Dick Rogers was your film teacher at Harvard - how did you end up making a movie about him?
He was my mentor, and he was producing the first film that I was making after college. And we applied for a grant together, had the money together, we were all set. He was producing, I was directing, and then he got ill. The project sort of fell apart [after Dick's death], and I was looking for another film to do. I was trying a bunch of other things, and then this Windmill project came along, and at least on a personal level, it sort of felt like a way that I could still make a film with Dick.
You get such an under-the-surface look at him in the film - what was he like as an everyday person?
As a guy he was one of the most charming men that I think most people that knew him had ever met. He was remarkably witty, remarkably intelligent, remarkably insightful, and he was very good at creating close relationships very quickly. So I just assumed that this guy was so charming that making a movie about him would be easy. It actually proved to be a lot more complicated than that.
You had almost 300 hours of footage to sort through - how did you deal with it all?
It really started very organically. After he died I was briefly in touch with [his wife] Susan, and she asked me to come by because his Avid editing computer had broken. So I figured out how to plug in the hard drive, and up came this project. And I asked her, oh, what's in here? And she said, "Well, it's this film. We're not quite sure how far along he was with it. What are you doing for the rest of the day?" And so I watched some footage. At the end of the day I showed her some things, and she said, "What are you doing for the rest of the week?" At first I was just going to cut together some footage for his friends, who were curious about the project. It was only after going through all of the hundreds of hours that I thought, "Maybe there's something more interesting here." Once I decided that there was a portrait that could be made, figuring out actually how to make it was massively more complicated than I ever imagined.
What made it so difficult?
He was torn from the very beginning. He goes out to this place in the Hamptons, he thinks he's going to be making a film about this place, shoots all this beautiful footage of this place. He doesn't want to put himself in the film because it's too self-indulgent. Yet all the footage and all the scenery is only interesting because it relates to his life. So, he's kind of painted himself into a corner of making this autobiography that he doesn't want to make. And there was no plan for what the film was supposed to be: no existing cuts, no script ... There was a folder that said, "beach," and in the folder was twenty hours of footage of the beach. And there was a folder that said, "softball," and it was five hours of clips of people playing softball. So there was no real plan that I could go by. The big decision for me was: I wasn't really wrapping up a film that he couldn't finish ... I was making a portrait of this guy who was trying to make a film. And once I figured that out, I at least had a sense of where I needed to go. But that still took a lot of trial and error work. At this point it's been basically six years.
Were you shocked to see his dark thoughts and insecurities once you opened the can on all that film?
The big surprise was that when he was being filmed and he was getting funnier, or light, he literally would tell people, turn the camera off. So there was a sense from him - cinematically at least, for the purposes of this film - that the funny side of himself was not something that he wanted to take seriously. So there was a weird way that he was kind of editing parts of himself out of what he was shooting. And that was the surprise, because most of us knew him to be so charming. So the cards I was dealt, in terms of what footage he left for me, were definitely a lot more serious, a lot more personal, and a lot more revealing than I would have thought.
Why do you think he cut that side of himself out?
I think he was trying to make a good film, and the tricky part about making a film - especially for a guy like him, who's made 18 other good films - is you train yourself to look through the eyepiece and out into the world. The one thing that technique doesn't train you to do is to turn the camera on yourself, because literally you have no experience looking at yourself. All the tools that are normally at your disposal as a filmmaker are not quite as applicable, because you don't have the ability to get any distance from yourself, and so a lot of your decisions, which would make a lot of sense if you were documenting somebody else, might not actually be such smart decisions in terms of how to document yourself.
As the years went by, were you worried that you'd inherited your teacher's doomed film and would also never complete it?
Absolutely. Working on it for all those years, being a first time future film director, living in New York, I certainly felt the pressures of friends saying to me, "Oh, you're still working on that documentary?" And I could certainly relate to, quite intimately, that feeling Dick had of people asking about the film, feeling embarrassed that the film's not done, scared that the film's not going to be good. So that was a very, very close connecting point.
Now that it's all over - how do you think you've changed over the course of the project?
It's interesting for me. Six years ago I was an ambitious fiction film director, and I was finishing a script that I was ready to do. And then this bizarre afternoon happened where I watched this footage and got involved in this project. So now, six years later, as I go back to working on that script, I find I'm in a different place a little bit, that something has happened in the making of this film that has definitely affected me as a filmmaker. So the next project is a purely fiction film, but my sensibility of what makes for good fiction is now deeply informed by non-fiction documentary - and all the things that were swirling around in Dick's head.