by the gap between lofty human aspiration and base human reality, and responding with sardonic laughter.

With these two apprentice efforts behind him, Payne went on to make three movies that form the core of his achievement. Approaching forty, the director zeroed in on what would become his abiding subject—the varieties, and indignities, of midlife male failure—and began assembling what New Yorker critic Anthony Lane has wittily called his collection of beached American males.

Payne’s sense of something inherently rueful in American maleness is displayed in a recurring, highly enjoyable motif: the ridiculousness of men running. The Everyman played twice now in Payne’s movies by Paul Giamatti is an obvious physical shlub. But even George Clooney moves like a doofus when processed through Payne’s nerd machine. As he runs down his driveway in sandals in The Descendants (2011), his stumpy, uncomfortable gait makes him look like a man desperate to get to the bathroom. There’s usually some form of sexual urgency involved when men run in Payne (Clooney has just discovered that his wife has had an affair), and it does not conduce to gracefulness. In About Schmidt we see Jack Nicholson half-skulking, half-hobbling across a trailer park, fleeing the outraged woman he has just made an awkward pass at. Best of all is Matthew Broderick’s beleaguered teacher in Election, Mr. M, who hastens in a half-trot through the halls of school, trying inconspicuously to rush through his end-of-day routine and get to the motel where he plans to meet his new lover. Both sneaky and prim, his mincing run suggests sexual anticipation overlaid with caution and guilt.

Taking on the midlife nerd had a beneficial effect on Payne’s moviemaking, softening his comedy and enabling a new quality of fond humiliation. That’s the signature tone of Election (1999) and Sideways (2005), both taking up the romantic travails of two milquetoast schoolteachers. Payne was an English major in college and has frequently extolled the novel’s emphasis on character, its way of being “all about the details.” In Sideways, we see Miles reading while eating alone in an empty Chinese restaurant, reading while on the toilet in his cluttered apartment, even reading while he drives. In Election, Mr. M attempts to put his lunchbox in the faculty-room fridge, only to find it crammed to overflowing with old Chinese takeout, a half-eaten apple, a Styrofoam bowl of melted dessert. The mass of men eat lunches of quiet desperation. Election and Sideways show the slashing quality of Payne’s irony yielding to a sly wit that gives his pair of nebbishes a running chance at gaining our sympathy. Remember the indelible scene of an enraged Miles wreaking havoc at a wine tasting? The unfolding disasters that beset Giamatti’s and Broderick’s hapless losers track the kind of bad dream we’re all prone to. We are laughing at them, yes—even as a small voice whispers, “That could be me.”

These films revealed Payne not only finding new filmmaking tools but using the ones already in his toolkit more effectively. Election is a masterpiece of editing: freeze-frame shots of one character’s face while another character provides voiced-over commentary; scrapbook montages of star student Tracy Flick’s accomplishments; a fast-action compilation of shots of Mr. M in a dozen different shirts and ties, drawing the same civics diagram on the board, year after year. The voiceover commentaries that were put to jokey and sophomoric purposes in The Passion of Martin serve more subtle and doleful aims, like denial. “After nine years of marriage we were closer than ever,” Mr. M comments cheerfully—as we watch him and his wife eating a glum and wordless dinner.

Both films also make deft use of music. In a 2005 interview with LA Times critic Kenneth Turan, Payne noted the “huge” importance of music in his movies, not merely for “atmospheric” purposes, but to further characterization. The music in Sideways helps steer the film’s satirical collision between the good life and two men pathetically incapable of living it. Big stretches of the movie look like wine commercials, with couples laughing around vineyard dinner tables and Rolfe Kent’s sunny soundtrack bubbling ironically along. Its sixties Italian jazz is the quintessence of carefree, and we keep expecting Marcello Mastroianni—but what we get instead is the angst-ridden Miles and his pal Jack, a pathological philanderer. Election, for its part, deploys everything from French chansons to lounge music to Ennio Morricone’s epic Western themes to the taunting coda of Mandy Barrett’s sassy country tease, “If You’ll Be the Teacher”—all of it making for a colorful potpourri that highlights by contrast the monochrome drabness of Mr. M’s life.

Payne followed Sideways with The Descendants (2011), in which a Hawaii lawyer and family man copes with widowhood, an obstreperous teen daughter, and a fractious crew of relatives disputing an inheritance. Then, dramatically shifting gears, he made Nebraska (2013), viewed by many as his greatest film. A father-son road movie shot in black and white, it stars Bruce Dern as Woody, a cantankerous eighty-year-old former auto mechanic in Billings, Montana, who receives a promotional sweepstakes certificate in the mail. Convinced that he’s won a million dollars, Woody is hellbent on getting to the sweepstakes office in Lincoln, Nebraska, to collect it; and since he no longer drives, he sets out on foot—again and again, his wife or son having to haul him back each time.

With Nebraska, Payne seemed to push back against a certain feel-goodism in his previous three films, starting with the setting—the verdant warmth of California and Hawaii replaced by the starkness of the Western plains. The movie opens with Woody shambling along a major road outside Billings, traffic roaring by, against a bleak panorama of train yards, factories, and disused industrial spaces. “Where’d they find him this time?” his son asks, fielding a distressed phone call from his mother. “I don’t know what I’m gonna do with him,” she sighs wearily, as if Woody were an incorrigible dog. The setup echoes the theme of the human as animal; like Ruth in Citizen Ruth, Woody is fixated on getting his treat. But Payne has deepened this conception. Woody in his maddening singlemindedness seems to possess some tight, coiled secret that compels him. The state of Nebraska is his version of Gatsby’s green light; whatever it symbolizes to him, he can’t let it go, and part of the film’s draw is the incremental process by which we begin to see inside him.

Payne has described his conception of a film as an interplay of opposing forces, ingredients that a director “pulls out like taffy.” In Nebraska, the forces in tension are aimlessness and obsessiveness. The plot is a classic shaggy-dog story that begins when Woody’s younger son David (Will Forte) reluctantly agrees to drive him to Nebraska. With certain disappointment looming at its end, there’s no hurry, and trip and film both live in the detours. A stop in Woody’s hometown, a visit to relatives, and the gentle probing of his son all elicit his cranky fixation on old grudges and debts—such as an air compressor that his ancient nemesis Ed (a casually brutal Stacy Keach, in a brilliant turn) borrowed from him long ago and never returned.

The movie is a masterpiece of the laconic, both visually and in its sparse script. Black and white closeups of faces evoke a Dorothea Lange–like rural stoicism, and a sepulchral pall hovers over the dying Main Street of a Nebraska town—dreamy music playing, with typical Payne dissonance, as David and Woody trudge past shuttered storefronts. There’s a sense of bleak futility against the implacable obliterations of time. “Did you ever want to farm like your dad?” David asks as the two stand outside the ruined farmhouse where Woody grew up.  “I don’t remember,” Woody says, distantly. “And it doesn’t matter.”

Yet amid all the dourness and severity come moments of authentic mirth. “Look at him, he’s useless,” Woody’s wife complains vehemently at one point. “His mother spoiled him.” His mother spoiled him? The man is eighty! In one rollicking scene, David and his older brother Ross (Bob Odenkirk) conspire to steal the air compressor back, driving their parents out to Ed’s house, where they ransack his barn and abscond with the machine. Only a half mile down the road, his sons loudly triumphant, does Woody offer a simple remark. “That’s not my compressor. Looks nothing like it.” Wrong house, wrong barn. In another scene, Woody and David search along the railroad tracks for Woody’s teeth, which fell out of his mouth when he stumbled back drunk from a tavern the night before, and seemingly find someone else’s.  “I oughta know my own teeth,” Woody grumps.

Nebraska is the fiercest of Payne’s movies. And in a surprising way, it’s the funniest and the most forgiving. It strikes me as the director’s most complete realization of his original vision; you have the feeling that it drew on all parts of him and excluded none. Halfway through, it is hard to envision any kind of redemption materializing amid its panorama of failure and ruin, and yet it comes nonetheless, however muted—in the gift of a used pickup truck from his son, and the bestowal, by his ever-irritable and long-suffering wife, of a single tender kiss.

Payne’s new film, The Holdovers, is set in the winter of 1970 at a wealthy Massachusetts prep school, Barton Academy, where a handful of boys unable to go home for Christmas break must hunker down over the holiday, with one faculty member as their minder—Mr. Hunham (Paul Giamatti), a pompous history teacher notorious for meanness. One day in, four of the five boys are bailed out by a wealthy dad who arrives in a helicopter, leaving only Hunham, along with a smart but troubled seventeen-year-old named Angus (Dominic Sessa) and the school cook, Mary (Da’Vine Joy Randolph), a Black woman whose son was recently killed in Vietnam. Will this unlikely trio get through the holiday without driving each other crazy?

Reviewers have deemed The Holdovers an instant Christmas classic—to its creator’s chagrin. When a Vanity Fair interviewer burbled about how “everyone I know says how light and cozy they felt coming out of the theater,” Payne practically lopped his head off. “That nauseates me a little bit,” he retorted, disavowing any intention of making “a cozy movie or a warm hug, or putting on a sweater on a cold day and drinking hot cocoa.”

Yet you can see why someone might have that warm-hug, hot-cocoa feeling about The Holdovers. Opening with a shot of a New England village in picture-postcard wintry enchantment, and featuring a Christmas dinner at which Hunham, like Charlie Brown, fetches a lopsided tree to decorate the dining room, the movie offers warm fuzzies previously unimaginable in Payne. This is also the first time the director has set a film in the past, and his movie is stocked with vintage artifacts, from the transistor radio playing “Knock Three Times” by Tony Orlando and Dawn right down to the period-piece Preparation H tube in Hunham’s bathroom. In fact, even before the first images land, we are subliminally prepped for nostalgia. The first thing we see is the rating panel—and it’s the old sky-blue one, with the R in the white ribbon across the bottom. Remember that? As in the old days, there’s scratchy static as the sound comes up, and if you look closely alongside the MPAA logo, you’ll see “Copyright MCMLXXI.” Payne’s conceit is that The Holdovers isn’t just a film about 1970, but one made in 1970. The conceit continues via scenes shot in ways that evoke TV and movies of the era—reverse zoom cuts, for instance, or slow dissolves, or the film’s long, stationary closing shot of a car disappearing down a country road as the music comes up and the credits roll. Nostalgia is built into the bones of The Holdovers.

Then there’s the Grinch theme. Unlike the milquetoast teachers in Sideways and Election, Mr. Hunham has a career grounded in an era of unquestioned male authority, and he wields that authority with cruel glee. “Lazy, vulgar, rancid little Philistines,” he mutters, happily, as he sits at his desk, smoking his pipe and grading their exams. The next day he saunters into class, whistling “Ride of the Valkyries” as he hands them their dismal grades. “I see that many of you are shocked,” he archly intones. “I, however, am not, because I have had the misfortune of teaching you this semester.” Hunham even looks like the Grinch. “Try to be human,” the headmaster pleads with him as the holiday break begins. “It’s Christmas.” And so we wait to learn how and when, exactly, the Grinch’s heart will go from being two sizes too small, to busting through the heart-o-meter.

The process tracks larger evolutions underlying the story. Set in the winter of 1970–71, the film captures a school frozen in formality as a great storm of change approaches. Portraits of Barton’s headmasters—all male, all white—loom over a faculty dining table that looks like it could be from 1950, even as the students are beginning to exhibit an unruliness osmosed from the great world beyond, evidenced in their shaggy dishevelment, their pot smoking, profanity, and raucous music. Somewhere out there, Kent State is happening, and Stonewall, and women’s lib, and Vietnam; but you’d hardly know it from the stately campus, its stone buildings like mausoleums in the snow, or from teachers who call their charges “Mr.” and demand absolute deference. David Hemingson’s script captures the last moment in America when rote obedience to rules was the norm. In a restaurant in town, a waitress informs Hunham and Mary that they can’t order cherries jubilee for Angus, since the dessert contains brandy. When Hunham points out that the alcohol will burn away, the woman smiles with prim complacency. “Those are the rules—sorry.”

From this starting point, Payne and Hemingson work to break down rules and proprieties, with the three holdovers acting as a miniature simulacrum of the society beyond. Sharing their meals and evenings together, and with whisky as a lubricant (Mary and Hunham both like Jim Beam), the two adults watch TV (The Newlywed Game!) and discuss their lives and losses, as Angus sits behind, reading a book and listening in. Plainspoken Mary treats Hunham with a kind of scoffing affection; when Hunham recalls her late son, Curtis, who went to Barton and took his class, she interrupts: “He said you were an asshole.” There is no intent to wound, just to speak honestly, and her candor catalyzes truth-telling within the group, so that by the end of an impromptu road trip that the three take to Boston deep-seated hurts have been revealed all around: Mary’s insurmountable grief over her son; Angus’s broken family, afflicted by mental illness and divorce; and a long-buried shame in Hunham’s past.

A middle-aged male teacher committing mistakes (several school rules are broken on the Boston road trip) and having to face the music isn’t exactly new terrain for Payne. Yet The Holdovers feels different. It’s a more serene movie than any the director has made before. The film’s opening sequence, with students enjoying the campus in its sparkly winter loveliness, is set to folk singer Damien Jurado’s “Silver Joy,” with its mellow guitar strum and comforting lyrics (“Lay your troubles on the ground / No need to worry about them now.”) In a typical Payne film, you’d expect such music to comment ironically on some scene of perplexity. Not here. His tools of dissonance—the ironic voiceovers, the madcap music—have been put aside, for now at least.

This is Payne’s most acting-centered film to date. The director is often referred to as actor-friendly, yet in previous films, when his actors have excelled, it has been a one-note kind of excellence: Reese Witherspoon’s furious ambition as Tracy Flick in Election, for instance, or the cantankerous stubbornness of Bruce Dern’s Woody. The Holdovers aims at more expansiveness. There’s a remarkably moving scene at a Christmas party in town, hosted by the school’s secretary, where a drunk Mary puts an Artie Shaw album on the record player. “Curtis loved Artie Shaw,” she murmurs. “We used to dance to it. What teenager loves Artie Shaw?” When someone requests different music, she explodes (“Don’t touch that goddamn record!”), then sinks back on the sofa. Cinematographer Eigil Bryld’s camera moves in for a full-screen closeup, and we watch contending emotions—dreamy recollection, grief, pleasure, anger—play in protean fashion across Mary’s face. This protean quality is new to Payne. In the Kenneth Turan interview, the director commented that actors “have to be the appropriate vessels for the tone” that screenwriter and director conceive in a scene. In The Holdovers, one senses the actors actually discovering things for Payne, rather than just executing his commands.

As for Paul Giamatti’s Hunham, his de-Grinchification follows a carefully charted course, as our response to him grows ever more solicitous. Payne is a genius at locating the comedy in loneliness, and Hunham is his most affecting portrait to date, a man so habituated to his own company that he has a mantra he recites when, falling drunkenly into bed, he farts: “Monet, Manet, PiCASso!” Like other men in Payne’s movies, he seems to have lost all limberness; in his morning stretches, the only thing that seems to move are his arms. When he picks up a football half buried in the snow and throws it, it is the single worst football throw ever recorded in cinema. He’s further ossified by his own incorrigible pedantry. We slowly realize that his habit of delivering a lecture isn’t just how he wields authority, but also how he parries attempts at human connection. For example, when Miss Crane kisses him at the Christmas party, pointing to the mistletoe overhead, Hunham responds by noting that “Aeneas carried mistletoe with him when he descended into Hades in search of his father.”

The film’s serenity arises from the aftermath of pent-up griefs and dreads being released, and truths being aired and absorbed. On the Boston road trip, Angus informs Hunham that “most of the kids pretty much hate you…. You know that, right?” The jagged moment is followed by a sweet scene of Hunham taking Angus skating, Angus sliding awkwardly around the rink and smiling over to where Hunham stands watching, like a little kid beaming at his dad. By film’s end, Hunham has been ejected from the school where he has spent most of his life, but that’s okay, since in the process he has been freed from the burden of what we would nowadays call toxic masculinity, and introduced to intimacy, candor, and human connection. Alexander Payne isn’t a director you would normally think of as therapeutic. Yet here he is. His film’s penultimate scene unfolds on New Year’s Eve, the three holdovers joined by the school custodian, Danny, all watching Guy Lombardo, then lighting off a firecracker—in the kitchen—at midnight, welcoming in 1971 with a bang. As they embrace and shake hands, the camera effects a gradual fade, in the process tracking very slowly back through the living room and then through an outside window, double-framing the revelers. I defy anyone to watch that moment, with its tableau of friendship and celebration, and not feel at least a little warm and cozy.

Payne is in his sixties now, and The Holdovers shows a filmmaker who has learned a few new tricks and isn’t quite the same old dog. This isn’t his best movie; it isn’t his funniest, or shrewdest, or edgiest, or even his most interesting. But it is the subtlest and mellowest of his films, and also the nicest. He might not like that, but it’s true.