The American indie director Whit Stillman has made only five movies, but if you’re an aspiring cineaste, you need to see them all.

Focusing exclusively on young members of the upper crust, Mr. Stillman humanizes a class of people typically derided for belonging to the privileged one percent. Mr. Stillman endears audiences to his heroes by depicting them as prosaic mourners, the last of the noblesse yearning for a forgotten age of civility.

Like the British author P.G. Wodehouse, Mr. Stillman possesses the delicate ability to present serious topics through lighthearted and often absurd-sounding dialogue. He injects the aristocracy with a whimsy underscored by an urgent desire for order and meaning in an often inexplicable world. His best films fit the author Joan Didion’s assessment of the nature of American art. “Every real American story begins in innocence and never stops mourning the loss of it,” she once wrote for National Review. “The banishment from Eden is our one great tale, lovingly told and retold, adapted, disguised and told again.”

So it goes for America; so it goes for Whit Stillman. Here’s an admittedly subjective ranking of all his films. No matter the order, see them repeatedly—if you can.

5. Damsels in Distress (2011)

Everyone’s talking about Greta Gerwig’s Lady Bird right now, but did you know her first coming-of-age story was with Mr. Stillman? Damsels is a college story, starring Gerwig as an idealistic preppy attempting to start a dance craze at her elite East Coast school. Mr. Stillman creates a wacky college environment—too pure to resemble any existing school—that treats millennial tendencies toward depression and feelings of inadequacy with an appeal to innocence. It’s definitely Mr. Stillman’s weakest film, but Damsels offers a complex alternative to the likes of college frat-house classics like Animal House.

4. Love and Friendship (2016)

Mr. Stillman’s movies are often compared to Jane Austen novels, but it was not until Love and Friendship that he directly adapted one. The movie is a wry take on Austen’s posthumously published epistolary novel, Lady Susan, and it’s a biting costume drama. Kate Beckinsale stars as Lady Susan Vernon, a conniving disenfranchised aristocrat, seeking to secure profitable marriages for both her and her daughter. A great admirer of Austen, Mr. Stillman understands that although the nineteenth-century author’s work is often perceived as stuffy, it is this very stuffiness that makes it so funny. And that’s just what Love and Friendship is.

This movie is as elegiac in its subject matter as it is in its title. It centers on a group of New York City yuppies in the very early 1980s who use disco clubs to meet members of the other sex and form meaningful relationships. The Last Days of Disco mourns the loss of structure and meaning in high society—namely, the institution of debutante balls. The movie is a shadier version of Mr. Stillman’s first film, Metropolitan. Because no social structure exists to help these young privileged people forward in life, they are forced to baptize disco into something nobler than it really ever was. When the craze dies, they can do nothing but try to find meaning in the whole experience.

2. Metropolitan (1990)

Mr. Stillman’s best-known movie, Metropolitan focuses on the dying debutante culture of the late 1970s Upper East Side. Through the perspective of Tom Townsend (Edward Clements), a self-avowed Fouriest, the audience meets the scions of the rich—only to find they’re actually pretty nice people. The movie inverts the popular trope of the outsider-who-dismantles-the-elite. By actually relating to his wealthy peers, Townsend discovers their humanity and, in the end, becomes close friends with all of them. Metropolitan was nominated for an an Academy Award for Best Screenplay, and rightly so. Watching it is like reading a psychological novel.

1. Barcelona (1994)

Mr. Stillman’s most ambitious film, Barcelona, follows the relationship of Fred (Chris Eigeman) and Ted Boynton (Taylor Nichols), two Chicago-born cousins who cross paths in Barcelona, Spain. The movie is a fish-out-of-water tale, making light of how peoples of different nationalities often have trouble understanding each other. But, like MetropolitanBarcelona is so compelling because it subverts an established stereotype about Americans. Rather than making these expats ugly or mean people, Mr. Stillman endows Fred and Ted with a great capacity to love. The movie ends like a Shakespearean comedy: Everyone gets married and all tension is resolved. Barcelona is the rare instance of fulfillment in the Mr. Stillman oeuvre. Only by finding love and settling into marriage can his characters ever truly find happiness.

Republished with gracious permission from the Intercollegiate Review (Spring 2018). 

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