When I was 16, I lived on the outskirts of San Francisco. I skated at the Embarcadero Plaza (“EMB”). I was particularly partial to the Bay Area rappers RBL Posse, Dre Dog, and B-Legit. I was failing several classes at a large public high school. Like many Northern Californian teenagers I used the word “hella” with astonishing frequency.

This is to say that when—on some kind of long-forgotten whim—I rented Whit Stillman’s first film, Metropolitan, I was leading an existence far removed from the cloistered world of Upper East Side debutantes that Metropolitan so artfully depicted. And yet something about that film suggested the vague outlines of some kind of higher life. The film made me want to author the kinds of sentences—express the kinds of sentiments—that were the film’s true stars.

For this interview, Mr. Stillman gamely agreed to discuss his latest film, Damsels in Distress, and also answer questions about skateboarding. At the very least, an author conjectured that talking about skateboarding would be a way of circumventing some well-trod Whit Stillman territory. (Reporters often ask him about the term “preppy” or use the terms “Brahmin,” “WASP,” or “patrician” to describe him.)

It is, however, tempting to say something that has already been said ad nauseam. Whit Stillman does seem like a character in a Whit Stillman film. When, for instance, a reporter asked him about skateboarding, he became hella wistful.

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Joel Rice: Congratulations again on the release of the film. We have a couple of very tenuous connections. I went to Kenyon College. Chris Eigeman, who starred in your first three films—Metropolitan, Barcelona, and Last Days of Disco—also went there.

Whit Stillman: Oh, cool. A lot of my friends went to Kenyon.

JR: Also, when I was 16, one scene that really spoke to me in the film Metropolitan is when the character Nick, played by Chris Eigeman, is trying to persuade the character Tom to start attending debutante parties but Tom is resisting. Nick says, “What principle is this? That one should be at home, thinking about the less fortunate?”

WS: Good. [Laughs.]

JR: And just a word of warning. I write about skateboarding. I have some conventional questions. But toward the end I have some questions about skateboarding. You can just interpret them any way you wish. I am not trying to make you look silly or stupid.

WS: Okay. Good.

JR: How do you feel about interviews generally? Do you find them fun or a nuisance?

WS: I like them. It’s a culmination of a process. I mean, we have finally completed something we can talk about.

JR: What would you like to say about your new film, Damsels in Distress?

WS: It’s a very serious film.

JR: Am I to take that literally?

WS: Yes.

JR: Would you like to expand upon your comment that Damsels in Distress is ‘a serious film’?

WS: No. I’d like just to keep it enigmatic, if you don’t mind?

JR: Sure. That’s fine. Are you pleased with the film? When you see the finished product, how does it feel?

WS: Yes. I am very happy with the film. But when I look at the film, I look at other people’s work. So I look at the actor’s work. I look at the composer’s work. I particularly love the music that the composers Mark Suozzo and Adam Schlesinger came up with, and I am really happy that Milan records has put it out as a soundtrack CD.

JR: Great. Okay, so this is my longest question. And again, a word of warning, it has to do with skateboarding. So just so you know where I am coming from, I grew up in San Francisco at a time when the city was the acknowledged center of the skateboarding world…

WS: Is it the hills that made San Francisco a big capital? Is it like Hawaii and surf? The hills?

JR: Very true. The hills make it attractive to skateboarders. Also, at the time there was a plaza called the Embarcadero where skateboarding as we know it was being reinvented. Anyway, while I loved skateboarding more than life itself, the scene had a kind of unsavory, thuggish edge to it. Then I saw Metropolitan, and I thought, “Wow, this really seems like a really different world. I want to know more about this.” There was something about the world you depicted that was tremendously appealing.

WS: Oh, cool. Thanks for saying that. That’s great. Thank you very much.

JR: But in a way, when I saw Metropolitan, I was coming from a really different place than the place depicted in your film. What about your films do you think connects with people outside the demographic you’re sometimes associated with?*

WS: I think there must be types of people… people with a sense of humor are those who like the films, I would say. [Laughs.] Judging from some of the reviews. But it’s good to see the positive reaction that the film got at the Bombay Film Festival, also known as the Mumbai Film Festival.

JR: Any particular reason that it resonated with Indian audiences?

WS: I don’t know. There’s a lot of formality in different societies. I do remember meeting an Indian man in the Hemingway Bar at the Ritz hotel in Paris. And he was Oxford- and Cambridge-educated. What do you call it? Oxbridge-educated. And he wanted to insult us, so he called us “villagers.” Apparently that’s an insult in India. “Villagers.” We really enjoyed meeting him.

JR: But you feel like your films reach well beyond the milieu they depict?

WS: Yeah, I think that people in the milieu depicted, if there is a milieu… I think this film Damsels in Distress has a much broader milieu than some people think. It’s in a more general collegiate, or university, milieu, although it’s very fanciful.

You know, there are kindred spirits who have nothing to do with milieu, if you know what I mean. Like, if there are people who like a certain kind of comedy rather than being very drama oriented.

I mean, I am the original skateboarding generation, because skateboarding was created when I was a boy. I remember jumping on one of the first skateboards. We were very boring about it. For us skateboards were just good transportation. [Laughs.] We would just roll down hill on them.

JR: But it was a very exhilarating feeling, I imagine.

WS: Oh, I loved it. It was almost as much fun as throwing snowballs at the cars coming down our street. But only soft snowballs, never icy ones.

JR: You anticipated one of my other questions, which was, “Have you ever tried skateboarding?” So the answer is yes.

WS: Yeah. I must have been present at the creation. The first months that skateboards were around I had one.

JR: Was your family supportive of it?

WS: Oh, yeah. But it was a really innocuous thing then. It was after you did your homework you go out… We were living in Georgetown, Washington, then. Behind the townhouse we lived in, there was an alley leading to the garages in the back. And it was at an incline, so I could go from the garages in the back and slide down to the alley in the back and turn down the hill. The sidewalks were brick. So you got a bit of a bump as you went down.

JR: Does anyone in your family enjoy skateboarding, or do you tend to like more traditional sports, such as tennis or squash? I don’t mean to stereotype you in any way. Do you play sports? Did you grow up loving sports?

WS: I only like sports in which horses are the protagonists.

JR: Nice. In my utopia everyone would be skateboarders, but we would all talk with the depth and philosophical sincerity of your characters. I know you lived in Paris. Were you ever struck by the sheer beauty of skateboarding?

WS: I found it kind of sympathetic. In my neighborhood in Paris, the kids were skateboarding. It seemed like a good thing. I mean, it’s kind of a cool way to stay limber and in shape.

I like ska music. I believe at one time ska music was the preferred music of skateboarders.

JR: This is my last skateboarding question. I promise. My sense is that every year youth culture gets more and more extreme. Your characters often blanch at the coarseness of contemporary life and…

WS: No, I don’t think that’s true.

JR: You don’t think that’s true. Okay. Please go ahead.

WS: I think everything has multiple directions. So actually things are less extreme now than when I was in university. The university was much more extreme when I got there in 1969, when I first got there, than it is now. It was very extreme in September 1969, I can tell you. On college campuses now, there is more ’50s stuff going on than 1969 stuff.

JR: Okay. This is still vaguely related to that idea of coarsening… In skateboarding there’s this kind of stereotypical narrative: Information technology and the ease of filming and easily being able to put film on the Internet has effected skateboarding culture, in that many kids are really more into watching themselves and marketing themselves at a young age rather than enjoying skateboarding with the intrinsic innocent pleasure that you describe. Could you comment on that general trend? I know you left cellphones and a lot of technology out of Damsels in Distress.

WS: Yeah. There is a cellphone present in the film. Adam Brody’s character uses a cellphone in one scene, and we had laptops and stuff like that in earlier scenes that we trimmed. But I do kind of worry that so much of our time is going toward reporting on things without actually being protagonists. I think protagonism is more interesting than commenting and observing. And I think we should sort of tune stuff out so we can concentrate on our lives as protagonists.

I can just waste tons of time on the Internet. And I don’t want to do that. And some things I have tried not to pay attention to, like reality television. You don’t want to pay attention to that. Not to necessarily dis something else. Though that’s part of it. We should try to focus on productive, creative activity and not be distracted by all this stuff that’s going on. To focus on whatever creative activity is, or whatever our protagonism is, our main work.

JR: All the sorts of white noise…

WS: The cultural noise.

JR: Thank you so much, sir. I really appreciate it.

WS: You too, Joel. Have a very good Easter.