Not long ago, amid a thirteen-year gap in activity punctuated only by vanishing wisps of project rumors, it seemed that there might be only three Whit Stillman films. Today, six years into a second phase of productivity, including two films, a novelization, and an Amazon series, such fears are a thing of the past. And yet, even if he had never been heard from again, that initial Stillman trilogy would be something no one could soon forget.

The “Doomed Bourgeois in Love Trilogy” is not exactly a title as pithy as “Three Colors” or “The Dollars Trilogy.” But it encapsulates the character of Stillman’s three 1990s films, in their wistful, fatalistic, and loquacious qualities. They are also, in a very real sense, timeless. Indeed, Stillman’s work generally—excepting his latest film, Love and Friendship, a detailed Jane Austen adaptation—seem always out of place, projecting a disregard for both their intended settings and the points at which they were filmed, with a sensibility out of joint with the contemporary era.

Stillman’s first film, Metropolitan (1990), was derived loosely from the plot of Austen’s Mansfield Park, while Love and Friendship, an adaptation of her novella Lady Susan, prompted some critics, not unreasonably, to suggest that Stillman had at last found his natural era. And yet the idea that Stillman is a natural Georgian playwright who suffered the misfortune of too late a birth is far too simple.  His sensibility draws upon a number of elements found singly in the work of other directors and writers but in combination nowhere else. Most of these elements aren’t exactly recent but few of them are decidedly old. There is Austen, Shakespeare, and Balzac, but also the active imprint of Fred Astaire comedies, J.D. Salinger, Woody Allen, Jim Jarmusch, and of course disco.

Though certainly a contemporary filmmaker and not in any sense a stranded nostalgist, Stillman nevertheless displays qualities that, while once common, are now so rare that they put him in stark relief against nearly all of his contemporaries. Perhaps most pronounced is his distinctive affection for his uniformly well-born characters. If revulsion for bourgeois hypocrisy seems an obligatory quality in American independent filmmaking these days, Stillman will have none of it. He offers instead a gentle satire of his characters’ foibles combined with a frank sympathy for their principles. While quite natural in Austen novels and RKO comedies of the 1930s and ’40s, this is rare today. Thus is it all the more striking that Stillman continues to receive critical acclaim from disparate publications and institutions, from a Vanity Fair photo spread for the 25th anniversary of Metropolitan to a volume of effusive essays from the Intercollegiate Studies Institute.

A former editor for The American Spectator who makes films extolling virtue and patriotism logically wouldn’t receive praise from Wes Anderson (Rushmore, The Royal Tenenbaums) or Lena Dunham (HBO’s Girls) and wouldn’t be widely compared to Eric Rohmer. Yet Stillman receives praise from these people, which reflects the extent to which his work stands out in today’s movie world.

A year after Metropolitan was nominated for an Academy Award for Best Original Screenplay in 1990, nominations for that distinction went to writers of very different scripts: Thelma and Louise and Boyz n the Hood. Neither featured anything approaching this Metropolitan line: “So many things which were better in the past have been abandoned for supposed convenience.”

Metropolitan

Metropolitan is often thought of as a black-tailed artifact of the 1980s adrift on the rising seas of 1990s Miramax, and yet its anachronisms were more complicated than that. While it borrows its attire from the 1980s, it gets its inspiration from the debutante ball culture of the 1960s, its spirit from 1930s cinema, and its story from Jane Austen of circa 1814.

There was a distinct autobiographical thread in this picture, derived from Stillman’s rarefied circles, if no longer rarefied bank account. While descended from James Jewett Stillman, board chairman of National City Bank and one of America’s richest men at the turn of the last century, the family fortune didn’t last, and Stillman spent most of his Manhattan childhood living with his divorced mother in circumstances considerably below those of his rich ancestor, not to mention his contemporaries at school. One winter during an unhappy first year at Harvard he fell in with the fading debutante circuit of Washington, D.C., and this experience serves as a setting for Metropolitan.

The plot is simple: a skeptical outsider, Tom, living in reduced means with, yes, his divorced mother, finds himself thrown in with a circuit of Manhattan friends during the pre-Christmas week of debutante balls. Gradually he finds himself won over by this outwardly stuffy group, which welcomes him due in part to an “escort shortage”—parlance of the time for an insufficiency of male companions to attend the holiday galas. Enter Tom, endearingly earnest in his avowed socialism. His new friends, making up the Salingerian Sally Fowler Rat Pack, soon prove more appealing than imagined—particularly one debutante, Audrey Rouget.

The rat pack, to be clear, is somewhat ridiculous, but its members are neither vapid nor psychopathic. One member, Charlie, who does much of the more elaborate theorizing, observes that he watched Bunuel’s Discreet Charm of the Bourgeoisie and was disappointed to find that the characters in the film were not remotely charming. But Tom’s new circle, as drawn by Stillman, is charming—even Nick Smith, the prickliest member but also particularly welcoming of Tom.

We soon discover a theme that runs through nearly all of Stillman’s work—that even in the most rarefied of societies, the participants are living on borrowed time. A greater acquaintance with these societies reveals not their strength but their fragility: Connections of value and of shared interest are fraught with risk. Though sufficiently well-off by most standards, these young adults are haunted by a sense that their accomplishments inevitably will pale in comparison to those of their forebears.

This is a quality accentuated in Metropolitan in that its focus isn’t just on affluent youths lounging in their parents’ Upper East Side living rooms. It focuses more broadly on a community surrounding a social ritual, the debutante ball, that seems today antediluvian and was clearly in decline, certainly in the year of the film’s release but even in the very years Stillman was experiencing this milieu some 45 years ago. The movie’s characters form a group centered on a dying tradition, one that orients them toward a very real sense of propriety and virtue. When Tom jilts Audrey one evening in pursuit of a former flame, he receives direct rebukes; the community isn’t simply a discretionary congerie held together so long as nobody is bored; it harbors a very real sense of order and propriety.

We recognize this to a large extent because the rat pack is threatened by an actual rat, an unusually one-dimensional villain in the Stillman universe—a titled baron, Rick Von Sloneker, “something of a stock literary character, an 18th century scoundrel,” as Stillman describes him, one against whom the bounds of the group are defined. Sloneker is a modern rake, a lothario whose indiscretions, however, aren’t much held against him, though Rick Smith is quick to issue dire warnings about him.

Stillman once declared it “delightful” to be called “moralistic” by the provocative novelist and screenwriter Bret Easton Ellis. Moralism is the one quality in the upper classes unbearable to their critics, who regard it as inevitably fraudulent. Stillman paints a world in which moral codes are important—not, as critics often impute, in contrast to the barbarous lower classes, but in contrast to Von Sloneker’s very real world of entirely craven wealth.

In the movie, Charlie opines that social snobbery and social distinctions had become essentially taboo in the United States; but moralistic distinctions remained. It’s one way he and his friends could differentiate themselves from the Donald Trumps of the world. As Richard Brody wrote in The New Yorker, “‘Metropolitan’ evokes the responsibility that social position implies, even if only for the healthy and constructive maintenance of the society in which position is enjoyed.”

Stillman’s interest in tradition and social order conjoins a much more enduring interest, one that is the principal concern of nearly all of his films—the social dynamics of the young, the ineffable question of just what sustains collective friendship. This is partly a question of larger moral codes mapped onto a congerie but also partly the inevitable and yet still often poignant circumstance of the need to move on to different things or different locations. The movie itself depicts the gradual dissolution of the group as it scatters naturally after the unifying purpose of debutante week. This is of course entirely normal in narrative terms, but also symbolic, representing the rending of social bonds and traditions in the transition from the 1960s to the 1970s.

As Stillman observed from his own youth, “Groups can become so ferocious with someone who breaks their rules.” Nevertheless, there is a rueful quality to most dissolutions. “We can’t just be getting together with the same people every night for the rest of our lives.”

The film’s interest is not the didactic elaboration of moral codes but the gentle suggestion of their value and an evocation of the fact that they are not invariably a tissue of lies. And this is distilled with sparkling dialogue and beguiling humor. For example:

Audrey Rouget: What Jane Austen novels have you read?

Tom Townsend: None. I don’t read novels. I prefer good literary criticism. That way you get both the novelists’ ideas as well as the critics’ thinking. With fiction I can never forget that none of it really happened, that it’s all just made up by the author.

Barcelona

Stillman’s next film, which germinated in his own experiences working in Spain for a Spanish film company, concerns two Americans in Barcelona, played by Chris Eigeman and Taylor Nichols. It’s an unusual genre mix for a Stillman film, a romantic comedy leavened by the real threat of deadly violence.

In Barcelona (1994), Eigeman is a naval officer and Nichols a businessman, two of the most square of occupations, but in typical form any expectation of boors abroad is rapidly undermined: they may hold some air of Jamesian innocence, but they are not fools and they are certainly not Ugly Americans. The film pokes fun at them, for sure; early on Nichols likens one street to “The Michigan Avenue of Barcelona” and moments later says of another, “Actually it’s more like Michigan Avenue.” And yet they’re never stock rubes, nor do they fulfill the frequent precondition for a sympathetic American abroad of loathing or escaping his own society. Ted wasn’t fleeing his business work but embraces it, reading Dale Carnegie and self-improvement manuals. Eigeman, as naval officer and patriot, “actually believes that stuff.” Stillman brings us a cosmopolitanism that doesn’t pretend that appreciation of other societies must imply a distaste for the United States.

Eigeman arrives at his cousin’s Barcelona apartment for an indefinite stay and a healthy amount of sponging, and their main quest is female companionship, forays into the charming world of Barcelona bars, jazz, and a variety of girls that include an enchanting Mira Sorvino.

All this unfolds against a backdrop of general anti-Americanism in Spain and actual violence stemming from a conviction among many Spanish that Cold War tensions were the solitary fault of the United States. A bombing occurs, inspired by a real-life bomb at an American consulate. Stillman is particularly deft in skewering the half-informed European portraits of America and Americans. One character, Ramon, a left-wing journalist, is a tone-perfect send-up of quack authorities on American perfidy. He goes on at length on the conspiratorial activities of a nefarious American institution he calls the “AFL-CIA.” This disconnection is reflected in an exchange between the Taylor Nichols character, Ted, and his Spanish antagonist.

Ted: In the U.S. government’s view, which I’m not in any way endorsing, the U.S. policy is… Maybe an analogy will help. Take these ants [pointing to ants on the ground]. In the U.S. view, a small group, or cadre, of fierce red ants have taken power and are oppressing the black ant majority. Now, the stated U.S. policy is to aid those black ants opposing the red ants, in hopes of restoring democracy and to impede the red ants from assisting their red ant comrades in neighboring ant colonies.

Ramon: That is the clearest and most disgusting description of U.S. policy I’ve ever heard. The Third World is just a lot of ants to you!

Another participant: Those are people dying, not ants!

Ted: No, I don’t think you understand. I was reducing everything to ant scale. The U.S. included – an ant White House, an ant CIA, an ant Congress, an ant Pentagon.

Ramon: Secret ant landing strips, illegally established on foreign soil!

Fred (Eigeman): Where are the red ants?

Ted: There.

Fred: Smashes the red ants with a rock.

It isn’t all just fun, though. Seriousness intrudes after Ramon identifies Fred as a CIA operative, and he is shot. A lengthy sequence of recuperation in a hospital lends gravity to this tale, one that still concludes on a happy note. It is at times hilarious, with physical comedy added to the usual verbal marvels. A particularly funny scene unfolds when Ted is caught jitterbugging to Glenn Miller while reading the Bible. “What is this?’’ asks Fred, walking in on him. “Some strange Glenn Miller-based religious ceremony?” Reply: “No, I’m Presbyterian.” This is difficult to imagine on any level from another filmmaker. Here’s a Bible reading that’s not dour or ascetic, which is a silly thing to be caught doing, but not actually to be doing.

Barcelona also is the most explicitly Shakespearian of Stillman’s plots, closing with a double wedding and an outdoor celebration, at which these willful expatriates enjoy an old-fashioned American hamburger.

The Last Days of Disco

In his third movie (1998) Stillman returned home and to his interest in group dynamics, as drawn once again from his own life. The story is told through the perspectives of two female characters, Alice and Charlotte, played by Chloe Sevigny and Kate Beckinsale. They are readers for a publishing house, and, like Tom in Metropolitan or Stillman in life, they are of less ample means than those around them. Indeed, they are barely scraping by in Manhattan—but fortunate enough to be regularly scraping into the city’s most prominent disco club.

The club, modeled on Studio 54, is inspired by Stillman’s own memories of that place, which he accessed through his connection with a crowd associated with Diane Von Furstenberg’s husband. His portrait of the era is about as far from Saturday Night Fever as you can get. He commented in one interview, “The disco era, whose erstwhile existence, from almost the moment it ended, has seemed to embarrass most Americans more than Watergate.” Not him. He recalls the era as a unitary moment in which discos were highly welcoming to outsiders (once you managed to get past the bouncer), an easy place to meet people in ways that did not exist previously and has not existed since.

The disco community included revelers of disparate incomes and appearance, some of them as flamboyant as popular disco imagery but most, in a point Stillman stresses as historically accurate, far more average-looking than legend would suggest.

These are what might be called proto-yuppies. Thus do we find ourselves back in territory, like Metropolitan’s focus on preppies, where social designation becomes a slur and where a descriptor that flourishes for a while seems to disappear almost without a trace. Stillman is endlessly fascinated with such classifications and their uses, and he’s more than happy to portray the merits of a demographic that is broadly despised. As one character (played again by Eigeman), clearly a yuppie, says, “No one says, ‘I am a yuppie,’ it’s always the other guy who’s a yuppie.” He elaborates, “Yuppie stands for ‘young upwardly mobile professional.’ Nightclub flunkie is not a professional category. I wish we were yuppies. Young. Upwardly mobile. Professional. Those are good things, not bad things.”

Stillman is aware of the faint-to-considerable ridiculousness of the statements of his characters, who themselves are often self-aware, but he also makes them convincing. One monologue, from a disco aficionado waxing eloquent on the phenomenon as it fades into the past, illustrates Stillman’s deft handling of such subtleties:

Disco will never be over. It will always live in our minds and hearts. Something like this that was this big, and this important, and this great, will never die. Oh, for a few years, maybe many years, it will be considered passe and ridiculous. It will be misrepresented, caricatured and sneered at, or worse, completely ignored. People will laugh about John Travolta, Olivia Newton John, white polyester suits and platform shoes and going like this! [Mimics Saturday Night Fever pose] But we had nothing to do with those things and still loved disco. Those who didn’t understand will never understand. Disco was much more, and much better than all that. Disco was too great and too much fun to be gone forever. It has got to come back someday. I just hope it will be in our own lifetimes.

The disco here is a formalization of group boundaries: while social ostracism may police the boundaries of other group sociability, here a bouncer does. The contours of the plot follow romantic assignations and turmoil, book publishing (a fake Dalai Lama memoir), and a much more terminal threat to general conviviality with the closing of the disco club.

There are romances sprung from this, and these are favored, but if, as in Metropolitan, a final romance is the genuinely happy conclusion, Stillman’s principal and repeat narrative interest in those days that precede this settling is undeniable. As Eigeman’s character comments, “Getting seriously involved with someone really just means ruining your nightlife.” And, if that might actually be worth it, Stillman seems to want us to ponder the tradeoff.

Later Work

After more than a decade of misbegotten projects (and a sly cartoonish cameo as a disco creep dancing to Talking Heads’ Psycho Killer in The Imperialists Are Still Alive) he returned with two films and an Amazon pilot-and-future-series. Damsels in Distress (2011) turned to an even closer focus on youth, a movie about college life, although it certainly doesn’t resemble college comedies of this or any other era. It centers on a group of females running a suicide prevention group who, in characteristic Stillman form, take in a newcomer. The story features one avowed Cathar, one invented dance, no actual suicides, and a wealth of contrarian sentiment. The fraternities are not Greek but Roman, and their members are defended, along with the value of, for example, cliches. As one character explains, “I love cliches and hackneyed expressions of every kind, because they’re largely true. The thousands of such cliches and hackneyed expressions that our language has bequeathed us are a strong treasure trove of human insight and knowledge.”

His next project was a series pilot for Amazon, The Cosmopolitans, his first foray into serialized work (excepting an episode of Homicide: Life on the Street, which he directed). It’s another autobiographical effort set in Stillman’s home of Paris, focused on a few American expatriates there, youths of uncertain occupation enjoying the traditional charms of that city. The pilot, which may or may not reflect his future directions, is characteristically strong:

“No, I’ve had that, not being able to work when there’s someone in the apartment. The problem is I can’t work when there’s no one there either.”

Then there was his resplendent Love and Friendship (2016), an adaptation and accentuation of Austen’s early epistolary novella, Lady Susan. This is an unusual showcase for Austen’s most venal character, the scheming Lady Susan, with substantial additional dialogue and occasional tweaks of plot supplied by Stillman. Lady Susan was an ideal canvas for improvement: an early, unpublished, and seemingly unfinished work. As Stillman once commented, “It wouldn’t be pure Jane Austen, but I could add to the Jane Austen library rather than just take down some masterpiece and turn it into an audio-visual piece.” It’s a fascinating work, feeling neither entirely like Austen nor entirely like Stillman, with portions unmistakably the work of each. Lady Susan is an unusually scheming and manipulative character in the Austen canon, and yet Stillman has been very keen to dismiss any notion of its putative modernity. As he explained in an interview exchange in the New York Times:

Interviewer: There’s almost no redemption in this story. Lady Susan never realizes the errors of her ways. She’s more like an Oscar Wilde character than a Jane Austen heroine. Do you think it’s a more satirical and slightly more contemporary than her other books?

Stillman: I don’t like to say that. That’s something that’s said a lot now, like if you want to sell people on going to see something that’s set in the past. They say, “Oh, this has a snarky, modern sensibility.” And I don’t want to say that at all, because I rather prefer the 18th century. For me, it’s not a good thing to say it’s contemporary.

If there is a trait that defines Stillman, it is his Burkean aversion to the presumed superiority of the contemporary. Though he doesn’t blindly cling to the past, he rejects the idea that orders and arrangements of yesteryear are simply outdated and should be rejected.While he often is identified as a political conservative, he has typically resisted any such simple characterization. He was reared in a home of strident liberalism, and in 1969, when a Harvard freshman, he escorted a debutante to the Junior Assemblies ball at New York’s Plaza Hotel with a Students for a Democratic Society button tucked under the lapel of his white-tie-and-tails. But since then he has rejected the obstreperous liberalism of his parents and his youth (and visible political enthusiasms of most kinds).

“Everything in our family was about dislike for Republicans,” Stillman once recalled, “people who played golf, Episcopalians, country club members, certain towns like Edgartown, these very conventional summer resorts…We had to despise all these people, make fun of them. And then in my life I actually met these people, and they were likeable and funny, and actually nicer than the political people. So I really loved taking those political glasses off, and I don’t want to get back into it on either side. I don’t want to like or dislike people based on their politics.”

He was listed as New York editor of the conservative American Spectator for some time, but his slight output there mainly paralleled a similar refusal to derogate those classes loathed by his parents and much of popular media. As he wrote in one review of a volume on television: “Businessmen, the military, small town residents, the rich, gun owners, fundamentalist Protestants—generally anyone who might vote Republican—were portrayed as ludicrous or evil. Conversely, the poor, teachers, members of ethnic minorities, people from outer space, people like TV writers, were portrayed as good.”

Whatever his political alignment, Stillman possesses a remarkably conservative artistic sensibility, and his body of work powerfully articulates the value of ideas and classes accorded almost no respect in recent cinema. As Austin Bramwell wrote in First Things:

His films are not valiant defenses of all things now discredited, but neither do they deride them with the sort of ironic detachment that has become so en vogue. Rather, Stillman’s films simply show how good can come from the most unlikely sources. Thus, disco may have been superficial and narcissistic, but it also returned conversation, dancing, and formal dress to popular music. Americans abroad may be simpletons, but they are more honest and willing to stand up for the right than their European counterparts. Debutante balls may exist only for the privileged, but they also encourage good manners and liberal education (rather than the narrow  philistinism found among the upper crust in popular movies such as Titanic). Lastly and most importantly, American Protestantism may not be rich in mystery or philosophic insight, but it is a religion of simple truths and simple faith.

An element of Stillman’s work can be traced to his stylistic and literary influences, earlier modes of cinema and literature less convinced of the good or evil of certain classes or ideas. Farran Smith Nehme notes his obvious influence by earlier filmmakers Ernst Lubitsch, Preston Sturges, and Gregory  La Cava, who “poked fun at the rich without rancor.” Fred Astaire’s musical comedies of the 1930s and 1940s are another declared love, no surprise in a cinema dappled with dance numbers. He’s often been called a WASP Woody Allen and has acknowledged the connection. His literary influences are diffuse and clear: Evelyn Waugh, J.D. Salinger, Samuel Johnson, Balzac, and Alexander Pope. And also far more demotic figures, such as Donald Duck, Lady and the Tramp, and Bambi are likely to make appearances.

His stock in trade is characterization and dialogue, and here he excels beyond most of his contemporaries. It’s impossible to argue that Stillman’s dialogue isn’t his greatest asset, whether quips or monologues. A few examples:

I haven’t been giving you the silent treatment, I just haven’t been talking to you.

The common image of divorce and decadent behavior being prevalent in New York social types is not really accurate—that’s more Southhampton.

Anything I did that was wrong I apologize for; anything I did that was not wrong I do not apologize for.

You know that Shakespearean admonition, ‘To thine own self be true’? It’s premised on the idea that ‘thine own self’ is something pretty good, being true to which is commendable. But what if ‘thine own self’ is not so good? What if it’s pretty bad? Would it be better, in that case, not to be true to thine own self?… See, that’s my situation.

Given Stillman’s sprightly dialogue, it is easy to miss his distinctively effective style of filming conversation, going beyond line deliveries to capture also their impact. “I just think people looking at each other and how they react is the cool thing.” He credits much of the kinetic drive of filmed conversation to regular director of photography John Thomas. The noted director Stanley Kubrick, after watching this technique in Barcelona, commented, “This is a new kind of cinema…dialogue advancing story in an interesting way.” He then hired Thomas as his photography director for Eyes Wide Shut.

For a director whose work is often arch, filled with characters from the elevated classes who occasionally seem ridiculous, Stillman disavows both snobbery and camp readings of his work. His peers frequently comment on his essential sincerity as a hallmark trait. As Haden Guest writes in an essay on Barcelona: “Stillman turns to comedy not as a debased, tired, or parodic form in need of reinvention but as a means of sincere reconciliation and renewal.’’ Guest adds that Stillman “embraces romantic comedy as a philosophically grounded genre driven toward a Shakespearean restoration of order and community.”

We might find another final guide in the essay of Lionel Trilling on Mansfield Park, a novel praised by Tom in Metropolitan. Trilling suggests that Austen was pursuing a higher imperative than stylistic virtuosity in the novel and says that, “for the sake of its moral life, it must violate its own beauty by incorporating some of the irreducible prosy actuality of the world.” Trilling offers a pithy observation about the novel’s character that is applicable also to Stillman’s work. “It is an irony directed at irony itself,” wrote Trilling. Persons are flawed and complicated, and yet typically are what they seem to be or are discovered to be. Comedy is not, in Stillman’s catalogue, a series of skewerings, but the story of the human condition.

Anthony Paletta is a freelance writer in Brooklyn who has contributed to the Wall Street Journal, The Weekly Standard, the Guardian, and numerous other publications.