“More a Labor of Love Than a Paying Gig”: Chris Wilcha Returns to Documentary With ‘Flipside’

Chris Wilcha released his breakthrough film, the Slamdance award-winning documentary The Target Shoots First, in 2000. Like so many foundational Gen-X works—Douglas Coupland’s Generation X, for example, or movies like Reality Bites (1994)—it presumed that one of the worst things a twentysomething could do was “sell out.” In The Target Shoots First, this was examined through Wilcha’s vantage point working a day job at Columbia House, the infamous, then-omnipresent mail-order CD club that lured fans in with the initial promise of 8 CDs for a penny (followed by additional mandatory purchases at markup prices).

Wilcha had triumphed by turning his corporate job into art, but had trouble turning that art into a day job. After several aborted follow-ups, he turned to directing TV commercials, which gave him the income to raise a family. Flipside, which began as a documentary about the record store where he got his first job as a teenager, brilliantly repurposes several of his unfinished projects, much like an eclectic record store gathering rarities and B-sides, and makes them into something greater than the sum of its parts. (It also adds to them, as he revisits subjects like Deadwood creator David Milch, and New Jersey-based entertainer Uncle Floyd.) In a way, it’s a remix of Wilcha’s creative life, and in another, it’s a portrait of the privileged side of Gen-X in middle age, coming to terms with years of acquiring stuff and a marketplace that no longer supports much idealism, let alone free time to make art.

Released by Oscilloscope, Flipside opens in NY theaters today and in LA next week. In a conversation with Wilcha, edited for length and clarity, we discussed the ways he put it all together.

DOCUMENTARY: We’re around the same age, and I’ve always thought of my own inability to finish personal projects as a me problem. Watching your movie, I’m starting to think it’s a generational problem. 

CHRIS WILCHA: I think that I experienced it as a persistent me problem, and have carried this with me. When you’re doing documentaries, especially, that you’re trying to make a run at, you have to just start things unfunded because something’s going to change or a person’s not going to allow access. But it is challenging to sustain belief in things, especially when there are no resources to support it. One thing that drives me crazy about a lot of these projects is that they’re labors of love, and I can’t pay people, or I have to pay them some modest reduction of their normal rate, so I think that also contributes sometimes to the resistance to getting things done. As we’ve screened the movie, I have met and connected with a lot of people who have a lot of unfinished projects, and it would be a lovely outcome of the film if you saw it and it inspired you to follow through on the thing—be it the book, art project, or the movie.

D: Not many of us have had the luxury of holding on to all our old stuff, with moving and so on—how have you managed to retain all of these archives over the years? 

CW: It is an instinct that, as seen in Flipside, originates with my father, who I think has a similar instinct to save and archive and to make space in one’s life for stuff. It’s gotten a lot harder over the years to continue to do that. One benefit for me was that the ultimate storage facility was my parents’ house. They’ve lived in this house since 1980 or 1978 and I quietly request that they never open these two closet doors where stuff just accumulates and it’s temperature controlled. I turned 50 and it was time to return to the childhood closet and figure out what was in there—time to purge, maybe other things I wanted to keep—so that was a spirit of the film too.

D: Was there any point that you sat down and figured out the outline for the film as it exists in the current form, or was it always a process of improvising and discovery? 

CW: In this particular case, it was really in the making that the film revealed itself. I wrote treatments, I pitched the film, and I had a thought at one point that maybe it could be a limited series kind of format where you would do a David Milch episode or an Uncle Floyd episode. But I found that I was spending so much time pitching, or writing about what it might be, that I wasn’t making the thing. At a certain point, I just decided to try to do a standalone version of this film, like a single one-off documentary. I rallied a group of people that I previously worked with: an editor that I love and have worked with for many years, and a couple of producers, and we pooled our resources. This was mid-COVID when everyone was looking for ways to keep working and exercising our brains, and it was the benefit of that weird lull that allowed these very talented people to stop for a moment and focus their attention on something that was more a labor of love than a paying gig. So that helped.

D: So was the stand-alone just going to be about Flipside records, and then you pulled all this other stuff into it?

CW: Early on, I didn’t think that an entire film could be made out of the record store. I think that I knew that, but I still felt like it was a really compelling portal into my past and reflecting on ideas about accumulating things, purging things, and the magic of analog treasure hunting. The bet I was trying to place was I found a lot of this old footage on hard drives, and I was like, this still feels like there’s meaning in this footage, there’s energy in this footage. Can we combine these things, can we have characters recur, can we weave this together in a way into a weird essay? That could only be tested by actually trying it out, and that was the gift of the editors that I worked with. Claire Ave’Lallemant and Joe Beshenkovsky put in the time with me to prop it up and there were a thousand versions of it, including versions where everything was completely standalone.

There was a breakthrough moment where we realized, oh, the voices could recur, like [the late jazz photographer] Herman Leonard could be at the beginning, and then we could reprise him, and he could help amplify the meaning of a different section. There was no way to outline this one into existence; there was no way to write a treatment that was going to figure it all out on paper. When footage started getting put up against other footage, and we started trying to weave together the different stories, that was when things started to get exciting and make sense.

D: We’re from the pop culture that came of age in the time of hip-hop sampling, club music, and repurposing of old things to create something new. Did you feel that kind of mindset when you were putting this together?

CW: I don’t know that there was a direct thought, but I think I’m completely of that moment in time of using stuff from the past to try to make something new. Digitizing all of this stuff all of this footage made it a lot more manageable to look at. When I digitized my Hi-8 collection it was kind of a revelation. I’d just been accumulating footage for years and years on these cassettes. and you have almost no occasion to sit in real time and look at a cassette and scroll through it. But when you digitize it and it becomes a Quicktime and you can scrub it, and see, “Oh my God, I have this footage of a moment in New York City, or this building that was knocked down a month later, this concert that I went to!” It made me discover what was in that accidental archive a lot more quickly, and that was a total gift. In its analog form, it would have been an unmanageable real-time activity.

D: Assuming this movie does well, are you going to go right back to commercials after this or do you see a way to finally realize the filmmaker dream?

CW: Based on the marketplace right now, it’s tough. This is a weird moment; a lot of the streamers’ budgets around documentaries have contracted and their acquisition of documentaries has shrunk. The algorithm is rewarding certain kinds of massive-spectacle documentaries that are either celebrity-based or true crime, so I am not taking my commercial directing gig for granted. It’s probably always going to be some kind of balance between the two. The hope is to work on and continue to make documentaries, but I don’t have any delusions that anyone’s necessarily going to pay me to do that.

D: What about doing something like Catfish (2012) or Morgan Spurlock’s 30 Days (2005–2008)—a TV series where you go and help people realize their unfinished projects?

CW: Hey, listen, if you wanna help me pitch that...If other quote-unquote IP could come of Flipside, that would be amazing, right? I feel like there’s a scripted film in there too, like a midlife crisis gone awry. There are stories still to tell around Flipside and this moment in time.

D: When you were making this, could you even allow yourself to think this might be a generational thing?

CW: It would probably be a little grandiose to say that I ever thought of it as a generational thing, although I did have a lot of friends who related to it and I thought that that was a good sign. The dream is, you make something, and the hope is you like it and that others will be interested in it, but I was also conscious of, like, does the world need the story of “a middle-aged white guy reflecting on his life”? The answer’s probably no, but I wanted to make it, and what’s been nice is that I think people are connecting with it in ways that I didn’t expect. 

D: Do you just want to make documentaries, or would you want to do a fiction version of this film or a completely different fiction film?

CW: It’s funny, because even in the commercial world, I’m casting actors, it’s all made up, it’s rarely documentary even if it’s in the documentary style. But for some reason, I’ve often had meetings where someone will say “We love your stuff, but we aren’t gonna be the first people to take a chance on you in this space,” like working with known actors or something like that. I love nonfiction, but I love all forms of filmmaking, and it would certainly be a cool thing to have that opportunity. You know, I think that for the moment I’m still kind of pursuing documentary-based ideas.

Luke Y. Thompson has been a professional entertainment writer, film critic, and editor since 1999, starting at New Times LA, with bylines in the LA Weekly, LA Times, Nerdist, Deadline, Village Voice, Coming Soon, and many more. He has also appeared as a talking head in the documentaries Unknown Dimension: The Story of Paranormal Activity and Fuck You All: The Uwe Boll Story. Follow him on most social media sites @lytrules.