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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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4 replies to this post
  1. I have seen all Stillman’s movies, and he is truly unique in movie-making today. I believe that Metropolitan is his best far and away, although Lady Susan is a close second. The thing he does so brilliantly is to find actors who can toss off the really smart dialogue with a kind of blase sweetness. Even the unlikable characters do this, so that in the end you like almost everybody, even the villains.

    What is unfortunate is how cheap that style can become if you don’t have appropriate moral seriousness behind it, which I felt was the case with Damsels in Distress, which is too bad, since there was so much that worked in it.

    • Maybe the podcast on Damsels in Distress that Flagg Taylor, Titus Techera, and I did over at American Cinema Foundation could change your mind about the moral seriousness of the film. We also have a podcast on Last Days of Disco. See the link in the “website” slot.

      Funny that you revert into calling Love & Friendship by the name of the novella, Lady Susan, that it adapts! Blase sweet regards from another Stillman fan, CES

  2. The one maddening thing is that Stillman has made just five films (plus The Cosmopolitans for Amazon which I have yet to see) in nearly thirty years. He is now 66 – but in these days of working film makers nearing the age of 90 such as Agnes Varda and Clint Eastwood he potentially has plenty of time to complete several more movies. I remain intrigued by his Jamaican-set Dancing Mood project.

    Two quibbles about this fine review of Stillman’s films: Metropolitan was merely nominated, not a winner, for an Oscar and I would place the delightful nutty Damsels in 3rd place. I think I’m the only Stillman enthusiast who loves it!

  3. I actually agree with your ranking – I might switch up “Metropolitan” and “Barcelona”, but I can make an argument for both being 1 or 2. “Metropolitan” was a loose take on Jane Austen’s “Mansfield Park”, which gives it an edge with me, since I’m a major Austenphile. I was actually disappointed with “Love and Friendship” (though the costumes were divine) – there have been about 5-6 novel adaptations of “Lady Susan” including Stillman’s, and a couple of them were a lot more “Austenesque” than what he went for in the movie, and might have made for better adaptations.

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