Who are the lead actors Andrew Von Urtz (pictured) and Cindy Chastain—friends of yours? Did you write for them, or settle on them after the film was written?
Yes, Andrew and Cindy are both friends of mine, we all went to film school together. Before Loveless, neither of them had acted in a feature film. I wrote the script for Andrew, the character and many elements in the film are based on his life. Andrew and Cindy were once a real-life couple, they met as undergraduates and at one point they lived together. At first I looked for other actresses to play Cindy's role, "Joanna," but one day my wife/producer, Shauna Lyon, and I ran into Cindy on the street, told her about the project and she said she'd love to be a part of it. At first I wondered what kind of emotional damage I might be tapping into, but I was excited about the idea of having Andrew's real-life ex-girlfriend playing his ex in the film. They have a great natural chemistry, which led to better performances.
The disclaimer at the end credits cheekily refers to the film as “somewhat fictitious.” Is the film, then, inspired by your and your wife’s own efforts to secure financing for your independent films?
Yes, the film is definitely about our struggles as filmmakers, but especially as filmmakers of a certain age, who were around to witness the rise of independent film in the 90s only to see it lose its cultural status and commercial power. Some would argue that, talent-wise, there has never been a better time for independent film, but it's so much harder to make a living at it. So Loveless is not just about a filmmaker, but specifically a Gen-X filmmaker who is finding out the hard way that the world has changed.
Should we read an extra layer of reflexivity into your own presence opposite an aimless filmmaker friend?
Yes, the reflexivity gets a little out of control when I'm on screen. I'm playing a version of myself and Andrew is doing double-duty, playing a version of himself and yet another version of me. I don't expect people to care about that stuff, although it's nice when they do. What's most important is that people see how much Andrew freaks out when I make him hold my baby; that's a defining moment for his character.
The “plaster of Paris bagel with cream cheese paperweight” line is an obvious (as obvious as these things go, anyway) reference to After Hours, and an apt one, given how your prickly protagonist chases an unstable pretty girl downtown and gets in over his head. (Another movie that came to my mind was Rosemary’s Baby: a selfish struggling artist makes a Faustian pact with a batty/sinister, possibly supernatural enclave of long-time property-owning Manhattanites.) Were there any other films you watched going into making Loveless?
I think I was influenced by how Woody Allen handles urban relationships with a blend of pathos and absurd humor. But After Hours is the only specific film that we watched and talked about; it also happens to be the film which inspired me to move to New York and go to film school. In honor of After Hours, we shot a few scenes in SoHo at night and, while looking for locations, I tried to find streets which retained the dark and rough character of the neighborhood in the 80s. But then I realized that if Loveless were to serve as an accurate record of my generation then I should present SoHo as it exists today, so we chose to shoot in front of some of the luxury boutiques which have taken over the neighborhood.
The film is a great portrayal, I think, of friendships at a stage where people are just starting to live with the permanent consequences, good or ill, of their choices—“We’re adults now!”, as one character, Tad, says—and so there are so really mismatched sets of friends we meet. How much of a backstory did you fill in while writing?
There is a lot of backstory which is only hinted at in the film, especially regarding the Tad and Joanna characters. Tad is based on a real guy named Tad, who actually makes an appearance in the film. In fact, in the scene where the real Tad makes an appearance, he is sitting right next to fictional Tad. It's another one of those inside jokes which keeps me amused.
I’ve seen a lot of movies, in the last few years, about men who’re avoiding committing to a relationship, or a career, or any of the other compromises that come with a future. This guy is getting older, too—in Greenberg and Uncle Kent and in this one, he’s middle-aged. Why is the fuck-up becoming such a universal icon?
I'm friends with Joe Swanberg and Joe knows Noah Baumbauch, so maybe there's some kind of psychic connection going on? Seriously, maybe it has something to do with our economic times and the realization that we're not going to be better off than our parents. I'm not sure, but A.O. Scott wrote an article identifying a new mini-phenomenon of films and books dealing with Gen X facing midlife crisis. This seems like a natural development and I'm glad to be a part of it. The Baby Boomer narrative has been so heavily covered over the past few decades that it feels good to be able to represent my own generation.