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‘Cowboys’ Deals With Masculinity Issues With a Ton of Heart

March 3, 2021
4 min read time

Cowboys, Anna Kerrigan’s debut feature, is inspired by Butch Cassidy and the Sundance Kid, according to Kerrigan. The classic film is an indelible mark on cinematic history as well as a look at the archetype of the cowboy in general; with all the gunslinging, dynamite-exploding, Western-riding, criminal-activity-having action a movie can muster. The American cowboy image (especially if your father figure partially lives it) leaves a deep mark on a young kid, whether they are a boy, a girl, or still figuring that out. 

Cowboys asks its audience and its characters to reckon with how we present, value and expect certain things from the masculine, and what if all your young daughter wants is to become a cowboy. 

Filmmaker Kerrigan spent a lot of time in Montana and she says that’s where the first sparks of the story emerged.

“In my mind I kept seeing a father and son on a horse. I knew they were outlaws of some sort, and I began to piece together what if this father is a lovely dad who struggles with mental health and has a son who is trans.” 

Joe (Sasha Knight), who is at the center of this story as a kid longing for a cowboy life, starts the story with his dad on the run. At first glance it looks like these two guys are on a fun quest, but it’s soon revealed that Joe’s mom Sally (Jillian Bell) has not accepted Joe for Joe; she gives a police detective a photo of Joe as her daughter when he goes missing. Joe is kidnapped by his dad Troy (Steve Zahn), who felt he had to go to extreme measures to give Joe a fighting chance at the life he wants to live. 

Sasha Knight’s portrayal of Joe is courageous and not always an easy watch, particularly as Bell’s Sally grapples with Joe’s transition. Kerrigan stated finding her Joe was a search that succeeded thanks to well-known indie casting director Eyde Belasco.

“She’s so passionate about what she does,” Kerrigan said.

“We focused a lot on reaching out to grassroots [organizations] or nonprofits supporting trans youth or supporting their parents  from U.K. to Australia to here in the United States. We narrowed it down, worked with a handful of actors, we met their families and met them through Zoom," she said.

"Sasha was based in L.A. I was very charmed by him; I thought he looked like Paul Newman. Once cast, we spent a lot of time together. Sasha is trans and I didn’t want to be invasive of his own personal experience and how to bring it to the character  all actors we saw for the role were actually trans  but Sasha and I went through the script and discussed the scenes. Because Sasha is such a bright sunshine in real life, the only challenge was figuring out how to internalize Joe’s struggle.”

Sasha’s Joe owns the screen and his father Troy’s empathy with powerful lines like, “Sometimes I think aliens put me into this girl body as a joke.” Troy is instantly in step with and attuned to Joe’s pain and struggle, whereas Sally tells him, “You’ve got one body. You’ve got one path, and God’s got the game plan.” As Joe gets closer to Troy, the chasm between Sally and Joe grows wider. 

“It was important that Sally’s struggle was relatable,” emphasized Kerrigan.

“She is a woman who is very defined and constricted by her own gender  what it is to be a woman, and what it is to be a good mother. She’s very concerned how her family presents to the community. It feels abnormal to her. She’s so freaked out by what other people will think that she projects that onto her kid and wants to protect them from bullying but ends up bullying her own child, and failing to accept him for who he is.”

Kerrigan’s empathy for all her characters and her out-of-the-box casting brings both pathos and uniqueness to the project. Bell certainly felt like an unexpected choice for Sally, and Zahn shines in the role of Troy.

“In my experience, if you are able to do comedy you are likely to be very good at drama as well. I’ve always loved Steve Zahn. He’s really a gem of an actor, and I don’t feel like he’s been utilized as much as he can be. He’s so fun and charming and the dad everyone wants to have, and also has this other side where he’s really struggling,” Kerrigan said.

While Troy’s intentions are always good, they are often misguided; landing him and Joe in hot water time and again. It doesn’t mean Zahn’s Troy isn’t always a pleasure to watch  even when trying to shrug off his pain — as he gives his son a trip he won’t likely soon forget.

“The film is not only a coming-of-age story for Joe, but it’s a family coming-of-age story. A trans boy coming of age for Joe; he becomes a man by the end of the movie and there are a lot of mistakes that his father made, but I would hope that Joe as a young adult would be accepting of people and all their complexities," Kerrigan said.

"There’s no doubt Joe would have to go to some therapy after his journey, but because his family is open to acceptance, I think Joe will be, too.”

Kerrigan’s piece feels like the reinvention of a genre movie with revelations as frequent as dangerous turns for Troy and Joe on their epic Montana journey  a metaphor for transformation for Troy just as much as for Joe.

Cowboys is now available to stream on Amazon, iTunes, On Demand, and Redbox.

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