Nearly 24 years ago, Chris Wilcha premiered his debut feature documentary, Target Shoots First, a fascinating personal essay shot on a Hi8 camera gifted to him by his parents. The NYU philosophy grad leveraged his experience working at Flipside Records in my hometown of Pompton Lakes, New Jersey, to score a position at Columbia House Records, where he was tasked with selling the subscription service to Gen X. Decades (and many ups and downs) later, Wilcha has returned to explore his life’s creative journey with the self-reflective Flipside, a TIFF selection which recently had its U.S. premiere at DOC NYC.

As Christopher Schobert said in our TIFF review, “Flipside starts as one thing and becomes something very different––a study of regret, the failures of nostalgia, and the value of seeing and (occasionally) preserving. (It’s also about the necessary act of throwing things out, eventually.)

We spoke with Wilcha after the film’s U.S. premiere about capturing his personal journey, the fascinations and hardships of northern New Jersey, his experience on This American Life, and the state of documentary filmmaking and distribution.

The Film Stage: Full disclosure: I grew up in Pompton Lakes and was so excited to see the film, even if I feared it might not be the most flattering portrait of the town.

Chris Wilcha: To be honest, there was a section about DuPont [Note: a contaminated swath of land that a successor corporation has since remediated]. But it just got too complicated. There came a point where I had too many ideas. But as you know, DuPont’s history is quite insane there.

It seems like a theme in this film: you take your eventual wife on a first date to Centralia, PA.

That was a little road trip I took early in my relationships.

In my other career, I’m a programmer for the Buffalo International Film Festival, and we recently had your friend Elisabeth Subrin in town for a screening. She told us you were always documenting things and that you’d send her pictures of something from 20 years ago. But in this film, you’re also navigating the act of letting go. I’m curious to hear about your early impulses to document everything.

I was in college, and something clicked and I was just blown away by what you could do with the medium––the incredible variety of different forms, styles, and approaches. It seemed like this infinite, endless, infinitely open-ended form that you could adapt in all these different ways.

Even back then, documentaries were less ambitious than they are now. I think they’ve gotten so conceptual and, in kind of an amazing way, it feels like a crazy playground of ideas. But I, just early on, realized that everything changes and that, you know, if I go home and I filmed for ten minutes, that is a moment that would have disappeared and evaporated. And I always loved the durational kind of documentaries, like Robb Moss’ film The Same River Twice. Here we all are, and we’re, like, 20 and heading out into the world, and then here we all are and we’re 50. And what happened? I don’t know. Those passage-of-time documentaries always really intrigued me.

I’ve subsequently been hired to do things where you’re shooting the whole thing in a fixed period or doing something for hire. But when it comes to the personal stuff, I think I still follow this collecting instinct where I’ll be drawn to a topic or a person or want to do an interview, and I’ll do it.

Target Shoots First reminds me so much of that period when the promise of digital video allowed everyone to make a video diary––now I suppose, in the era of YouTube and TikTok, that idea is not nearly as novel. The film comes out, and then what happens? Was there a project you were dying to make right after that film?

Well, back then I was trying to figure out how to make a living. I think I was so open. I was shooting anything that would move, music-related and personal things. I remember I did a pilot for a PBS show about design that never saw the light of day. I did another pilot for PBS with a friend where we thrifted across the country in a used ambulance and sold everything out of the back. We assembled that ourselves, and then that was going to be a pilot on PBS. It aired, and it did incredibly well and got fantastic feedback.

The thing about PBS is that they wait to give you the money right away. They have to raise money like all of these things––so it just took forever for that fundraising process to happen––and then it lost momentum, and then it died. I was always running things, but making things happen can be challenging. Sometimes that can be your creative force. But sometimes it’s access––access to a person who just changes their mind.

We made the pilot. It got publicized. It was on the air. We had a party, and then it just sat. But what came after that, like a breakthrough for me personally and creatively, was getting hired to adapt This American Life to become a TV show––that was just, like, an incredible sort of dream documentary job. So that was the next big thing that I did after that, and it was great. It was a unique, memorable, totally inspiring work experience.

It sounds like a cautionary tale. I’m always telling my students and other filmmakers I mentor that what looks like an overnight success at Sundance is a lot of years of hard work and a little bit of luck. But there are other ways of building a fulfilling career slowly.

There is something about being a student, when you look out in the world and you see all these fantastic finished films and it just seems like people’s careers are inevitable. This happens to me on Instagram sometimes, where I come upon a photographer that I’ve never heard of and I’m like, “My God, this person’s work is amazing.” Before you know it, you have decades of fantastic stuff to metabolize and absorb, and they’ve been prolific and productive and that there’s been no unbroken success. There’s a lot of fits and starts.

It is tricky to sustain belief in a project over a very long period when you need more money or support to follow through with it. I wondered if younger people would relate to this film, and we have only had a handful of screenings, but I’ve been pleasantly surprised at how it’s been helpful for them to see people just out of college starting to figure out their careers.

Like you said, it’s almost a cautionary tale in the sense that it’s hard to figure out. I think that you have to keep making a run at it and sustain belief in your ideas against everything else. So I continue. I am setting up a shoot to shoot something next week of my own. You know, no one’s asking me to do it; no one’s paying me to do it. I still have the bug, the obsession, the interest, and that’s what propels me forward. Commercial work is exciting and a fantastic way to make a living, but it also has an intense competitiveness.

I was always trying to figure out how to make a living. Elisabeth is an exciting example. She went the academic route: you teach, get the job, and pursue tenure. That is an incredible amount of work, and you have students who need a lot of energy and attention. Elisabeth is an exciting example of continuing to make work while also teaching. As I say in Flipside, I was surveying the field and trying to figure out how people do this. I remember stumbling on to sort of the Errol Morris model where I was like, “Wait a minute, he’s directing all of these commercials, but he’s using them to either subsidize or at least allow him to then as a counterpoint, to make his films.” And I’ve learned more about how he works: he will shoot a breathtaking amount of commercials in any given year and be doing his films and be doing the writing. He’s an incredible example of a certain kind of work ethic.

I love that the film is so specific about northern New Jersey. I remember Uncle Floyd on Public Access TV. I was surprised to find out that he had national success. That was a treat to find out. He’s so fascinating that he could warrant a whole documentary.

I had inquired about doing something about Floyd, but his manager––and Floyd himself––were not so interested in being the subject of a full-length feature, devoted documentary. So I shot what I could with them; they’ve been very supportive. But they were not interested.

So again, a classic case of: I had the idea, I thought about it, I tried, I pursued, I wrote the love letters, I met with Floyd, and I did the best I could. We got to shoot with them a couple of times, which was the end. But I imagine This American Life was the training camp for that short mini-documentaries capturing what was such a great show.

Totally. I love the radio show and thought it translated beautifully to the screen––I had seen a few episodes in theaters when Fathom Events showed it. I’m curious about the show as a training ground for you.

Yeah, that was a dream job. There’s sort of no other way to put it, to report to work for a few years and get to sit in those story meetings and to see how they construct stories, how they imagine stories, how they brainstorm. It was like a graduate-school seminar. It was astonishing. I would take notes; I was always constantly learning how they do what they do. They deploy tricks and techniques and a house style to certain things, but they also work so hard; Ira’s work ethic is breathtaking, all of them.

But I think he still, even until very recently, is there giving notes on mixes and sitting in sessions with writers and people constructing the stories and delivering messages. It is so much labor and energy and effort, and I feel like I learn so much from those guys. So yeah––it was extraordinary.

What’s also interesting about Flipside is that you offer a rare look behind the scenes at Ira Glass, including some compassionate moments you capture with his one-person show. It pairs beautifully with the Herman Leonard portions of the film as well.

Well, with Ira we went and shot a portion of what he was doing, not exactly knowing what it would be like. Was there a film there? Was there not a film there? In that interview in the documentary, he seemed in a reflective mood that day, and it felt like he said some heartfelt and honest things about how he was feeling at the time.

And to be completely clear: I asked his permission and I wrote to him five or six years later when I assembled Flipside. I said, “Look, I’m using this. Are you okay with it?” He wrote back and we talked on the phone. But he said that if I say something publicly, it’s fair game. I’m from that old school where if I said it in an interview, it is my permission to use it. But he gave me his permission. He signed a release. And, as I think a further expression of his endorsement, he came and did the Q&A at a screening last week at DOC NYC.

Each abandoned project is trying to carry a particular theme or idea, and the hope and the thought was, “Can these voices recur, and can we structure it in a way where you leave a story?” You come back to it or you go to a character, and then they echo some ideas that they’re thinking or that I’m feeling later.

And it was when we cracked the code on that editorial strategy, I felt like, “Okay, I think this might be able to work as an essay, using these abandoned projects as the raw material.” Flipside is a great character, too, as being this kind of mythic creature.

What was it like the first time you went back to Flipside Records? Was it like being home? Was it shocking?

Yeah, it was the first time I returned. The very first time, I was startled at how little it had changed. I would go to a stack of records and I was sure there was a record there that had been there since I left 20 years before. It was so stopped in time that it was remarkable. But then I also saw the sort of powerlessness of that. If something couldn’t change, [owner Dan Dondiego] would recede ever more into the background, like his resistance to social media and being online, and he does not even have a smartphone. All that stuff is charming in a funny way, but it’s also deadly for a small business. It was a combination of the two, and I went there when I returned.

It’s that preservation instinct. It’s that documentary thing where this might not exist in its current state for much longer. And it persisted then, maybe even longer than I thought it would, partially because vinyl has had a little revival. Also because I think Dan keeps things very lean. He’s his only employee. He’s not spending lavish amounts of money on marketing, either. But it was returning to this crazy fountain of youth, and it was also complicated. I wanted to help Dan, and I also wanted to see Dan help himself. He must be interested in only a few current ways small businesses market themselves, like Instagram and online. I almost had a version of this where I was like, “Maybe I’ll come back here and work here for a summer and, like, forgo my life.” But it was too much of a stunt. And by the way: he was not particularly interested in having me around or being saved.

Your publicist sent me a picture of him watching the film on DVD on a tube TV at the store. What did he think?

You definitely should ask him. I’ve only heard back from people who were there. We haven’t been able to talk because I was traveling over the weekend and he just watched it a few days ago. But the word on the street is he gives a big thumbs-up. He fully approves, and I think he gets it. He gets what I was doing all those years.

I knew it took a while because a few storefronts in your b-roll aren’t there anymore––the Salvation Army building is now an apartment complex. I also love that you captured Station One as this accidental record shop. We spoke about DuPont, but I’d like to know if any other threads of North Jersey curiosity almost made it in.

We shot as recently as June. So those montages are a mix of periods and, yes, document things that have since disappeared. But I love northern New Jersey. There’s a whole Bruce Springsteen connection that I couldn’t figure out how to work in. It’s on “Nebraska”––there’s a song about the closed Mahwah Ford plant. Have you ever read that story about how they used to dump their waste in the mountains up there? You can see it like sparkle––purple paint oozing out of the landscape from when Ford used to dump paints and chemicals in the landscapes of New Jersey. I mean, there’s just crazy stuff from, like, Galaxie 500 cars. Do you know what I mean?

I believe it. I remember being in elementary school and seeing whole backyards dug up by Dupont when they remediated the soil.

Because Dan reminded me: we used to hear explosions and they would detonate munitions, things they were using or testing. Think about how strange that is. This munitions plant is poisoning this landscape. I mean, it was such a complicated story, and those houses that border the Superfund site––I feel bad for those people. Can you imagine living so close to essentially a toxic waste dump? I don’t want to get controversial here, but there was a seven-part series in the Bergen Record.

About the plume.

Yep, about the plume. That story persists, and apparently there’s controversy in town. You’d know the story better, but some people want it known and some people don’t want it known because it diminishes real estate values. So it was like, like you said, cracking open a whole other documentary. Like, I wasn’t prepared. It was too big to contain in one of these stories. So again: I find New Jersey and northern New Jersey an endless source of fascination.

Absolutely. What are you working on next? I know it’s a softball question, but will we wait another 20 years for a feature?

Well, I’m already shooting some new stuff which I’m excited about, and some possible hiring jobs might result from this, which could be interesting. I don’t have anything to report. I think what I’ve learned in this process is that things like this are indeed a labor of love and that it is likely that, if I want to continue making things, I will always have to strike this balance between the things that pay the bills and the things you can get hired for, and then the things you want to make.

And you have to figure out what they are and that they could be more suited to a quick, easy pitch. Or a sizzle reel. So I think that I might have to keep working in this mode of making a living as a director and being a working director, shooting commercials and documentary stuff for hire.

But that weirder, more conceptual stuff, I think, might have to stay in the “labor of love” category because it just seems like the documentary marketplace is peculiar right now. There’s a lot of films that got made in the last couple of years that didn’t sell at the previous couple of big festival outings, and so I think it’s a really strange time to figure out where these things might have a home, unless it’s super celebrity-driven or spectacle-driven or true crime.

There is less space for personal documentaries unless they’re immediate crowd-pleasers. But I love your film––and it seems like it had a happy ending, even if you’ve taken some detours.

And the David Milch chapter is a fascinating insight into another way that a creative person was working. His life was a lot more complicated, and I am in no way comparing myself to David Milch, but the work completely consumed him to the point where it erased many other things in his life. But I would like to make more long-form documentary work more often. We’ll have to see how next year’s distribution plans play out.

Is there anything else you want to say about the film?

This was not a solitary effort, and that was the only way it got done. It was with the producers who got involved and decided it was worth pursuing, and the editor I hadn’t worked with in a long time became available. Even friends came onboard; a friend helped me co-write it, and he also composed the music. It was like the indie labor-of-love model where you recruit everyone and can’t pay them what they’re worth or their rate. But everyone still believed that it was worth doing, and everyone feels really good that it’s finding its way in the world.

Flipside screened at TIFF and DOC NYC and is seeking distribution.

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