Interview: Filmmaker Anna Kerrigan Talks ‘Cowboys’

Having won awards from festivals like Tribeca and Outfest, it’s clear that Cowboys is a movie that has been resonating greatly with those who see it. A tender story about a family in the Montana wilderness, writer/director Anna Kerrigan takes a look at how our different experiences and struggles can shape our perspectives and the ways that we respond to those around us. 

Starring Steve Zahn and Sasha Knight as a father and transgender son who go on the run, with Jillian Bell as the boy’s distraught mother and Ann Dowd as the detective on their trail, Kerrigan crafts a character piece that evokes old Westerns just as much as it does classic movies about parent/child relationships, like Paper Moon and You Can Count on Me. 

I got the chance to speak with Kerrigan about the film, where she told me about what inspired this story that she describes as a “coming of age as a kid and a coming of age as a family”. It was an in-depth conversation, where we not only spoke about the childhood of this character and his struggle in the world, but even got into our own childhoods, and how those experiences inform the ways that we look back on our past, while also shaping the worldview that we have today. 

Check out our review of Cowboys here, and see my conversation with writer/director Anna Kerrigan below: 

I wanted to start by talking about how this story came to you. I had read that you spent some time in your youth in the Flathead Valley in Montana. Was returning to that environment as a filmmaker something that you always wanted to do, or was there something about this particular moment in your life that prompted that desire? 

Anna Kerrigan: It was the latter. I used to go to this part of Montana with my best friend’s family for a few weeks every summer, starting around when I was 10. I was super obsessed with that part of America, and then as I became a teenager I started talking about more complex social issues and realizing that the people there had very different perspectives than me. I think that’s always something that I’ve felt very conflicted about internally with some of these folks in Montana, although certainly not all. I was moving back to Los Angeles after living in New York for ten years, and I felt very unsettled and nostalgic for a place of security, so I started writing this script that took place in Montana. 

At first I was very bewildered by what I was writing, because it started with a father and son on horseback, and I had never written anything that was in the wilderness, or even about a father and son. All I knew was that they were outlaws, and I sort of gradually discovered through writing that they were outlaws because the dad is dealing with mental health issues and the son, who is like his soulmate, is transgender, and they’re in this community, and in this household, that doesn’t quite accept or get them. 

Did you draw from your own life when creating these characters? 

The most personal part of the script for me was the family dynamic. I think as a kid I had sort of a blurry relationship with my parents, in that there was always some question of who was the adult in the relationship. While my parents were very loving and well intentioned, they’re similar to Troy and Sally, Steve and Jillian’s characters, in that they’re all trying their best, but we can only do as well as we can with the tools that we’re given. 

The aesthetic of the movie calls to mind Westerns like Butch Cassidy and the Sundance Kid, while that idea of who is the parent and who is the child speaks to elements of the movie feeling drawn from something like Paper Moon and the character dynamics there. What were some of your influences while making the movie? 

Well, you just named two of them! Butch Cassidy was definitely one, and Paper Moon was never one that came to mind specifically for whatever reason, but is definitely there. I love The Last Picture Show. I’m trying to think back on the look book that I had where I listed all of these things that were elements that I thought about while making it. Billy Elliot, which is a totally different movie, but has similar ideas of a kid that was different in a working class family, and he’s trying to negotiate that with his parents. Also Fargo, while being tonally a completely different movie, was something that I had in mind just in how the Coen brothers integrate place into their films. You Can Count on Me is another one. 

This movie does draw to mind that feeling that you get from Bogdanovich’s films where it conjures a kind of nostalgia while mixing it with these darker parts of being a kid that you sometimes don’t think about when you’re looking back. 

Yeah, I remember even in my childhood being depressed because I kept feeling like this isn’t the rosy childhood I’m supposed to be having. I think it’s really hard being a kid, you pick up on so much more than your parents give you credit for. Kids are amazing liars, not in the sense that they’re concocting lies, but that they’re performing as if things are okay. Kids are so adaptable, they really work with whatever they’re given. You’re really trying to accommodate, and be the kid that works for what your parents want you to be. As an adult it’s funny to think back, like oftentimes the “problem kid” is the one most in tune because they’re the ones that are likely reacting to something that’s real. 

The kids who are more vocal about what’s going on with them emotionally are the ones who aren’t holding it in. 

Yeah, totally, like this is getting very personal, but looking back as a kid I had a stomach ache for like four years. I always thought that I had this mysterious illness, but now I reflect on it, and I realize that it was actually that I was really stressed out and upset all of the time. 

I can relate very strongly to that. I had a stomach ache every day of school practically, and my mom always thought I was faking it, but I was like, “No, my stomach really hurts”. 

Oh yeah, what sensitive little creatures we were. We still are. (laughing) I didn’t know that we were going to be talking like this! 

Speaking of childhood, Sasha Knight delivers an amazing performance in the film, which is also his first time on screen. This is such a big role for a young actor to take on, and you were adamant about needing to cast a trans actor for this part. Could you speak a little about why that was such an important aspect of casting for this character. 

I wasn’t confident that a cisgendered kid would get the role, and I really needed someone who could bring their own experience, and understand what the character Joe was going through. We did a very epic search. My casting director and I went through the normal channels first, and then we also got the word out through grassroots organizations, and summer camps, and all sorts of social media accounts just trying to find these kids. It’s such a delicate age, and we needed someone young enough that the character would buy into his dad’s fantasy that they’re going to go on this journey. We narrowed it down from like 50-60 people down to 12, and then I worked with those kids, and met their families over Zoom, and we narrowed it down further. I was so relieved when I saw Sasha’s first tape because it was so obvious that he was the kid. I met with him in person, and we spent a lot of time before shooting doing journaling exercises, and going through the script together. I just wanted him to be as comfortable as he could be, but honestly as soon as he got on the set he was so excited. It was just like the best thing that had ever happened to him. 

It’s a pretty big deal for your first part to be the lead in a movie, and you’re working with people like Steve Zahn, Jillian Bell, and Ann Dowd. 

Sasha knew them too! Well, he at least knew of them. He was a fan of Steve’s, I think he had seen him in Diary of a Wimpy Kid. The two of them became really close, and still are. 

That’s definitely something that comes through in their relationship in the film. It’s hard to fake a bond like that on screen, especially when one of the actors is a kid who doesn’t have a lot of experience yet. Both Steve and Jillian Bell are actors who have done strong dramatic work before, but are mostly known for their comedic roles. Was that an intentional choice to cast actors known more for comedy in these parts? 

I looked at actors that were known for all sorts of things. The tricky thing is that actors get pigeonholed so often, and I think especially if you’re good at comedy, which I think is so much harder to be good at, then you can be locked into that. With Steve I needed someone who could feel like an underdog. If you put Tom Cruise in that role, it’s like you can’t separate Tom Cruise from doing Mission: Impossible, and the part wouldn’t be able to resonate in the same way. I needed someone for that part who could be super charismatic and so fun. Steve is a charmer, but then you also have the character’s mental health issues which manifest in a way very specific to him. I had seen Steve in Rescue Dawn, for instance, but even in some of his comedic roles he mines dark stuff in a fearless way. I knew that I needed all of those things, to have someone super dynamic. 

Jillian and I have the same agent. She had read the script, and we met for dinner or drinks or something, and we had this really long conversation about the role, and she just understood her. I had been a fan of Idiotsitter, and she is such a smart person, and was so excited to take on the role. I was confident that she would be able to ace it. 

Jillian’s character is the hardest one to reckon with in the movie, because she’s the one who puts up the resistance to everything, particularly Joe’s gender identity. A lot of the time you’d see a character like this be villainized as a one-dimensional monster, but you find ways to allow the audience to understand how her view of the world has been borne out of where she grew up, and what she’s been surrounded by. There’s one scene in particular where she’s arguing with Steve’s character and says, “I wouldn’t choose to be a woman either!”, which speaks to her internalized transphobia, as well as her perception of gender roles that’s been ingrained in her. Could you talk about the importance of making your characters well-rounded, and bringing this dimensionality to them? 

I always try to do that. No one sees themselves as the villain, and I think that even if a person’s belief system doesn’t line up with yours at all you have to understand why they are the way that they are. I think something that’s interesting about her character Sally, and can be universally applied to a lot of people, is that her insecurity and her internalized idea of how other people view her and her family is really what gets in the way of her loving her child. She’s someone who is super locked into her own gender, and this idea of what a woman is, what a mother is. She is sort of willingly subscribed to this prison, and that was really interesting to me, as by the end of the movie she is also liberated from these shackles that she put on herself. 

Performing gender is an interesting idea that comes up in this movie. As a nonbinary person myself, a scene that really stood out to me was the one in which Joe comes out to his father. When Joe first explains that he’s a boy, Troy responds by thinking that he’s just saying he’s a tomboy because he doesn’t like things that have been gendered as being “for girls”, like dresses and dolls. Joe resists that label though, and puts his foot down and states that he is a boy, not a tomboy. Why was it important for the character to make that distinction known? 

I am cisgender, so these are things that I’ve had to discuss at length to try and make sure I’m getting right, but it’s like your gender is not your choice, it’s who you are. It’s something that only you know, and it’s been really interesting with this film how even among liberal people there’s been a lot of confusion about what gender is. I’ve had a lot of discussions with people that have shocked me because they question how you would know at such a young age, and I ask them how you wouldn’t know. Like, how does anyone know that they’re a girl or that they’re a boy, or whatever their identity may be. I think it’s triggering to some people because I think for most people who identify as the gender they were assigned at birth they don’t question the fact that society is doubling down on how they present their gender. If it isn’t challenging who you are inside then you don’t think about the fact that you’re getting tutus and tiaras, or you’re getting trucks and G.I. Joes. Gender is a really tricky thing, and even if you do identify as the gender you were assigned at birth there’s a lot to buck up against. I think that’s really triggered people in causing them to think about their own gender, and questioning the things that they’re buying into that they’ve never even thought about. 

Speaking of gender, I wanted to talk about the casting of Ann Dowd as the detective charged with tracking the boys down. This is another instance where it isn’t the kind of person you’d normally expect to see in a role like this. Often you’d imagine the part being cast with a gruff, older veteran male actor, like Tommy Lee Jones or Jeff Bridges. Dowd has been working in the industry for decades, but has recently been seen in more villainous parts, like The Handmaid’s Tale or Hereditary. When you first see her you get this idea of how we’re supposed to feel about her, but she ends up having a gentleness to her that is a bit surprising, and we understand that she’s genuinely looking out for everyone’s best interest. What drew you to her for the part? 

Well, I love Ann so much as a human being, just as a sidebar. She’s so amazing, and I want to work with her again so badly. The gross Hollywood answer is that she has the same manager as Steve. I had already cast Steve, and I was looking for casting Ann’s part and so their manager suggested her and I knew right away that she was perfect. This character is a veteran, she’s been doing this for a long time, and is kind of on her way out, like this is one of her last cases. Unfortunately, there aren’t a lot of women her age in Hollywood who look real in the way Ann does, and she has this humanity to her even in her darker roles that I thought would be a great counterpoint to this sort of character. She has this funny perspective where she comes in and sees the difficulties the family is struggling with, and is just like, “I don’t care what you guys are dealing with. There’s a missing child, and we just need to find this kid, and all of this other stuff is just shenanigans.” 

That reminds me of the scene in The Fugitive where Harrison Ford says, “I didn’t kill my wife”, and Tommy Lee Jones responds, “I don’t care”. Like it’s not her job to get into any of this other stuff. You also mine some great dry humor out of Ann Dowd, and there are other areas of the movie where you find these pockets of levity to counteract some of the heavier themes being dealt with. Was it important for you to make the movie emotionally well-rounded? 

Yeah, there are two things that were important to me. One, that this movie didn’t feel like an “issues movie”. Ultimately, it’s about a coming of age as a kid, and a coming of age as a family. Often movies dealing with these kinds of themes can feel really heavy and miserable, and I just don’t think that’s true to the human experience. I think when you have a more well-rounded movie, where there is levity and humor, it makes a balance, and that also makes the darker moments land even harder. The other thing I thought about a lot is that I think there’s a fetishism that happens with movies taking place in rural communities, where there’s this idea that if you’re working class then your life must be miserable all the time. The reality is that when people are going through it there’s always humor, and there’s always lightness, and that’s just life. I don’t want to work on a movie where I’m slaving away at an edit, and there’s never an opportunity to laugh. 

Cowboys releases in theaters and on VOD on February 12th, 2021.