The novelist Richard Yates, who died in 1992, was once called “a writer’s writer’s writer,” a witty epithet for a career spent at a maddening remove from the large public its owner craved. Yates made a splash with Revolutionary Road (1961), a novel praised for its unblinking depiction of suburban ennui. But the splash never rippled very far outward. Revolutionary Road remained the best known of Yates’s nine books, and his career bore the dreaded “nice reviews, no sales” stigma even as other writers, from Andre Dubus to Richard Ford (both students of his at the Iowa Writer’s Workshop), carried his brand of painstaking realism to far greater success.

Yates’s theme was failure; and his struggles—with the effects of alcohol and chain smoking, the indifference of the literary establishment, and his own deepening self-destructiveness and anger—were laid out in Blake Bailey’s 2003 biography, a study harrowing enough to make even the dreamiest would-be writer think twice about a life in art. After the author’s death, a group of admiring younger writers set out to resurrect his reputation and get his books back into print. The campaign brought Yates sufficiently far out into the light for people to discover him, including Kate Winslet, who read a script of Revolutionary Road and persuaded her husband, director Sam Mendes, to do it. The result is the kind of movie meant to impress by its lugubrious seriousness, and to offer a showcase for strenuously detailed, Oscar-grade performances.

Set in 1955, Revolutionary Road chronicles one turbulent year in the lives of Frank and April Wheeler, a couple who have moved with their two children out to the Connecticut suburbs from Manhattan, where Frank (Leonardo DiCaprio) does marketing for an IBM-like business-machines corporation. Both Wheelers feel destined for something better: she has thwarted acting ambitions; he scoffs at his own job and inveighs against “the hopeless emptiness” of their new milieu. At last, April (Winslet), sensing the cynicism enveloping them, dreams up a bold plan: leave their life of stifling conformity and move to Paris, where she’ll work as a secretary and Frank can discover what he really wants to do with himself.

Yates and his readers were close enough to the 1920s to share in a cultural memory of Paris as romantic symbol for writers and artists living the wild life of the Lost Generation. But for the Wheelers, setting Paris against the drab materialism of corporate commuter life is less about dissolution than dedication to a higher, “creative” purpose. In a flashback to the night they met, as new college grads, April asks Frank what he does, and when he begins describing his most recent job, she interrupts: “I don’t mean things like that. I mean what are you really interested in?”

There is something quaint in this solemn urge for authenticity—today, Frank and April would be Generation X neoyuppies whose carefully cultivated interests (travel, food, wine) would depend on their careers, not conflict with them. But as fuel for a novel or movie? A couple’s decision to go abroad in order to nurture the husband’s creativity makes an odd crux for drama. Then again, Revolutionary Road is a deceptively odd book, preoccupied in eccentric ways with masculinity. At every turn, April exhorts Frank to “be a man”; yet although Frank, like Yates himself, is a World War II veteran, manliness turns out to have nothing to do with physical courage, and everything to do with brilliance, conversational deftness, and sensitivity. In a second flashback to their courtship, we see Frank confiding his uncertainty about his future—“All I know is, I want to feel things”—and April responding with dreamy adoration: “I think you’re the most interesting person I’ve ever met.” In effect, Frank is going to Paris to become interesting, and thus to be the “man” his wife thought he was. Paris figures as a kind of intellectual and spiritual Viagra, something that will pump up Frank and save the Wheelers’ marriage.

Such a notion reveals how deeply performative was Yates’s view of human nature, and male nature especially. It’s fitting that Revolutionary Road begins with an embarrassing theatrical failure (April’s community troupe bombs in its debut), since essentially Yates was all about acting: the arduous challenge of impressing people by being (or rather appearing) confident, wise, and witty. In his brooding investigations of that avatar of the 1950s, the “outer-directed” man, Yates was ahead of his era. He depicted narcissism and narcissistic anxiety—and rage—at a time when you wouldn’t have heard such terms outside a psychoanalytic conference.

Mendes and his screenwriter, Justin Haythe, lift swaths of dialogue whole from Yates’s pages. But they’ve taken important steps to make these characters more likable, Frank in particular. Gone, for instance, is Frank’s encounter with the friend of a secretary he has exploited sexually; when the woman upbraids him, he dishes out an ugly misogynistic tongue-lashing. In Yates’s novel, despite being the primary point-of-view character, Frank is devious, selfish, vain, and cruel. DiCaprio’s Frank, on the other hand, is a semilikable person—a shallow but affable man who’s emotionally and intellectually overmatched by his wife.

And yet despite Mendes and Haythe’s attempts to nicen up the Wheelers and grab our sympathies, we’re left wondering, Why spend time with people this self-involved, miserable, and shallow? The popular TV series Mad Men, set in the same era and social milieu that the Wheelers inhabit, shares the same basic problem but responds with a furious effort of visual seduction and a playfulness that keeps tongue in cheek and gives the viewer a safe ironic distance. Revolutionary Road is Mad Men without the coy style and humor. It shares some of the iconic images—the rampant smoking, the womanizing and casual misogyny, the sea of men in suits and hats bobbing in luxurious slow motion through Grand Central Station. But one wonders, what does it mean, finally, to make dreamy visual poetry out of images of oppressive conformity?

In Road to Perdition (2002), Mendes showed the ability to distract us from weaknesses in his storytelling with beautiful pictures, and he does it again here. Revolutionary Road is full of lavish close-ups, and it is indeed diverting to study Kate Winslet’s face as it hosts protean emotions, then finally composes itself into a mask of grimly smiling spousal contempt. There is the usual capable work of Kathy Bates, here playing a meddling local Realtor, and a mesmerizing (and Oscar-nominated) turn by Michael Shannon as her deeply troubled grown son, a recent resident of a psychiatric institution, who befriends the Wheelers, admiring their critique of suburban meaninglessness, then turns on them ferociously when their alienation turns out to be a pose.

But even this powerful performance hints at something awry, and it can’t be blamed on the makers of this movie. The amount of loathing that swirls through Revolutionary Road is remarkable—not only marital loathing, but self-loathing, and, one senses, a strange and pervasive authorial loathing. Yates seemed to find a savage release in beating up on his characters. He interrogated them relentlessly, mercilessly exposing their secret fears and weaknesses, and skewering them on their own lies. It all finally repels, and Revolutionary Road, which I thought devastating at age twenty-three, now seems itself a part of the woefulness it portrays, its realism compromised by its jaundiced view of human nature.

In comparison I think of two other late, great masters of WASP suburban anomie from Yates’s generation, John Cheever and John Updike. Speaking of Cheever’s writing, Updike once said, with typical casual elegance, that “with all of his observations of men and women interacting, there is this sense of radiance, of something lovely.... He makes me feel as if I’m living in a world that is a kind of paradise, or could be, or was. It’s not a gift given to every writer. One trouble with many fiction writers is that we feel a drabness—the drabness of our everyday lives, and there’s no shift in gears somehow.”

Cheever understood two things profoundly, love and money. And it was the love in Cheever’s novels, Updike said, that “brings us...onto a plane where somehow things really do matter.” Yates, it seems, understood neither love nor money, or perhaps had too little of either to shift that gear and move his novels out of drabness. Meanwhile, seventeen years after his death, thanks to Kate Winslet’s hope for an Oscar, Revolutionary Road rises in the bestseller lists, selling more each week than it sold in Yates’s entire life. Would that he were here to enjoy success, and perhaps spend on his characters a little more grace.

Related: Celia Wren reviews Mad Men