With Flipside, Chris Wilcha Made a Triumphant Film About Failure

Chris Wilcha has not fully absorbed that his new movie will be in theaters soon. “I had this moment today actually,” he tells me Tuesday over Zoom from his Los Angeles home. “I’m getting on a plane to go to New York tomorrow for the first screenings. I was like, ‘I almost can’t believe I’m putting this out.’”

The bewilderment is understandable: The fiftysomething filmmaker and commercial director has spent a good percentage of his career not finishing movies. But soon, audiences will get to see “Flipside,” which Wilcha rightly calls a labor of love. It’s a documentary that has been years—and many misfires—in the making. At the start of this century, Wilcha released “The Target Shoots First,” a sly documentary about his experience working a soul-sucking job at Columbia House, struggling to maintain his artistic bona fides while taking a paycheck from the Man. That self-reflective film helped launch his career, but in subsequent years, he discovered that he’d need to continue doing jobs that weren’t dream projects—specifically, shooting commercials—to support himself. Along the way, he enjoyed his share of creative fulfulfilment, winning two Emmys as director on the television version of Ira Glass’ beloved “This American Life.” Still, he also watched promising ideas—like a documentary about renowned photographer Herman Leonard—fall by the wayside. Also, life happened, including marriage and kids. Is this what he’d imagined his career would look like when he was an ambitious twentysomething?

All of these thoughts coalesce in “Flipside,” which takes its name from the suburban New Jersey record store he adored and worked at as a kid. Flipside is still hanging around, but it’s struggling, and about a decade ago, Wilcha decided to make a documentary about the place. Except, like several of his projects, the film eventually fell by the wayside. The now-completed documentary is, technically, about the store. But it ended up being about a lot more: the desire to collect things, the Gen-X fixation on not selling out, the difficulties of a healthy work-life balance, the allure of nostalgia, the need to let go of your youth, and the acknowledgment that failure is part of life. With Wilcha as our guide, “Flipside” ruminates on aging and regret, incorporating elements of his aborted previous projects woven into the documentary’s musings on legacy and the impermanence of everything.

“Flipside” has only played a few festivals, so Wilcha is still wrapping his head around talking about something so close to his heart—it’s really a movie about him, and he’s feeling a little vulnerable. “I’m terrified,” he admits about the reaction “Flipside” might provoke. “Like any sane person putting something out that’s personal, you’re waiting for some cruel takedown.” Below, we discuss how quaint a concept “selling out” was, having to still hustle at his age and the phenomenon of living with disappointment while still being happy with the choices you’ve made.

“Flipside” wrestles with a lot of ideas, but I came away from it thinking, “Oh, this is a movie about how we all have to contend with disappointment and failure.”

That’s what I was trying to negotiate, these feelings of this midlife assessment where maybe everything didn’t go precisely as your 25-year-old self may have imagined. Of course, there’s some real disappointment there, but I will say, as a person who’s been carrying around a lot of these [unrealized] projects for a long time, that is also mixed with a lot of joy that it [finally] got done. That’s a plot point of the movie, the fact that I was able, with help and accountability from the people that I was working with, to get the damned thing done. So there was some measure of relief in that. But this thing is tinged with second-guessing and self-reflection.

Did it weigh on you that you hadn’t completed these earlier projects? Was it something you took personally, like they reflected negatively on you somehow? 

When you’re pursuing these things, there are reasons that they all fail. Some of them are failures of creative will—I definitely know what that feels like. Sometimes, it’s that your access was denied. Sometimes, it’s that the money falls apart. For each individual project, I could rationalize, absorb, or digest the disappointment of it. 

But every year, sometime around late November or early December, I would start to have this feeling of “Another year has passed, and I haven’t made film X, Y, or Z.” And it really wears on you after a certain point. There’s a fake symbolism to turning 50, but it felt milestone-y. I was trying to resist the cultural clichés of that, but it got under my skin. I had this pressing sense: "If I don’t [finish] this now, I’m never going to do it. I’m not going to have the energy. I’m going to be distracted with other things.” So I carried with me year after year of disappointment about not finishing much of this stuff.

I was having a busy decade-plus of having a family and trying to build a career as a commercial director, and it was when I started to reflect on these unfinished projects, I was like, “I still feel like some of these things have life in them. I still feel like there’s ideas floating around in these things that maybe even gained a little significance with the passage of time.” But I didn’t want [“Flipside”] to just feel like a bunch of leftovers thrown together—that was a big fear of mine. So what was exciting was the editing process of seeing, “Hey, wait a minute, is there energy still in some of this footage? Do the characters talk to each other in unique ways? Can we have the characters' voices recur over the course of the film?” 

The subjects you chose to follow in these abandoned projects—writers, photographers, artists—do they say something about you? Do those films have a unifying thread?

An essential fact of them is me asking questions about my obsessions—how to balance art and commerce, be a good parent, and be a good husband. It’s biography by other means—it’s displaced memoir. But at the same time, I was not interested in just personal, narcissistic navel-gazing. I was trying to ask bigger questions about how to have a creative life—and how to do creative work that feels meaningful—but also how to make a living. It’s getting harder and harder to balance those two things. I mean, the documentary marketplace seems like it’s in some kind of crazy shambles in terms of being able to make small personal things like this. 

In the film, you mention that directing commercials pays the bills, but you have misgivings about how they distract you from your own projects. Is there any artistic upside to that work? 

After I paid some dues, I started to get better work, and my creativity got better. I got to collaborate with unbelievable filmmakers and production designers. I’ve shot three or four Apple projects with Emmanuel Lubezki—Chivo, the mythic, legendary cinematographer. To sit in a van with him location scouting and asking him questions about Terrence Malick, I’m giddy—that is such an insane privilege. I’ve worked with wardrobe stylists and people in the business and do commercials to balance the off-season or the strikes, and I have gotten to see how they work. I’ve gotten to work with extraordinary DPs. I feel like, all that, I got to bring back to the documentary stuff.

Also, to be thrown into circumstances like shooting internationally—I was doing a run of work for Apple where it was just like, “You’re going to shoot in China, Japan and India.” Working on that scale with those kinds of budgets … there is incredible creativity.

In “Flipside,” you talk about being a member of Gen-X, a generation that puts a lot of stock in artists, never selling out. But that was a different time in which there was an economy that made such a purist mindset possible. 

Looking back, it was quaint that that was even an obsession of Gen-X. That was a fixation because there was a lot of economic abundance—there were jobs. That whole economy has been erased in the years since then. 

When we were making this, I thought about musicians and writers and the devaluation of what they do. I have so many friends who left college thinking, “I’m going to be a writer for a music magazine,” and that whole world doesn’t exist anymore. My friends are musicians who thought, “I’m going to get into composing for advertising and movies because that’s an alternative to being in a van and driving across the country.”—A.I. can now generate those songs in minutes with a few prompts. 

I feel for everyone right now—and I’m still feeling it. This is the crazy thing—I am still just a freelance, dues-paying director trying to make a living. This film was a labor of love. So many people put time and energy into it, and I could not pay them their proper rates, and I’m feeling that. I wish there was some streaming payday where I could have made everyone whole, but that’s not how this is going down. 

I thought there was a moment where you got to coast [professionally] a little, but I am still only as good as my last job. I end a job and I am unemployed—I’m hustling for the next one. I’m not looking for sympathy—this is everyone. One thing I got very sensitive to with younger millennials was the selling-out thing because they had to brand themselves—they had to be on Instagram and social media promoting what they do relentlessly because that’s how you get the work. So I never felt cynical toward them—I never felt some smug Gen-X superiority because I was like, “Oh my god, this is so much work just to get your voice out there.” 

So, the “no sellout” mentality is dead. But are there other aspects of Gen X that you still hold onto?

I still feel prickly about things—like privacy stuff with social media, just giving over photos or information, or when you accept the terms [and conditions], knowing they’re going to own this in perpetuity. I still am suspicious of a lot of stuff. I’ve gotten very involved in tech stuff with my commercial directing work—these bigger companies like Meta or Apple or startups—and you see a world-changing utopianism being sold to you. I often am like, “Something seems off about this.” It took me a while to even start posting on Instagram because I was like, “Wait, I’m generating your content that you’re then monetizing?” That’s such a Gen-X dubiousness of “What is the Man doing?”

You worked at Flipside as a young person. Most of us associate record-store employees with “High Fidelity.” Were you the snobby gatekeeper or the enthusiastic geek? 

We were not into intimidation—we were dorky enthusiasts. What was fun about it then was that it was the internet—this was your community. People would come in and just want to shoot the shit about new releases. We’d read articles and we would obsess over band members and artwork and liner notes. It was the chatroom in real life. It was a place of pure playfulness. 

Sometimes, a person would come in and want some Barry Manilow [album] from 10 years before, but there was no snobbery. It lacked the New York City condescension—right over the George Washington Bridge, we could go to Bleecker Bob’s and be looked at with total disdain. Those New York City shops were way more intimidating—they were way more judging you as you put down your purchases, and you got a smug, dismissive, condescending remark on the way out the door for your naive, clichéd taste. But [Flipside] was enthusiastic, infectious love of music, sharing information, turning people onto things: “Hey, I like this—you want to talk about that?” 

You talk about being a collector, holding onto things like old records and band T-shirts, and then working through the process of giving things away now that you’re in your 50s. Is that letting-go process also about acknowledging you’re not a kid anymore?

Sometimes, I would look at the stuff and feel this rosy, warm feeling toward it. But as the years started to pass, I started to feel like it was only a reminder of my age—that it was just a gauge of how old I’d truly gotten, that these things were just receding further and further into the rearview mirror of relevance. 

One of the themes that I hoped would come across [in the film] is that there was this idea of what you take with you and what you leave behind. That’s the stuff [in my] closet, but it’s also ideas like selling out, interrogating that midlife, and going, “Wait a minute, why did this continue to weirdly haunt me in the back of my brain with some critic sitting on my shoulder judging my choices? Maybe it’s time to let that inner critic go.” I was feeling a lot of feelings in that purging process.

Was there anything you purged that you now really regret not owning?

Some records that I got rid of, I just thought, “Oh, I can stream them; it’s not a big deal,” but I was on eBay the other day [wondering] if I should rebuy an original pressing of Minutemen’s “Double Nickels on the Dime.” I have a CD version of it, and I can stream it—I was like, “I don’t need the thing”—but now I’m kind of regretting it, and I might rebuy it.

If you buy it back, are you not learning the lesson of the importance of letting things go?

I will say this: One breakthrough thing, in terms of owning a phone with a really decent camera on it, is that now I photograph things instead of buying them. I’ll go to a garage sale, and I’ll see a stereo console that I know isn’t even that good, but my inner 16-year-old wants to buy it, wants just to have that piece of technology. But now, I take a picture and step away—I don’t buy it. I don’t need a storage space to put it in to then pay to own it. I have found photographing things—records, clothing, vintage artifacts, objects—liberating. I can still document it. I can appreciate it in a certain way. But I often don’t need to own the actual thing.

This is not a Gen-X thing, necessarily, but there’s a certain artistic mindset that believes, “I can’t have a family, I can’t settle down because my art has to be the priority.” That is not the mindset you’ve adopted, but I wonder if that was a struggle initially when you started having kids with your wife.

Much like [with] aging, I think we sometimes think we’re the person who is going to get away with not having these things happen to us. There was a, perhaps, diluted optimism when I was at a particularly giddy, youthful moment of considering having a family where I thought, “You know what? I think I can pull this off!” We had both of our kids right while I was doing one of my favorite directing jobs I’ve ever done: a TV version of “This American Life.” We had these young kids, and I had this TV series that won a couple of Emmys. I was actually making a living doing [that show]—it wasn’t just cobbling together freelance things. I thought, “This is amazing.” 

But the problem is, it is a marathon—it is not a sprint—and then what you realize is that sometimes it’s happening invisibly, the choices you’re making. You're making a choice to spend time with the family and maybe not pursue that job or not spend extra time writing that treatment. That conflict is a central tension for anybody trying to make a living, have a family, and have a creative life. That’s a little bit of what “Flipside” wanted to examine—there are sacrifices that go along with that. 

Maybe I didn’t make as many documentaries as I’d hoped to, but I also feel incredibly close to my family. we’re intact, and my daughter just got into college. It’s a daily struggle: Every job I get, how long is it going to take me away from things? What are you going to miss in the process? The whole endeavor is tinged with sadness, but part of adulthood is holding these contradictory things in balance—that you can live your life, but you can also have some heartbreak simultaneously. It’s all blended together.

In your film, legendary jazz photographer Herman Leonard reflects on the fact that, wow, maybe he actually did good work. It took him the end of his life to come to that obvious conclusion. Do you think you have a body of work?

I would like to make a couple more long-form documentaries. I want to shift some energy toward pursuing things where I get to make a substantial film about something that I care about or am inspired by, as opposed to just continuing to do more work that is the work to get by. 

I definitely have had moments, even in the last couple of months, where people are like, “You got to write a bio, and you got to tell us the things you’ve done.” I would love to fill in some blanks with more films before I comfortably say, “There’s a body of work there.” When I think of other filmmakers, like Brett Morgen, that’s a body of work. “Kurt Cobain: Montage of Heck,” the movie about Jane Goodall, the David Bowie movie, his “30 for 30,” I just see a person making one after the other, and they relate to each other. I feel like I’ve been cobbling stuff together—maybe, if I can get a couple more in, a pattern will emerge. But I’m not feeling that way today as we speak.

How confident are you that you can produce that body of work you want?

Everything is a labor of love you’re subsidizing or asking for favors. I exhausted my favor bank for “Flipside.” I’ve been having some conversations [with] friends of mine who are documentary filmmakers, and it’s pretty tricky out there. I’m trying to figure out, if you make something, who will see it? I have musician friends—they’ll have a new album and post something on Monday, but it will be forgotten by Thursday. There’s no middle anymore—it’s like you’re either making something enormous or something tiny. 

I’m confident I will continue making things because it’s a compulsion. I was doing a thing two days ago—again, no money, but it’s an idea. It was an instinct—it was a feeling—and I started to pursue it, and I started shooting. I flew to Las Vegas on my own dime to chase it. I just think I will keep following that instinct—the buzz of that, the feeling of that, the excitement of that still is real for me. But how to get things made and seen is a tricky question. 

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