Anna Cain: Writer, Actress, Comedian, and Veteran

Stowe alum Anna Cain Discusses her service and how it intertwined with her writing

By Marian Cook

Anna Cain

The beauty of the filmmaking community is the breadth of diverse backgrounds. At Stowe Story Labs, that’s something we take to heart: regardless of background, anyone with a terrific story and the drive to do the work and collaborate should be empowered to push the work forward. In our community, we have any type of person, from bakers to scientists, dancers to nurses, and also veterans. Anna Cain is one.

Anna is a writer, actress, comedian, alum of the 2018 Stowe Writers’ Retreat, and an Army veteran. She served 5 years working on encrypted radios, was a communications sergeant on convoys, and did a tour of Iraq in 2006.

Aside from her many kick-ass abilities—like being trained in MAC (Modern Army Combatives) levels 1-3, firearms, kickboxing, boxing, and “taking a slap like a champ”—her time in the Army influenced her writing, too.

“It made me a lot more focused, especially when I first got out because when I started my undergrad, I was 24. And a lot of the things that seemed to stress everybody else out, I just was like, ‘Yeah, that's not a big deal,’” Anna explained.

It also helped her develop a darker sense of humor. Blithely, she recounts a story about her and her fellow soldiers choking each other out to get a rapid rush of sleep and her non-military friends being disturbed by it. But Anna makes a good point: we don’t know what we don’t know.

“As I've gotten older, I’ve stopped trying to color everything nicely for everyone and realize that when I'm doing my writing, it's okay for me to make jokes, make comments, make characters that might make people uncomfortable, as long as there was a point to it,” Anna said. She’s begun exploring darker themes and is even starting to pull away from only comedy—her first love.

Since she was eight years old, Anna has been dabbling in comedy, satire, and horror. Her “it clicked” moment was the Matt Foley sketch on SNL with Chris Farley because it was something that she used to replay for her mom to make her laugh.

Anna recounts, “I would sit in my room and I would write little sketches like I was a writer on SNL and then just act them out in my room by myself, have conversations with cast members because I’m a weirdo, but out loud. So my mom would come in like, ‘What are you doing?’ Like don’t worry about it, I’m manifesting!”

Currently, she is working towards her MFA at Sarah Lawrence College, and when she’s not studying, you can find her doing film and TV projects around NYC—in fact, she just got cast in an indie horror comedy that's going to start filming later this year.

But there was a point where she did stop writing, despite it being her safe space. “I started trying to write a story about one of my best friends who died while I was [in the Army], and I never finished the story. I couldn't. And then after not being able to finish that story, I really did stop for a while. I wouldn't write about any sort of military experience, honestly, up until this past year. I refused. When I was doing stand up, I wasn't making jokes. I did mild jokes about my service, but I wasn't going to talk about anything that was real or that came from a traumatic space because I just don't think I was ready to do it.”

Some of the toughest aspects of her return home were the negative reactions she would get when she told people she was a veteran; the morbidly invasive questions she would get about her service, and gross assumptions about why she joined; and relating experiences that civilians will truly never understand.

“It's taken a long time to get to the place where I am right now, working on a story for my workshop class. It’s the first story that I’ve written about military service and it's therapeutic. I'm focusing more on the idea of how trauma is cyclical, and certain things that happen, years will pass and things will pop up that trigger you and how other people view you...It feels good to finally talk about it because I'd rather it be from someone who has been through it and to come from a female perspective because I don't see that,” she explained.

Immediately, movies like The Hurt Locker, Brothers, American Sniper, etc., come to mind, but it’s difficult to recall one from the perspective of a female soldier.

Anna continues, “The military is a hugely diverse group of people. That's another thing that annoys me about film and TV, it’s extremely Black, Brown, Asian, not just White. There's so many different types of people and so many reasons as to why we joined--it doesn't all come down to people who just want to shoot guns and wear uniforms. Most of us were just trying to find a way to make our lives better because we had no other options like trying to escape gangs or we couldn’t afford college.”

Although there were setbacks along the way, Anna found her way back to writing, and she credits her big leap--applying to graduate school—to Stowe. She explains, “Stowe was one of the places that kind of convinced me I should go for it because that community helped me produce so much work and inspire me because of the people, because of the enthusiasm. Everyone has so much passion for what they do.”

After quitting her job as a copywriter in advertising, which she realized she hated and was creatively draining her, she dove back into writing—completing her first pilot—and started doing sketches with Upright Citizens Brigade. A friend sent her a link to apply with her pilot “just to see what would happen,” and Anna got in. But not just accepted, Ann was a finalist for the Final Draft fellowship and ended up getting a partial scholarship.

She surprised herself, but what surprised her most was the community and how expansive, but tight-knit and supportive it was.

“Both the Davids are so invested. It honestly amazed me how well they knew everybody's scripts and would come up and pull out lines from it. And even after you leave, they'll still keep in touch and be like, ‘Hey, there was this thing and it reminded me of a thing in your scripts—I wanted to say hi.’ Like there's so much love that comes from the top and all of the mentors,” Anna explained.

She continues, “But I really just think being surrounded by other people that are doing exactly what you want to do, helps it feel like it's a more tangible goal, that it's not just this thought you had in your brain and realize, ‘Well, it's never going to happen.’ It can. Every time I get updates about somebody who's a Stowe alum and something really great is happening with their work, I get inspired. Because we all go through that experience—constantly in this vacuum in your own head, suffering from imposter syndrome—and being in that community will make you want to work harder, and maybe actually feel like you have the right to call yourself a writer.”


Marian Cook is a former journalist, Stowe Story Labs staff member, and current USC student pursuing an MFA in directing. She’s been published over a dozen times, covering topics from local news to federal healthcare legislation. Although she loves the world of journalism, having done documentaries on a range of topics from plastic surgery to segregation in the church, her real passion lies in narrative film. She one day hopes to be a writer-director and tell strong, female-led stories, especially that of Latinas. When she’s not filming, she likes to explore, listen to blues and jazz, brush up on her French, and absorb everything science fiction related. Learn more at http://mariandcook.weebly.com/. At Stowe Story Labs, Marian assists with all aspects of operations, writes for the newsletter, and assists with research and writing to support fundraising and communications about programs.

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