By now, Whit Stillman has achieved a unique cultural status, at once iconic and elusive. His films have such a specific, literate sensibility that devotees hoard favorite lines like beloved family recipes (‘I don’t think Ted is a fascist of the marrying kind,’ remains very dear). And though he’s oft-quoted, Stillman has been a stranger for too long–he’s been executing his own Maneuver X, Barcelona partisans might say. After a dozen years, he’s back. Damsels in Distress, his university picture starring Greta Gerwig, opens in New York and LA today.

We spoke this week in a Madison Avenue hotel suite where Bloomberg News, of all things, was on the television in the background.

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David Coggins: Is that Alexander Olch in the first shot of Damsels in Distress?

Whit Stillman: It is, and he also repeats, at the end, when they talk about cool people. His very recognizable silhouette goes through twice, kind of bad continuity. He’s wearing a suit and sneakers. I think you should talk to him about shoes.

DC: I will. It’s funny you mention coolness though, because in all your films there’s a distinction between people who understand what’s going on and those who are struggling to figure it out, and a lot of analysis about that fine line.

WS: I agree with the Violet character [in Damsels in Distress] in that debate, that if you really want to be cool, you have to tamp down your humanity a little bit. You’ve got to de-emote, depersonalize. But I tried to be fair to Lily’s character, and what she says does make sense, that yes, we need normal people so things work right.

For instance, I find dealing with Sony Pictures, I’m not so good with the deadlines, because I want it to be really right, but they need to get it by a certain time, so there’s a bit of a drama when ‘Whit needs to approve something.’ It’s been good, but I feel that the practical people get things done. And often I find there’s a conflict between a certain kind of particularism, and getting-it-done-ism. I don’t like to say perfectionism, because nothing is perfect, but if you want to get things in a particular way, that goes against getting it done on time.

DC: And does that happen mostly in the writing process?

WS: Well it definitely happens in the writing process, and that’s part of my disgrace, because it’s been so many years without making a film, partly because the projects just didn’t get off the ground for one reason or another, but also, the lengthy writing process hasn’t helped that. Then, for instance, when I showed the film in Venice and Toronto, I felt we’d just closed it up quickly, to get to make a fast date, and that we really hadn’t finished the sound edit, and the music mix. So the sound editor was not available until something like February, and so suddenly we’re kind of finishing the film very close to the release date, which was…fun.

DC: But when you talk about the writing process, how much do you plan ahead of time and how much changes as you go along?

WS: One of the things I really hate, and try to avoid, is when people ask me to do an outline, or a treatment of what the project is. I find it a fatal idea. Because what they’re going to get is absolute cliché, obvious, stale, dead stuff. Then, even though you see through the dead stuff, it’s like an albatross around your neck. Even if you can escape, which, rarely can you escape it yourself as the creative party, they have it in their head that it’s supposed to be that way, and generally those ideas are really uninteresting. I found a big problem with my Jamaican film that BBC films wanted me to do a treatment first, and I felt it was a total albatross.

DC: You’ve got very recognizable characters,

very strong-willed, they’re trying to improve themselves in some way. Why do you gravitate towards people like that? Whether it’s Ted in Barcelona mastering marketing skills, or characters in this film trying to help other people to help themselves. That seems to be a recurring theme for you.

WS: Well it’s a thing that interests me, and I sort of know whereof I speak with that. Another thing is big characters, big personalities–sometimes those are funny personalities. So the Kate Beckinsale and the Chris Eigeman characters in Disco, and the Violet character is a refinement and an extrapolation of those characters. In fact Greta said, when she was playing the part, she didn’t want to have Kate Beckinsale and Chris Eigemans’ rhythms in her head. She wanted to make it her own.

DC: That’s interesting. You’ve worked with certain actors repeatedly, and have a very specific way of delivering your lines. What’s it like when you deal with a new actor who tries to deal with your precise style of dialog?

WS: Well both Chloë and Greta have a similar quality of existing brilliantly and naturally on the screen, in a very interesting, intelligent way. I would say, Chloë’s more instinctive, and Greta’s more conscious. It’s not that one is better, they’re just two different ways to do it.

DC: Do they resist it? Do you have to help?

WS: No, not at all. There’s a modulation of what we’re doing. I didn’t want Greta to feel that she had to make Violet a funny character. It had to be a sincere character, who in what she does, becomes humorous. But she’s totally sincere about it, she doesn’t have to be funny. So that was just a little thing of trying out ideas in the first few days. I would say the most challenging thing though was that Adam Brody had to play a Chris Eigeman character without being Chris Eigeman, and I think he really pulled that off well. Because Adam brings to it this very likeable personality, and then he does the Chris Eigeman thing pretty well as his own thing.

DC: He does very well. Though Chris Eigeman sets the standard.

WS: My dream project, an idea that I’ve actually worked on, could use all four of them. It’s almost as if they could be different generations. Chloë is not very old at all, but Chloë and Greta, and Adam and Chris, I think to have them all in the same film would be interesting.

DC: Your films seem to take place in the recent past, though there is a cell phone in this one.

WS: I’m glad you noticed that. You’re one of the few who did, a lot of people say ‘There are no cell phones in this film,’ and I say ‘Well there is, actually.’ There was supposed to be a laptop, the scene where he’s writing his ‘decline of decadence’ paper with Lily, though we took it out.

DC: Does setting a film in the past give you more freedom?

WS: The first three films, were mildly idealized versions of actual times and places. Reimagined, but very close to things I observed, using all those things one notices and remembers to try to make them interesting and textured. This film is an imagined world, it’s an unreal fantasy world, that also has something to do with university reality, it also has something to do with college films. So it has something to do with Animal House, it has something to do with Rushmore. The director of the Dublin Film Festival, she said it was ‘Jane Austen meets Animal House.’

This film’s more stylized, and either heightened or lowered reality, and there’s more freedom in this film. One of the ideas was, for the first time, I’m not trying to say that this is not contemporary. So, we’re shooting it now, there are these things, we’re going to make no effort to have anything but now, really. We’re not trying to emphasize now, but there it is. But, the utopia that these girls are trying to put on Seven Oaks, so they, like me, love a lot of things about the ‘50s and the early ‘60s, like the good things. So instead of going back and making Mad Men that period a drag–cause I find all those things that are period, I don’t really know that show but generally movie and TV versions of period, I find almost too much art direction. It’s like, everything in 1962 is 1962, when in fact, when we’re in 1962, almost everything around us was made earlier. Also, in your head, you don’t really think, ‘Oh I’m in 2012, everything I do is portrayed in 2012,’ you’re just existing. So there’s this fakeness about period. In this case, they just love this idea of the world of Grace Kelly, the world of Audrey Hepburn, the world of good French perfumes and fashions, from that period. It’s before the catastrophe. For me, I found the late ‘60s as just a catastrophe, and this is a kind of dream world of before that.

DC: The characters are reflexively preppy, they’re not make an ironic statement about wearing a pink Oxford shirt. Can you talk about the idea of preppy, you’re wearing pale green socks at the moment.

WS: The socks were a gift.

DC: You rarely hear that line about socks. But there’s style in your pictures, and a lot of men in tuxedos.

WS: In a way, the little grain of sand that made Metropolitan, was this comment that Vincent Canby made about some Fred Astaire film series, that ‘People don’t wear clothes like this anymore.’ I was, my frustrated, strange, post-college thing, post-college spirit of unemployment, and I wrote a letter to the Times, that ‘Yes of course people still dress that way these days,’ and I think I signed it the Executive Director of the New York Committee to Save the White Tie. I formed an organization with my friend Kimball Chen and I wrote this letter because you know that period of frustration when you’re doing nothing, you write letters to the paper. Now you’d be an Internet commenter. So it stuck in my craw and then I was thinking that would be a good way to do a low-budget film. If they were all dressed to the nines, it would look more significant. So I love that relationship with Vincent Canby, because he was a really great critic to us, really put us on the map.

DC: And the characters are still very aware of their appearance, one character rents his tuxedo, and everybody notices that his coat is not a winter coat–there’s a high awareness of clothes, would you say?

WS: I guess that’s true. Growing up, I had a very strange experience, where I was in an unhappy environment in Washington, where everybody was very political. Our family was sort of prosperous then, my parents were still together. And if people came over, you hid your toys, because they would criticize you for having too many toys, or for being too rich or something like that. And then I went to this blandly materialistic, very normal school called Millbrook.

The flair factor at Millbrook school, is that it had a school zoo, and the cool thing to do at the school was to be a zoo head. So you had these woodsy, nature types who were the cool guys at the school, and what they do is take care of little animals. That was the cool thing to do, to take care of little animals. It was a really great atmosphere at Millbrook, really nice people, real eccentrics. The school loved eccentricity. If someone was really eccentric they became the most popular person in class, because they were so crazy. And there was a huge dance culture, it was ‘dance Bob, dance,’ because you’d go to a mixer with the girls’ school, and if you could be a cool dancer, a ladies man, conqueror, and break hearts, or at least win hearts, and dance well and be cool. I remember a guy coming into my class when I first got there, and getting my clothes, and my poor mother had bought most of my clothes at the local Giant supermarket, and it was humiliating, the clothes I had, but somehow the spirit, the attention paid to you, was so funny and so nice, it was completely disarming. It was this frank materialism, and these people were total characters. This one place in Washington, they supposedly had good, anti-materialistic values, versus this place where they had just no pretension to good values at all. Except they’re nice to eccentrics, and animals, and people who bought their clothes at Giant. So Millbrook was exhilarating and liberating. I had a wonderful uncle, and he used to tell stories about how Mrs. Rummell, the style maven of the ‘30s, brilliant architect, who designed Avon Old Farms’ really beautiful campus, and she had a rule that everyone would wear a gray flannel suit from Brooks Brothers. He said it was so liberating, you just get your two grey flannel suits and we all dressed in these nice suits, but that’s all there was, so there’s no competing dress or anything like that.

DC: I like it. You mention dancing at school, and dancing has been in all your films, it’s very much a part of it. It’s like it’s the antidote to hyper-articulate people, it’s purely physical, about action.

WS: Right. That song, the main song they dance to in Damsels, it’s a Gershwin song, and it’s really an Ira and George Gershwin song, because the lyrics to that song are wonderful, because at one point we thought we might have to create our own Gershwin song if we couldn’t license it, and I just adored the words to “Things Are Looking Up.” It’s a beautiful depression antidote, and antidepressant, because it embraces the melancholy. You know, if you look around trying to cheer you up, that’s terrible. You have to acknowledge the melancholy, before you bounce off it.

DC: The song may be sad, but you clearly like dancing.

WS: I adore it, I absolutely adore it–it was Millbrook that did the dancing for me. And the smear about white people and preppies not dancing, is complete garbage.

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David Coggins writes for Bergdorf Goodman. In a moment of weakness, he recently joined Twitter.