Whit Stillman did not get the memo.

Or rather, he got it, scanned it with a frown, shoved it into the pocket of his J. Press khakis, and continued on his way, whistling a jaunty old tune (now at a slightly higher volume). The crumpled-up memorandum, widely circulated among American artists, includes the following:

1. Harvard students and other children of privilege are entitled, narcissistic wastrels.

2. The bourgeois ethos (responsibility, discretion, self-restraint, piety) is to la dolce vita (Dancing! Laughter! Spontaneity! Booze!) as tepid tap water is to luscious, golden olive oil; they can’t be mixed.

3. Optimism is for glazed-eyed rubes and tweenyboppers.

Stillman has spent his filmmaking career roguishly flouting these (actually unwritten) rules, and some others. His artful defiance has yielded a small but wonderful oeuvre comprising four films, all of which he wrote and directed: Metropolitan (1990), Barcelona (1994), The Last Days of Disco (1998), and now Damsels in Distress. Each of Stillman’s films follows a different group of privileged, highly educated, hyper-articulate young people just emerging from the chrysalis of adolescence. Their naked, earnest search for moral truth is oddly, delightfully interspersed with bouts of rich sensual indulgence. This combination is key to Stillman’s art: He is a nostalgist and an amateur moralist; but still, through it all, an exuberant, unembarrassed partisan of joie de vivre optimism.

Stillman’s focus on the American upper class, a group one of his characters terms the “Urban Haute Bourgeoisie” or “UHB,” has been the easy headline of his career. Stillman has been frequently called “the WASP Woody Allen,” and his first three films are sometimes called the “Yuppie Trilogy.” Some have recoiled at this focus, charging Stillman with snobbery (see rule one above). Evelyn Waugh, one of Stillman’s favorite novelists, tended to write about the English upper classes and answered similar criticism with a perennially sound rebuttal: “I reserve the right to deal with the kind of people I know best.” Stillman’s impeccably WASP lineage and Harvard education are reason enough to justify his focus on the UHB, but this focus also fills a gap in American art and life.

In his classic essay “Manners, Morals, and the Novel,” the great Jewish literary critic Lionel Trilling (another of Stillman’s favorite writers) wrote that most American novelists shared a crippling blind spot. They wanted to understand American society, but they could not reflect with any honesty on American manners because to do so would require engagement with the different manners of the different social classes, and in our theoretically horizontal society, there are no such differences. Or if there are, they are the result of showy affectation, and so a good egalitarian conscience requires that the manners of the upper classes be mocked and those of the lower classes bowdlerized and valorized.

Which is to say, neither of them can be honestly examined. Trilling argues that this failure is devastating for art that seeks to depict social realities because manners are a chief way in which a group’s values are embodied in day-to-day actions.

This blind spot is also bad for America’s self-understanding. We have not had a president without an Ivy League degree since 1989, and we won’t have another until at least 2017. Every one of our sitting Supreme Court justices went either to Harvard or Yale. East Coast elites really do run much of the country, and yet they serve as perpetual whipping boys for sanctimonious artists and Manichean populists on the left and right.

The upshot is that the milieu of our leaders remains woefully underexamined. There is much talk of a growing disconnect between upper and lower in America, and the artistic failure Trilling describes is not helping. Whit Stillman is one of the rare contemporary artists willing to deal sympathetically (if also critically and lightheartedly) with our untitled aristocracy. His humanization of an often-vilified demographic is an artistic virtue and, perhaps, a social service.

But I digress. And even if the preceding observations are accurate, they are somewhat out of place in an essay about Whit Stillman, because no one should mistake him for either a social realist or a moral crusader. At least not in any conventional sense. For reasons that only he could explain (and perhaps he couldn’t), Stillman has chosen to spend his artistic career writing dialogue for the young and searching. Authority figures are all but absent from his movies. Preachiness, and there is plenty of it, always comes leavened with a pinch of irony. Edification, when it does come, is stumbled upon by way of incessant questioning, foolish mistakes, or aesthetic transport—often some combination of the three.

Tom Townsend, the protagonist of Metropolitan, is a quintessential Stillman character. He is a serious, introspective Princeton undergrad affecting moral certainty, but deep down he is confused and dazzled by the wide world of young adulthood. He comes from a respectable old family but fancies himself a committed leftist, opposed to all manner of elitist, genteel traditions.

Almost against his wishes, he is swept up in the satiny, glittery rustle of the New York debutante season. On the first night of the season, he tells fellow ballgoers that he opposes such events on political grounds because, he explains, “I favor the socialist model developed by the 19th-century French social critic Charles Fourier.” Like so much of Stillman’s dialogue, the line is delivered in perfect innocent deadpan while Stillman winks impishly at his audience. But it turns out that all that champagne and dancing is serious business: Over the course of Metropolitan, Tom comes to understand and embrace the humanizing power of decorous, chivalric debutante society, finally becoming its quixotic defender.

Two decades earlier, with a few minor modifications, that was Whit Stillman. Halfway through a saturnine freshman year at Harvard, Stillman returned home to Washington and reluctantly attended his first debutante ball with a Students for a Democratic Society button pinned beneath his tuxedo lapel. As it happened, the dreamlike glamour of the deb season saved him from his own despair. By graduation he had traded his fashionable campus radicalism for unfashionable piquant nostalgia.

The Last Days of Disco, Stillman’s most recent film until Damsels, follows a group of recent college graduates in New York whose social triumphs and tortures center around an enchanting disco club, loosely modeled after Studio 54. The movie ends with the closing of the club, the professional defeat of most of the main characters, and a somewhat ironic soliloquy from one of them, arguing that disco may be dead but its spirit will live on in the hearts of those who loved it.

A somber mood reigns until, in the very final scene, a crowded New York subway car erupts into spontaneous dance (to the tune of “Love Train” by the O’Jays), which then fades into a faltering a cappella rendition of “Amazing Grace” as the credits roll. The old hymn is sung by Kate Beckinsale, whose character in the movie, Charlotte, is arguably the most despicable. Stillman here is hinting at a comprehensive, underlying moral structure—an almost sacramental connection between communal aesthetic rapture and higher redemption. The deep goodness that Stillman’s characters seek in their moralizing soliloquies is found, in part, by abandoning oneself to the beautiful. It is a moral schema with a rich pedigree, developed (though somewhat differently) in Waugh’s Brideshead Revisited.

With Damsels in Distress, Stillman has pushed the last scene of Disco even further, and in a different direction. Damsels concerns a group of beautiful young women led by Violet (Greta Gerwig) who take it as their mission to civilize the barbaric masculine hordes of their elite East Coast school, Seven Oaks College. They also operate a volunteer suicide prevention center. Their saving and civilizing missions are pursued by goofily aesthetic means: tap dancing lessons, perfume, good-smelling soap, and, of course, an impeccable fashion sense that evokes a sort of pastel-heavy postwar prep, slightly updated.

The girls mean it and, one suspects, at least in part, that Stillman means it, too. What Violet and her friends lack in self-awareness they make up for in perfectly enunciated term-paper disquisitions on how one ought to comport oneself. But for all their quixotic seriousness, the grand finale is boisterous and hilarious. It makes the “Love Train” scene seem like a tea party (the nonpolitical kind), and the viewer leaves the theater in a state of joyous disorientation. There is no “Amazing Grace” to tie the threads into a grand philosophical or theological proposition.

And yet, Damsels doesn’t feel like mere smarted-up escapism. None of Stillman’s films feels that way. He clearly admires the moral seriousness and altruism of the Seven Oaks girls, even if they are somewhat preposterous. Some enduring part of him longs to be a moralist, and, indeed, he is plainly suspicious of the bohemian ethos that exalts free love, total candor, and self-expression above all. Again, he is nostalgic for a steadier time, and a lingering sadness haunts his recollections. But here, now, given what we have to work with, Stillman’s goals are humble. He doesn’t advocate a wholesale return to the pre-Woodstock world; what good would that do? But what he does advocate, implicitly, is that we keep asking serious questions about how to live, live in accord with our best answers, and, from time to time, let our seriousness dissolve into the sumptuous, inarticulate joys of sensual reality.

That, Stillman seems to be saying, will be enough—and maybe, more than enough.

Ian Marcus Corbin is a writer in Boston.

Next Page