If you were in the market for witty, literate films about sophisticated young people during the 1990s, the name Whit Stillman tended to prick up your ears. Stillman, born John Whitney Stillman, came out of nowhere with his first feature, 1990’s Metropolitan, which centered on a group of privileged young New Yorkers during debutante ball season. The film, made for a pittance, earned an Oscar nomination for Best Original Screenplay, won Best Picture at the Independent Spirit Awards, and made Stillman a darling of the burgeoning indie film scene. He followed up Metropolitan with two more films in an unofficial trilogy. 1994’s Barcelona was inspired by Stillman’s experience living in Spain in the 1980s, while 1998’s The Last Days of Disco followed two young women (Chloë Sevigny and Kate Beckinsale) negotiating work, love, and the Manhattan nightclub scene.

Stillman’s film received widespread critical praise, with Roger Ebert comparing him to F. Scott Fitzgerald and others reminded of Jane Austen’s comedies of manners. But box office returns were less glowing, and 13 years went by before Stillman’s next feature, Damsels in Distress, was released. Set at a small East Coast college, it benefitted from an endearing performance by the then-rising star Greta Gerwig as one of a group of female students trying to, as Stillman put it, “keep things civil in an uncivil world.” His most recent effort was, fittingly, a Jane Austen adaptation, Love & Friendship, which reunited the stars of The Last Days of Disco in the director’s first true period piece.

In advance of his visit to Portland for a 35th anniversary screening of Metropolitan, Stillman joined Oregon ArtsWatch for a wide-ranging conversation about his beginnings as a filmmaker, his discovery of young talents, his love of dancing, and more. Metropolitan will screen on Thursday, May 1, at Cinema 21, with Stillman in the house for a post-film discussion and Q&A. The interview has been condensed and edited for clarity.

OAW: Just to get this out of the way, my middle name is Whitney as well. So we’ve got that going for us.

Stillman: We must be cousins or something.

OAW: So, before making Metropolitan, you never attended film school or had any formal training, correct?

Stillman: It’s a pathetic story.

OAW: Oh, good. [laughs]

Stillman: The only thing I did at Harvard was get in. After that, I was turned down for absolutely everything. I guess they could spot someone not very academically serious. The two big Himalayan tasks, I guess there were actually three, in college were to get on the newspaper, which was incredibly grueling and masochistic. I mean that we were the masochists, they were the sadists. We were tortured by all these people who became big-deal journalists later on. Finally getting on the newspaper was one thing.

Then I tried out for Hasty Pudding shows. That’s your musical comedies, I felt that Damsels in Distress was finally my quasi-Hasty Pudding show. I could never get into all the film programs, film courses, or seminars. I was just totally rejected. I couldn’t do anything at Harvard. It was pretty artsy-fartsy, very obscure. I mean, not my cinema orientation.

There’s actually a good movie about it. [It’s called The Windmill Movie.] Alex Olch, who helped found the Metrograph Cinema in New York, completed a documentary started by the film teacher at Harvard. The film teacher was a guy called, I think, Dick Rogers. He was a graduate of my frat. I occasionally saw him come by the clubhouse. I couldn’t get into his course. Only beautiful girls that I knew seemed to get into his course.

OAW: [laughs] Curious.

Stillman: The voice of one of them is in the documentary on an answering machine. She also was on the Harvard Crimson, very popular there. The beautiful girls did seem to have advantages at Harvard in my day. She actually made a feature film way before I did, too, because she was also the girlfriend of many important filmmakers. I was excluded from all that. This is a long narrative.

OAW: No, no, it’s good. It’s interesting.

Stillman: So I struck out in cinema at Harvard. I did take a night course at NYU, through the Continuing Education Extension School, whatever they call it. I took Film Production 1. Part A, which is the film part, was the first semester. Then I was sort of a cheapskate. Film Production part B was the sound part, and I wasn’t sure I wanted to take it. When I finally decided to pop for the cost of the course, they were already booked up. So, I didn’t do the sound part. I did just the first semester of Film Production 1.

Spike Lee made fun of me when I started getting attention, because I hadn’t been to film school. It was a real problem at the beginning of the Metropolitan shoot, because I hadn’t had headphones on to listen to what the sound recordist was recording, and it was really bad. The sound recordist was shy and a nice guy. He didn’t want to bother us when he wasn’t getting the right sound. You really want an annoying sound person who lays down rules and said, “You’ve got to worry about this and you’ve got to figure out how we can get good sound here.”

OAW: They’ve got to be willing to tell you when you’re making a mistake.

Stillman: Yes. I was really helped by the greatest cinematographer for leading a first-time filmmaker through the steps. He was a guy named John Thomas, and we were both advertising in the back of the independent cinema magazines in New York, trying to get our first features off. We pooled our ambitions and he walked me through everything. I mean just really rudimentary stuff, like he’d say, “Now these two characters walking towards us, you want to see them from head to toe?” I’d say, “Yes, let’s see them head to toe.” He’d say, “But they’re really, really tiny. Don’t you want to take them from the waist?” I’d say, “Yes, let’s do that.” Over and over again. He walked me through all this stuff and it was really, really helpful.

Then on the second film, we were really pressed for time at a certain point. We were in this restaurant and I said, “Well, let’s just go into the two-shot on this, let’s not do a master.” He was shocked, because until then I had my training wheels on and I’d do the master shot and then the two shots and then everything. I just realized that we were just not going to finish the film if we didn’t start going right into the two-shot.

OAW: Is that a process of you getting more and more comfortable with seeing the finished film in your head and being able to know what you’re going to need and what you’re not going to need from an editing perspective?

Stillman: Exactly. That was it. I knew that I wouldn’t need the master and it would be boring and we’d just go right into a two shot. I wish I had made more films. I still hope to make films, but I think there’s this tension between increased knowledge and the temptation to be less rigorous. I don’t think experienced filmmakers—Can I use ipso facto?

OAW: Of course.

Stillman: I don’t think experience ipso facto means you’re going to make a better film, because there’s this tension of keeping your discipline and not cheating and not doing the easy thing. You see it with acting when sometimes you audition a TV actor and you think, “Oh, gosh, this is really good.” You hire the TV actor over the film actor because they know how to audition, know how to make it seem pretty good, but it’s not going to ever change from pretty good with tricks. Another kind of actor, less facile in that area will flail around and look not so good initially, but they’re working towards something that’s a greater goal. I think there’s this tension between knowing stuff as a filmmaker and then shriveling your standards down as you go.

OAW: Only the greats are able to walk that tightrope, right?

Stillman: The thing that’s extraordinary about my favorite filmmakers, the ones I really admire, people like John Ford or Alfred Hitchcock, is that during the height of the great studio era, a lot of people were making good films, but only the really great filmmakers of that kind kept making good films after the studio support staff disappeared. They had their own studio of the head.

OAW: That’s a great phrase. The current season of the podcast You Must Remember This is about that very topic, the work that great studio directors did later in the careers. It’s very interesting.

Stillman: Another of my hobby horses is how great the cinema of the first half of the ‘30s was. It’s incredible, the economy! I just had a Twitter fight with some guy who was damning all films made before something like 1990 as being slow, and it’s so untrue. Films of the early ‘30s, in like a 70-minute film, they’d have just so much story, so much stuff happening.

OAW: Yes, and there’s so many of them. And they’re just amazingly, like you say, efficient. All killer, no filler, right? I’m a huge fan of that era as well. Getting back to your films, I read an interview you did with Andrew Bujalski a few years ago which dovetailed with something I was thinking about re-watching those films and how they were part of this late ‘80s, early ‘90s American independent film movement that was very much about young people talking. Whether that’s Richard Linklater or Kevin Smith or your films, or later the mumblecore, quote-unquote, stuff. I was curious whether you see them as part of that tradition, since in other ways they’re very different than some of those films.

Stillman: Those things make it seem like there’s some movement in the ‘90s in the same direction, but there didn’t really seem too much of a movement at the time. I really felt there was much more of a Quentin Tarantino, [Robert] Rodriguez thing where they’re going off on this gun thing, this cool guy thing. There’s only poor Noah Baumbach who was doing stuff like I was doing. We were pretty lonely.

Mumblecore was like, oh gosh, finally we have a Rat Pack. Finally, we have a group of people doing something similar to what we want to do and also the same sort of lack of money. It really helped me. When I was doing Damsels in Distress, I had very little money but more than they had, and so I could hire people from that world. The producer smartly said that the budget was much higher than it actually was because it keeps the distributor motivated to earn the money back. I wanted to say how cheap it was because I was impressed as a filmmaker by how cheap I could work, but that really helped. So I hired mumblecore people, and Greta Gerwig was the Barbara Stanwyck of mumblecore or the Bette Davis of mumblecore or, no, the Irene Dunne of mumblecore, that would be it.

OAW: I’m sure you’ve been asked this before, but did she stand out in such a way that you were unsurprised to see her become this auteur figure and cultural force?

Stillman: One of the things that really impresses me, and I didn’t really realize it at the time, is that when the industry decides that someone is the hot comer, that someone is going to be big. I remember when it was Ben Affleck and Matt Damon were going to be big. Everyone said, wow, these guys are going to be big. Then I remember when I was casting Damsels in Distress, it was that Lena Dunham and Greta Gerwig were going to be big. Boy, was that true. Aubrey Plaza, too.

The industry really does know what’s happening. The advantage for me was they got Chloë Sevigny wrong. I don’t think people realized how great she was going to be. That helped me having her available for Last Days of Disco. All the casting people were very cynical about Chloë back in the day because she was not a “real actress.” She had just been roped into Kids and blah, blah, blah. I think Kate Beckinsale also was spotted as an upcoming star really quickly, and Mira Sorvino. The industry really knows who’s going to break as a star.

OAW: It’s interesting because it’s a little bit of a chicken or the egg, right? They’re also the ones who have the power to make someone a star. They can’t force anyone down the public’s throat, but they pick someone and then they have some ability to make it happen. Fortunately, in all the cases you mentioned, they promoted people who are talented and unique. That’s not always the case.

Stillman: I think it’s more egg than chicken. I really think these people do have something amazing and the industry has spotted it. I think it’s more than just the industry making opportunities for them.

OAW: This is the 35th anniversary of Metropolitan. You did some screenings for the 25th anniversary, and I was curious if revisiting it in 2025, does it hit differently now than it did, say, 10 years ago?

Stillman: When I go to the screenings I normally come in for the last 20 minutes of the movie, often during the scene with the older guy at the bar. I used to think that there were four protagonists in the film doing different things. There’s Audrey, who’s a key person. The heart of the film’s point of view in a good way. There’s the cliché outsider character who brings you into the world, which is Tom Townsend. Ultimately, we don’t identify with him completely. Then there’s the sardonic wise guy played by Chris Eigeman. And there’s the sociologist talking about social decline in Doomed Bourgeois, played by Taylor Nichols. Now I think the fifth protagonist is the man at the bar. I think he’s really important to the film. That’s a non-actor named Roger Kirby. He was an ex-boyfriend of my sister’s. He went to school with Oliver Stone and Lloyd Kaufman. Do you know Lloyd Kaufman from Troma film?

OAW: Sure. Absolutely.

Stillman: They were the trio in their school in New York. My sister said at some point, “I only know two film directors, you and Oliver Stone.” Anyway, so Roger was also one of our location guys. I mean he’s an incredibly smart, fearless guy. But he over-rehearsed and he was just reciting the script. I was thinking this scene is going to be useless.

The editor, another person I learned from, Chris Tellefsen, had a really interesting idea. Whenever Roger was moving his drink or sipping his drink, he was relaxed. Chris just edited it with him drinking a lot, and then put a lot of the scene over the two young actors. Playing it on them, and with Roger more liberated with his drink, the scene really worked. It’s great to see what editors can do. They’re probably the smartest people. I guess some of the writers are smart, but also the editors are really smart people.

OAW: The three films, Metropolitan, Barcelona, and The Last Days of Disco, have each been seen as all being about the end of an era of one sort or another. I’m curious about that in light of the era that we’re in now feeling like the end of something. I wonder if those films read differently or are applicable to our current, capital-S situation. You’ve always tried to avoid being overtly political, and I wonder if that’s still true. To what degree do you think they speak to our current dilemma?

Stillman: I don’t know. I don’t think they do. Maybe that’s a good thing. I think Barcelona was the most political one, and I guess it deals directly with a lot of issues today because it talks a lot about NATO. It seems like we’re on the wrong side of history now. That it’s just the world upside down from where it was when I was making Barcelona. I think that Metropolitan and Disco have that “end of the era, this is all going to disappear” spirit. I think although we refer to the end of the Cold War in Barcelona, it’s not an elegy. I think it’s a different kettle of fish.

Also, Metropolitan and Disco have the same sort of frivolous group aspect. It’s dancing and festive and drinking, all that kind of stuff. Dancing became important for me and for the films, and it’s still something I really like and care about. If you’re making a romantic comedy, what can you have that’s cinematic and interesting where they’re not talking? It’s music and dancing that does that.

OAW: To use them in a way that communicates character and advances narrative is a neat trick. Those scenes do that really well.

Stillman: This is something interesting about how important dancing was in the past. It’s incredible how little dancing there is in the contemporary world. It’s like that René Clair film, Under the Roofs of Paris. If they go to a bar, there’s dancing, if they go to a restaurant, there’s dancing. They’re in the streets and there’s dancing.

OAW: And this is in 1930 Paris during the Great Depression. If they could dance then…

Stillman: It’s also true that that generation has died. When I was a kid during these parties, the really good dancers were the grandparents. They’re long gone, but they were the people who grew up in the ’30s knowing how to dance well. My father just loved doing the polka. Who does polka anymore?

OAW: [laughs] I’ll let you go in a couple of minutes. I appreciate how generous you’re being with your time…

Stillman: What’s the cinema like? Is this a good cinema?

OAW: Cinema 21? Oh yes, it’s great.

Stillman: How long has it been around?

OAW: Oh, forever. I moved here in ’91, and it was going strong.

Stillman: Do a lot of filmmakers still come through on Portland? Because Portland was on the trail when the films first came out. I think that I came with Metropolitan or Barcelona or both. Then it dropped from sight. They were not programming a trip to Portland anymore.

OAW: Well, with the changes in the local newspaper industry and the other larger structural changes in film distribution and especially indie film distribution, the scene suffered a bit in Portland in terms of trying to get adventurous and interesting programming to town, although I think we still punch above our weight. It’s been a struggle, honestly, and Portland itself, as I’m sure you’re aware, has taken a bit of a hit reputationally in the last few years.

Stillman: Is it coming back from 2020? I mean, has it gotten better since 2020?

OAW: Yes. It’s gotten better, for sure. There’s always still work to be done. I think you’ll enjoy visiting.

Stillman: It’s really been great. Thanks very much. Any last stuff or are we—

OAW: Yes, let me ask you. I glanced at your Twitter feed and I saw that Richard Brody was suggesting that you do a Great Gatsby movie, now that the book is in the public domain. I just wanted to say I think that’s a fantastic idea.

Stillman: That was a great tweet. I don’t really want to do a Great Gatsby because it’s been done quite a bit. Also, I looked into adapting Fitzgerald. It’s a lot like catching water with your hands. It’s beautifully ephemeral. I hope to do something in those lines. What was ideal for me was the Jane Austen book [Love & Friendship] that was not really finished by her and obscure. It seemed like something I really could make a contribution to rather than just destroy a pretty work of literature.

OAW: I know you had a flirtation with doing a show for Amazon, and without getting into the details of that, are you committed to doing future work for a theatrical release? Or would you be open to TV/streaming stuff?

Stillman: I want to focus on feature films. I really wasted tons of time trying to do TV. I think the seeds of what we had in The Cosmopolitans will become a very different kind of feature at some point. I hope that work is not lost. It’ll pay off. Then I hope to do a couple of other things, God willing, as they say.

OAW: Excellent. I look forward to seeing whatever emerges from that process.