Whit Stillman Ditches the Middle Class and Goes Back to School

To a certain group of twenty-something urbanites like me, Whit Stillman is something of a god. I was too young to really appreciate the writer-director’s most famous film, The Last Days of Disco, Stillman’s 1998 portrait of a group of post-collegiate New Yorkers pairing up in the fading days of the disco scene. But seeing it as a post-collegiate New Yorker, the alienation resonates. I dug into Stillman’s earlier work—1990’s Metropolitan and 1994’s Barcelona—which complete his “doomed bourgeois in love” trilogy, and eagerly awaited the next Stillman masterpiece. It took a while, but after 14 years, Stillman has finally delivered. His newest film, Damsels in Distress, is another comedy of mannerlessness set at a fictional northeastern college, and hits theaters April 6. The new film is full of familiar Stillmanesque characters, still immensely relatable: imperfect, sometimes obnoxious, and all struggling to find where they fit in. Though Stillman was at the forefront of the ’90s independent film boom, he never really fit in. Despite delivering three critically acclaimed films (he received an Oscar nomination for Metropolitan), his movies lacked the gritty edge of Pulp Fiction or Boogie Nights. Rather than embrace the supercharged techniques of Quentin Tarantino and Paul Thomas Anderson, Stillman took a more classic approach to filmmaking: completing character-driven scripts, avoiding salacious subject matter, and examining the morals at play within societal constructs. “I really think films started going bad around 1942,” he tells me. Coming from him, this is not particularly shocking.

I am very nervous to meet the peripatetic Stillman for coffee at Pécan Café, a restaurant on the corner of Franklin and Varick Streets just a few doors down from the Tribeca apartment he is subletting. I had spent the week re-watching his films and feared that the writer-director would be the doppelgänger of one of his over-intellectual Upper East Side misanthropes. When speaking to members of the Damsels cast, I realized I was not alone in my apprehension. “He’s a man of such etiquette,” Adam Brody, who plays the film’s love interest, told me. “I’ve since given it up, but when he used to email me, I would be very self-conscious about my replies, making them very formal in order to match him.” Greta Gerwig admitted that, to prepare for her lead role, she “tried to live in a way Whit would approve of.” But as soon as Stillman and I sit down, my anxiety abates. Dressed in a white dress shirt and a colorful plaid blazer, Stillman resembles a college professor rather than an Academy Award nominee. He’s soft-spoken, inquisitive, and lovably curmudgeonly, and he apologizes for bringing along a plastic shopping bag carrying a crumpled dress shirt that he plans to drop off at the cleaners after our interview. Almost immediately, he reveals how he has started to catch on to the anticipation of his first film in nearly 15 years. “[Damsels] was selected as the surprise film at the London Film Festival,” he tells me, “and it was a really bad idea. Everyone was expecting My Week With Marilyn or the new Twilight film. That was their taste. The good thing was that the press was there and they really liked it, but the response on Twitter was incredibly negative—people seem obsessed with how much they hated it. they really took it personally.” (I should note that in 1998, the average moviegoer did not have an accessible public outlet on which to play movie critic.)

Though it’s surprising to me that anyone could dislike a Whit Stillman film, I recognize his oeuvre is still very much a niche market. Focusing on characters living in the upper-crust of society, Stillman’s films likely alienate the movie-going masses. But despite its sociological exclusivity, his work still points to larger truths about man’s place within society. He also succeeds at creating a surreal universe of his own. Damsels is the first of Stillman’s films to take place in the present day, yet his stilted language and vintage-inspired costumes, not to mention the Gershwin song-and-dance number at the end, create a severe dissonance for modern audiences. Stillman’s own tastes tend toward the classic comedies of Golden Era directors like Preston Sturges. (He even proudly compares Gerwig to Irene Dunn. “Have you seen The Awful Truth?” he asks. “You need to watch it.”) While incorporating some uncomfortably comedic situations, like when one damsel is coerced by her boyfriend to have anal sex based on a fringe Catholic philosophy, the film still inhabits the Whit Stillman universe wherein young women find comfort through dance and where their dashing suitors force them into “tailspins,” the antiquated term Gerwig’s character prefers for a depressive state. 

Audiences tend to identify with the outsider. Huck Finn was a hero, as was the titular Shane. But Stillman’s protagonists, outsiders all, are never completely heroic. Metropolitan’s Tom Townsend, whose lower-class status at first garners the audience’s sympathies, soon reveals himself to be a snobbish heartbreaker who tosses away the affections of the innocent Audrey Roget. In The Last Days of Disco, ’90s indie queen Chloe Sevigny plays Alice Kinnon, a timid and cold editorial assistant who, despite being tragically unlucky in love, also takes out her aggression by kicking a puppy while jogging in Central Park.

The same messiness comes into play in Damsels. At first glance, Lily, a new transfer student at the less-than-competitive Seven Oaks College, seems like the rational counterpart to the fibbing, obsessive-compulsive Violet, the leader of a trio of girls who favor tap dancing and perfumes as suicide-prevention tactics. Things get complicated once Lily and Violet fall for Charlie (Adam Brody), a super-senior who tries to pass himself off as a young professional working in the field of “strategic development.” The young women find this incredibly enticing despite not knowing what such a position entails. Through the course of the film, Lily realizes that Violet’s affinity for sad-sacks and losers, as well as her aspiration to change the course of humanity by starting a new dance craze, bespeaks a shallow nature. But Violet also shows a curious self-awareness. “You probably think we’re frivolous, empty-headed, perfume-obsessed college coeds,” she tells Lily early in the film. “You’re probably right. I often feel empty-headed. But we’re also trying to make the world a better place.” “My character sort of plays along with the audience’s reaction [against Violet],” Tipton told me. Gerwig originally auditioned for the Lily role, but was more interested in Violet. “She’s totally crazy and totally a liar, yet totally sincere,” Gerwig said. “She is all of those things, and she’s so critical. But she’s also critical of herself and, in a roundabout way, trying to make the world better.”

Despite her flaws, Stillman makes it clear that it’s Violet who is the film’s hero. “The Lily character is actually the nemesis of the film,” he explains. “People need all the help they can get not to dismiss Violet as the mean girl.” It’s not necessarily the film’s fault that most audiences might miss the mark; on the contrary, it might be evidence of Stillman’s powerful writing. He’s able to craft characters who aren’t cut-and-dry, whose moral ambiguities are as important as, if not more important than, the film’s plot. “The secret key to the films,” he continues, “is that the outsider characters are not portrayed very sympathetically. There’s this fiction that I think is very dangerous in almost all popular films that have the sympathetic, identifiable outsider character who’s a good person while the other people are bad. In my films, it’s the outsider character that doesn’t learn anything. A lot of people reject that.”

Stillman’s obsession with outsiders and insiders might stem from his past. The son of a Democratic politician and the grandson of E. Digby Baltzell, whose sociological study of the American protestant class system popularized the term “WASP,” Stillman navigated the demimonde with charm, invention, and the moral ambiguity one finds in his heroes. “The only way I survived debutante parties and awkward social situations was by making stuff up about myself. I couldn’t go as myself to these things,” he explains. “You say who you are and everyone turns their backs. But if you just make something up, generally they are much more interested. When I went to those parties, I found that if you were from Tyler, Texas, or Tyler, Idaho, those very pretty, preppy girls were really interested. But if you were just Joe Preppy from Madison Avenue…”

That goes a long way explaining why the 60-year-old Stillman still examines the social lives of those in their early twenties. “That is the identity formation period, when you’re making important romantic and career decisions,” he explains. “Friends ask me, ‘Why don’t you do stuff about people our age?’ Basically, you’re 16 all your life; once you become 16, nothing changes except that you grow feeble and die. The plight of the 50-year-old? Meh.”

It was a group of young actors and filmmakers who inspired the completion of Damsels. Upon meeting Gerwig, Stillman was fascinated with the ways she and her mumblecore cohort financed their films on miniscule budgets. “I’m not sure about the actual films themselves,” he says, “but the whole style of mumblecore is an exciting thing that revitalized this film.” The micro-budget financing of films like Hannah Takes the Stairs and The Puffy Chair pushed Stillman to make Damsels on the cheap. Despite his critical success with his earlier films, he found it difficult to maneuver the business side of the film industry. “There was a bubble,” he says of the independent film movement of the late ’90s. “It didn’t pop exactly, but the air was going out quickly.” “Indie” quickly became a buzzword and its own commercialized genre. “After Disco, people told me, ‘No, Whit, you’ve got to do things the industry way now,’” he confesses. “The industry way for me was not making a film for ten years. You do this star-casting and equity financing, and you wait around forever. It’s just wheels spinning.”

Gerwig confesses that Stillman’s name was on a list of directors she handed to her agent. When she heard he was casting Damsels, she said, “I was just thrilled that he was making a movie because I wanted to watch it.” Analeigh Tipton, whose role in Damsels is her largest to date, admitted that she wasn’t familiar with Stillman when she was offered the chance to audition. “I was shooting Crazy, Stupid, Love and sitting in the trailer with Julianne Moore, and she asked me what I was working on next,” Tipton told me. “I said, ‘I don’t know. I’m looking at this Whit…Somebody project?’ Julianne threw her makeup down and said, ‘Whit Stillman?!’ I thought, ‘I guess I can’t say no after that.’”

It must be an ego boost for an A-list actor to eagerly shout your name, but Stillman hardly reacts when I retell Tipton’s story. After all, should Stillman make another movie in the next decade (he is working on a script set in 1960s Jamaica), it’s unlikely he’ll cast boldfaced names in place of younger, inexperienced actors. But he’s got some other ideas, too. “Musicals have been wrecked by Broadway audiences,” he declares. “I was thinking of doing a period musical, but the audience would have to be in period, as well. They wouldn’t be allowed to give standing ovations or squeal and yell at the stage.”

And with that, Stillman grabs his dirty laundry, scoots back his chair, and heads outside.

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