Anna Kerrigan is a Los Angeles-based filmmaker with a background in independent film, digital storytelling, and theater. “Hot Seat,” which she wrote and directed, premiered at Sundance in 2017, as did her digital series, “The Chances.” She has written and directed short films for Funny Or Die, Amazon, and Refinery29, and is a Film Independent and Sundance Fellow.

“Cowboys” was scheduled to screen at the 2020 Tribeca Film Festival, which has been postponed due to the COVID-19 pandemic.

W&H: Describe the film for us in your own words.

AK: Set in Northwestern Montana, “Cowboys” is about a complicated father who tries to rescue his transgender son from his conservative mother by taking him to Canada. The film plays with Western tropes in a modern way. 

W&H: What drew you to this story?

AK: I used to visit my best friend’s family in this part of Montana as a kid and I’ve always been very emotionally attached to it. However, as I started to get older, I realized that a lot of the locals that I love so much are pretty damn conservative. I started writing “Cowboys” in a moment of upheaval and change in my life as a way of returning to a place I found comforting, but have mixed feelings about now as an adult.

The film is about two modern outlaws, a mentally ill dad and his transgender son. They are trying to escape persecution and find acceptance.

I love Westerns, but I’m really most interested in performance-driven films. While the movie plays with Western tropes, inspired by such films as “Butch Cassidy and the Sundance Kid” and “The Last Picture Show,” it’s really a character portrait of this family in crisis.

It was also important to me to make a film that portrays rural America sensitively, not as a monolithic swath of conservatism.

W&H: What do you want people to think about when they are leaving the theater?

AK: I want people across the political spectrum to relate to the father and son in the center of this movie regardless of their preconceptions. I think ultimately it’s a film about family, tolerance, and the trouble with being an outsider. Everyone feels like an outsider sometimes, so hopefully everyone will be able to relate to the two characters at the center.

W&H: What was the biggest challenge in making the film?

AK: There were so many challenges. We made this film with guns, kids, horses, and stunts for a very low budget considering what we accomplished. Every department should’ve had at least two more people in it. My amazing producer, Gigi Graff, literally drove around with a porta-potty attached to her truck at all times.

But I think the biggest challenge was finding a transgender child actor to play Joe. GLAAD consulted with us and my amazing casting director, Eyde Belasco, spearheaded a nationwide search. I think it’s tough enough to find a good child actor, and we further narrowed our scope by seeking out only transgender and non-binary kids.

It’s also such a delicate moment in any child’s life, especially if you’re exploring your gender identity. It’s a lot to ask a kid and their family to delve into those feelings for an audition for strangers when they’re undoubtedly so fresh. I met with a lot of kids and their families over Skype and was encouraged by how much they related to the script. And, sadly, how it paralleled the journey of a lot of kids — where one parent accepts the child’s identity and the other one does not.

Ultimately, we really lucked out when we found Sasha Knight who’s based just outside of Los Angeles. He’s very talented and understood the role. Plus, he looks like a little Paul Newman. He was already starting his journey as an actor so that was a huge plus for me. I feel like discovering a child actor — breaking someone in who’s never acted before, for example — can be dicier. You expose this kid and then they’re forever non-anonymous for the rest of their lives. 

W&H: How did you get your film funded? Share some insights into how you got the film made.

AK: The Montana Film Office gave us a Big Sky Grant to film in Montana, but the majority of our budget was financed by Limelight. I was at a screening at Sony of my short “Hot Seat” when this young woman named Natalie ran up to me and told me how much she loved the script for “Cowboys” a few years ago. I didn’t know this person and at the time, the film wasn’t set up — it wasn’t on any fancy lists and hadn’t been circulated or anything, so I was confused. It turned out she had been an assistant at United Talent Agency when she read the script. We hit it off — who doesn’t like to have their ego stroked by a stranger, I mean, come on — and stayed in touch.

A few months later, I heard from my agent that someone was interested in financing it, this guy Dylan Sellers. It turns out his daughter Natalie had sent him the script and it had also resonated with him. So, it really felt like a family affair. I think both Natalie and Dylan connected with the script because of the family element — the fact that it’s a story about a father and his kid. The Sellers all come from a line of producer’s: Dylan’s mom was also a producer back when it was pretty rare for women and Natalie is an exec at Annapurna.

I ended up giving Natalie an Associate Producer credit because if it wasn’t for her, we never would’ve met Dylan.

W&H: What inspired you to become a filmmaker?

AK: I really loved Miloš Forman’s “Amadeus” and all of Alfred Hitchcock’s films as a kid, but I always thought I’d be a writer. Being a director seemed like it was impossible for a little girl. My dad was a visual effects producer and he always said to me, “Don’t go into this industry unless you’re above the line.” I met lots of crew people through my dad, as well as some directors, but they were always dudes with ponytails and like a pierced ear.

When I was in high school, I interned for a USC film grad student and I was so obsessed with her that I ended up coming in for five days a week instead of the initial two. I was the production coordinator on her thesis film as a 16-year-old. Working on that film was the first time it actually occurred to me that there were female directors.

I studied theater at Stanford and then started in theater in New York, but I always wanted to do film, I just wasn’t sure how to break in. I was a PA on a bunch of things and finally I just started making these very DIY shorts and scrappy web series. As I self generated, I got better and better. But I have to say, I was desperate for a mentor and I really tried to entice people to mentor me, mostly men, and it was always disappointing.

Now I have a lot of people in my corner, but getting to this point has felt like a solo journey. 

W&H: What’s the best and worst advice you’ve received?

AK: I’ll tell you about the most discouraging advice that had the best outcome. When I was 21 and fresh out of college, I asked a man in the industry — who’d been like a second father to me — if he’d sit down and give me some advice. He asked me what I wanted to do and I said “I’d like to write and direct my own movies” and he laughed at me and said “Oh Anna, what makes you think anyone will want to watch your stories?” It was really horrible. And this was coming from someone who’d always been very nice to me. His advice was to get an internship and maybe be just a writer or just a producer eventually — now I’m all three. That meeting was like a knife through my vulnerable little heart, but it was important because I didn’t let it discourage me.

Being an artist is really hard and your work grows as you grow as a human being — so if some person, no matter how important they are to you, tells you you won’t succeed, it’s a test to see how dedicated you are in your heart to this path. For me, I knew, even though it made me feel like shit, that I was going to keep going, that in some ways, I didn’t really have a choice but to keep going. 

W&H: What advice do you have for other female directors?

AK: Being a woman gives you the opportunity to see the world differently than the status quo. Hollywood will try to pigeonhole you, but your unique perspective and your special insights extend beyond female stories.

Find other female directors, directors of color, LGBTQ directors and support them. Mentor younger voices and artists that need your help.

W&H: Name your favorite woman-directed film and why.

AK: “Toni Erdmann” by Maren Ade. It’s a three-hour heartfelt, direct, and honest comedy. I love the characters at the center of the film and I love how her comedy is derived from truthfulness and moments of the audience relating. It’s one of those movies that broke so many rules. It’s a great reminder that you can kind of do whatever you want as long as it’s interesting and surprising. 

W&H: How are you adjusting to life during the COVID-19 pandemic? Are you keeping creative, and if so, how?

AK: I’ve been writing, cooking a lot, trying to stay present, and letting myself be weird and feel all the feelings without self judgment.