Gill Holland has a way of saying things that makes a 30-year career sound like a happy accident. Mention that he might have more film credits than anyone else in Kentucky and he shrugs it off. “I’ve been working on movies for almost 30 years,” he says. “If you work on like five films a year for 30 years, you somehow get to 150. It just kind of happens.”
That shrug hides a life spent in the trenches of independent film, where “it just kind of happens” usually means endless rejection, maxed-out credit cards, and the faint hope that someone, somewhere, will eventually watch the thing you nearly broke yourself making.
In Louisville, Holland is known as a developer, a civic booster, a guy tied to NuLu and Appalachian projects. “In New York City, nobody knows I do stuff like NuLu and Harlan County. I’m only seen as a film producer.” And producer, in his telling, is less a job title than a long-term condition: “You’re the first person on a project and the last person. I’m still working on films that were made 20 years ago, still trying to monetize them and get them out in the world.”
That includes documentaries like Flow: For Love of Water, which premiered at Sundance in 2005 and just keeps getting more relevant. “Every week there’s another email from somewhere. Somebody wants to see Flow,” Holland says. “Post-Flint, Michigan, it’s only gotten more relevant.”
Then there’s the Big Star: Nothing Can Hurt Me documentary, a film that feels like required viewing if you’ve ever loved a jangly guitar band that never quite got its due. Holland traces that one back to timing. “We were at South by Southwest the week Alex Chilton died,” he says. “We were like, ‘Oh my gosh, we’ve got to put together a tribute band.’ And then I was like, ‘We need to film this. We need to make a documentary about Alex Chilton.’”
It took five years to become a finished film. Some of the original footage never even made it in. That’s the pattern. “You don’t realize how hard it is,” Holland says. “I’ve had so many films rejected from Sundance since then. I’ve been lucky to have like 14 films that have played there.”
Rejection, he says, isn’t a phase. It’s the job. “You want an actor — they reject. You want an investor — they reject. You want a location — they reject. You apply to Sundance — they reject. You want Netflix to buy your film — they reject.” He laughs, because what else do you do? “You have to have thick skin.”
Holland came up during the ’90s indie boom, when it briefly felt like the walls around Hollywood had cracks in them. He traces it back to John Cassavetes, then forward through Richard Linklater, Jim Jarmusch, and the idea that you could work outside the studio system and still matter. “We were like, we can work dependently on all our friends,” he says. “Everybody can share in the profit if the film is successful. We can disrupt creative accounting.”
Digital video kicked the doors even wider. “Before, to get access to a 35mm camera, you either had to be rich or go to an amazing film school,” he says. “With digital video, the floodgates open. Now filmmaking is just an art form. You can literally make a feature film on your cell phone.”
If that all sounds optimistic, Holland knows better than to romanticize the present. Distribution is the buzzkill. Netflix doesn’t need your indie anymore. Amazon is pickier. Everything feels like it costs less and matters less at the same time. Still, he thinks the pendulum might swing back. “With AI, all these Marvel films are going to be made by four English majors who are really good at writing prompts,” he says. “But indie film? We don’t even use CGI. Actors, theater, live performance — chatbots can’t do those things.”
His own start was pure indie mythology. His first feature, Hurricane Streets, was essentially self-financed. “We literally put all our credit cards on a table,” he says. “We were like, we can shoot in our apartments. In New York City, you can shoot for free on the streets.” The film went to Sundance, won three prizes, and sold to MGM. “Life has been downhill ever since,” Holland jokes.
From there came documentaries like Dear Jesse, narrative films like Sweetland — rejected by Sundance, then winning an Independent Spirit Award anyway — and cult detours like Greg the Bunny. That one started as a scrappy puppet show by a group of NYU friends. “I was like, ‘Oh my god, this is so good,’” Holland says. It ended up on IFC, then Fox, with Eugene Levy and Sarah Silverman. “IFC was funnier,” he admits. “We had more creative license to be disrespectful.”
Silverman is back in Holland’s orbit now, starring in a new drama shot in Louisville. Bonnie “Prince” Billy keeps popping up too. “I want to put my friend Will in every movie that we do,” Holland says. Lately, he’s also been shooting in eastern Kentucky, trying to tell Appalachian stories that don’t feel like stereotypes. “Hollywood has often told the negative version,” he says. “We have amazing stories here.”
Which brings it back to Louisville, the city he never planned to champion this hard. “I joke that I was auditioning cities,” he says, post-New York. What he found was a place where creatives could live without burning out. “Here, you can support yourself without working 80 hours a week,” he says. “Buildings are like movies. You find a property, you hire a director — an architect — you assemble a crew, you tell a story. And I like telling stories.”
150 films later and stories that continue to find new champions.
Listen to the full interview above and check out the trailer for Unknown Country below.
