I like that idea that when you’re in nature you can be your true self, and not influenced by the constructs of your society. It’s a really interesting way to re-appropriate nature, sort of nodding to a genre which is so heteronormative and so male as some sort of backdrop. I have to admit I was not consciously thinking about all of that when I put the film together. The movie came to me very organically. 

Anna Kerrigan

Growing up in the Chicago suburbs, my mother would always talk about this place called Montana. The way she would talk about it made it seem like a piece of heaven, or what heaven might look like if I believed in such a place. When I was 15, I went to Montana with my family, and then I got it. Glacier National Park, specifically, is so beautiful that it almost hurts. The streams, waterfalls, the mountains, the trees, the air, the wildlife, it truly is heavenly.

Anna Kerrigan

When I spoke with Anna Kerrigan about her film “Cowboys”, she agreed with me. Growing up she would travel to Montana with her best friend’s family. To Anna, Montana was another home. As an adult, a liberal creative, with many LGBTQ friends, it was difficult for her to reconcile her love for a place and people who were so against the LGBTQ community. That conflict sparked her film “Cowboys”. The film is about a trans boy, named Joe, played by trans actor, Sasha Knight, and father, Troy [Steve Zahn], who suffers from mental illness. Both father and son leave the judgemental constructs of their society on an adventure into the wilds of Montana heading towards Canada. Also starring in the film is Jillian Bell as Sally, Joe’s mother, and Ann Dowd as Faith, the police chief looking for Joe.

Anna and I discuss the road to making “Cowboys”, her casting choices, and the process of casting a trans actor in the role of a trans kid. “Cowboys” is currently on the festival circuit, and was supposed to premiere at Tribeca last month. The film is now seeking distribution.

REBECCA MARTIN: What brought you to this project?

ANNA KERRIGAN: Growing up, I had spent my summers in Montana with my best friend’s family. I just fell in love with it. I grew up in LA, and I was pretty much a city girl. Montana, to me, was kind of like this American fantasy. It was so beautiful. I thought the people were so nice, and the towns were so quaint. It satisfied this itch that I didn’t even know I had when I was younger.

MARTIN: I can relate. I grew up in the Chicago suburbs, but we would go to Montana every couple years. It’s really a different world.

“Cowboys” DP John Wakayama Carey

KERRIGAN: Even going back and making this movie, it feels like the edge of the world. I know that it’s a state, but sometimes it feels more like a territory. It’s just it’s own thing.

As I started to get older, I was a creative, very liberal kid, and I always had a different group of friends. And I realized the people I befriended in Montana were really religious and would make super-homophobic comments. It was confusing to me because I knew I loved the people there, yet I’m a super liberal person who has a lot of LGBTQ friends. How do I reconcile those things? I think that conflict was the seed for this movie, although I would say it was subconscious when I first started writing.

I lived in New York for a long time, where I started out as a playwright. When I moved back to LA, it was a period of transition, and I was in kind of a dark place. I knew I wanted to set something in this part of Montana where I would visit, because I found it was comforting. Even though I was home, I always homesick for Montana. When I first started writing, all I really knew was that it was a father/son movie, and as it started to develop, it became clear that the son would be trans.

I don’t think of this film as a western. I’m much more interested in performance-driven films through the characters. I think that comes from my playwriting background. But I like to say there is a western shell on the movie with illusions to “Butch Cassidy and the Sundance Kid”. I will always love “The Last Picture Show,” which similarly is a good character portrait.

MARTIN: Yes, I love that film. 

Sasha Knight and Steve Zahn in “Cowboys” DP John Wakayama Carey

KERRIGAN: But in terms of who are the new outlaws, who are the people being persecuted in these type of places–of course, in these environments it’s the transgender son and a mentally ill father. And they feel like they have to get away.

MARTIN: I love that you captured that. How did you go about the casting process?

KERRIGAN: First we started with the adults, and Troy first. Steve [Zahn] was on our list, and the more that we thought about it, we realized that he is really perfect for this role. We haven’t really seen him in a leading man role. He’s a fantastic actor. I also thought it was important to the movie that you had the feeling that this guy was an underdog. And I do believe that actors come with their own baggage. If you put Matthew McConaughey in a role like that, you’re never really going to see him that way.

MARTIN: I see that.

KERRIGAN: He has that sort of larger than life energy to him. I wanted him to be someone who could fall into the deeply flawed, but super-fun Dad. I mean there is a child-like quality to him, like a playfulness. I remember seeing Steve in Wim Wenders’ movie “Rescue Dawn”, and you can see that he can go there, he can go to dark places, and he just hasn’t been given the opportunity. I was really excited about him. He really responded to the script, and afterward, when I spoke to him on the phone about it, he was like, “I’m so sorry if it’s loud”. I told him I didn’t know what he was talking about. He said, “I’m just feeding the animals.” I find out he lives on this farm in Kentucky. 

MARTIN: Really? That’s interesting. 

KERRIGAN: Yeah, he’s been out there for awhile. He understands the conflict of being a liberal guy living in a red state. He’s raised his kids in this small town, and he is the minority with his liberal beliefs. But he also can connect with people who do not share his political views.

Steve Zahn and Jillian Bell in “Cowboys” DP John Wakayama Carey

MARTIN: What about Jillian Bell? How did you go about choosing her for this role as Sally? I’ve never seen her in this kind of role before. She usually is the comic relief in films, and seeing her in a more dynamic, serious role really showed her range as an actor.

KERRIGAN: It’s funny, I had a meeting with Jillian and she really responded to the role. I was suddenly meeting her and talking with her, and seeing how much depth she has as a human being. And I saw that she was really interesting as this character. That being said, Sally is nothing like Jillian. Jillian is the kindest person who is full of heart, and I know it was hard for her at times. I think this happens to a lot of actors. If you’re going there emotionally, it can be really taxing to put yourself in this position of being a fairly toxic person in this moment of crisis. Jillian is incredibly smart and has great instincts. She really understood the role. It was important to me and it was important to Jillian as well to not see Sally as the villain. 

MARTIN: Definitely not, she represents a lot of people. 

KERRIGAN: The character Sally feels that she doing the right thing based on the limited tools that she has. And for her, her daughter coming out as a boy is shattering her self-conception as a mother to a little girl. She literally just can’t comprehend it. In some ways, I find that Sally’s character finds herself in the prism of her own gender. She tries to perform this ultra feminized idea of being a woman who’s a mother, who’s a wife, and it feels like a personal failure to her. She feels like a failure because it’s not working in the way she imagined. 

Ann Dowd in “Cowboys” DP John Wakayama Carey

MARTIN: I was very impressed with Ann Dowd as Faith. She is great in “The Handmaid’s Tale” and I think it’s great that you brought her in for a different kind of role. It seemed perfect for her character. 

KERRIGAN: She is such an incredible actor, and is so thoughtful. Ann is so intuitive and picks up on everything. I loved working with her because she challenges me in the most generous way an actor can. She was always working towards the good of the project, and always asked really brilliant questions. Ann is the most emotionally supportive, amazing person. I always tell her that she is my queen. She brought so much depth to the character, as she has done in all of the roles I’ve seen her in.

MARTIN: In your director’s statement, I read that “I Am Jazz” was an influence on your choice of bringing on a trans actor for the character Joe.

KERRIGAN: I only brought the show up in the Director’s statement because when I was setting out on making a portrait on this part of the world, what I found interesting was the people that I have met in rural Montana and in red states, and their reaction to the series. I found that programming like “I Am Jazz” introduces people to transgender kids, and does change their mind, and their conceptions. It plays on the idea of the power of media and compelling characters.

There’s a woman who I met in Montana who I’ve been friends with since I was twelve years old, who voted for Trump, and has some conservative leaning views. When I told her that I was making a movie about this trans kid in Montana, she was super-excited. She was like, “Oh, I love ‘I Am Jazz,’ that kid is so cute.” She was using the correct gender pronouns, and I thought that was really interesting.

MARTIN: I loved the construction of the film, with the two story lines weaving together, the past and the present. Can you discuss your process of intertwining these storylines?

KERRIGAN: The script was such a mess because I didn’t really outline. I knew a couple of the pivotal moments, but this is an instance where I really just went for it. I probably wrote 300 pages at some point, and basically printed it out scene by scene so I could figure out how to structure this story, going back and forth from the present to the flashbacks. I hate to call them flashbacks because it’s such a meaty part of the film. The story I was telling is non-consecutive.

It was too confusing. So we found a way to make it work where you are basically following two storylines, with the past and the present in the first two thirds of the film, and then it clicks in to where it all gels together. 

MARTIN: I really appreciate how more is revealed that way, when the past connects to the present. I was sucked into both storylines. When we start to see Troy and Joe unravel, we have a better understanding of why it’s happening, based on the vulnerabilities and struggles that were introduced to us from their past.

KERRIGAN: When we looked for locations, I tried to find places that progressively became more and more terrifying. By the time they [Troy and Joe] get to the dead forest, they are exposed. It’s no longer lush and beautiful. There’s no longer that potential that you feel when they are looking out over the vista in the beginning.

MARTIN: Let’s loop back, can you please share how it went in casting a trans kid?

Sasha Knight

KERRIGAN: I started talking with Nick Adams, who is a transgender media relations person at GLAAD. He was helpful in terms of various script notes and what not. I also worked with casting director Eyde Belasco who cast “Transparent” along with a million other projects. I worked with Eyde before and thought she’d be perfect for casting the film. It was really important for us to cast a non-binary and trans kid, which is inherently tricky because it’s hard enough to find a kid and even harder when you are narrowing the scope. We looked at kids who had never acted before, but of course, unlike a cisgender child, their sense of personal connection to the character far outweighs their experience as an actor. Eyde went through the normal channels of various breakdown services, and also did outreach through transgender support groups, summer camps, and connecting to parents of transgender kids.

From there, I would talk to a handful of kids and worked with most of them remotely because a lot of them weren’t in LA. It was an amazing experience and was really encouraging to me as a cisgender woman seeing transgender kids read my script with their parents. They were relating to the script, and finding it resonant. The parents were finding parallels to their lives, very unhappy parallels. Unfortunately there were a number of kids that I spoke to who had a difficult relationship with their parents or were estranged from them. Eventually we found Sasha [Knight], and it was pretty clear immediately that Sasha was great for the part.

MARTIN: Yeah, he’s great.

KERRIGAN: Yeah, he’s awesome. I just felt like he understood the character. He’s smart, and honestly a very adorable child. I just thought that his intelligence and introspection was far beyond his years.

MARTIN: Based on your experience as a filmmaker, do you have any advice for emerging female filmmakers?

KERRIGAN: Even as women are directing more, there is still a pigeonholing going on. Like women being put up to directing teen girl’s stories. There’s nothing wrong with that, I did a teen girl short that I love. But even being chosen to direct female centric stories is a form of pigeonholing. I would just say as women you see more of the world. You have a unique perspective. I would just tell women not to hold back when telling stories, and not just about women, although I do think women’s stories are incredibly important. I think our observations about men are just as important. 


  1. Karen B Massaro

    Where can I find this movie? I have a Trans son and would love to see this.
    Finally a movie about a Transboy!

  2. Pingback: The 50 best films of 2021: Part 1 (50 – 26) – Cinema Femme

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