Photo courtesy of Cayleigh Pine
Held up to the screen was a book of 10 pieces of yellow construction paper stapled together. On the front page was a crayon sketch of a woman, dressed in an orange-and-black striped skirt matched with a large top hat. Etched across the page in young handwriting was the title: “The Strange Lady.” That was Cayleigh Pine’s first story. She tells me about this as we sit on a Zoom call, minutes after meeting for the first time. Her cheeks are flushed with slight embarrassment, but her eyes are determined. A determination that’s earned, considering she recently released “The God Couple,” her first short and the pilot to a series that she both acted in and directed, which has also been awarded Best Student Web Series/TV at the IndieX Film Fest.
Pine’s interest in film isn’t anything new. She grew up in Fort Lauderdale, Florida, where she was always involved in community and school theater. After realizing her interest in film during her senior year of high school, she moved to Boston to study film and psychology at Emerson College. Now, she is working in Los Angeles as an alternative series and specials intern at ABC while finishing up her last year of school. She traces her interest in film back to watching Disney Channel classics like “Hannah Montana” and “Wizards of Waverly Place.”
“It was a form of escapism for me to be writing these stories or watching these shows, because I wasn’t having a good time at school,” Pine explains. “When I would come home, I would just turn on the TV, and I had friends. And I was in a different place. And I could be a different person.”
She continues, “That’s what led me into acting. Because when you’re acting, you’re not really you — you’re a different person, or maybe even a better person than who you are.”
Her eyes bounce across the room, above the screen, out her window, as she describes her addiction to these shows, her investment in the arcs of each character, and her urge to disappear into worlds outside her own. But I’m curious to hear more about “The Strange Lady.” I ask what inspired it, and, for the first time during our conversation, Pine is still for a moment. She leans back in her chair as she brushes her hand through curls long enough to touch her waist.
“I wrote about this little girl who goes to an orphanage and then meets this witch who takes her and other children in. I don’t know what inspired it. I just started to write because it was fun.”
Her interest in books came a bit later when her dad suggested she read rather than watch TV all the time. She stumbled upon “Percy Jackson,” then “Harry Potter,” and then “The Hunger Games.” It was through reading these books that she discovered fantasy to be one of her favorite genres. As she got older, her interest in storytelling for fun morphed into a lonely pressure to become an acclaimed writer. She went to a high school focused on STEM fields rather than the arts, making it difficult to find a community of peers with similar interests. It wasn’t until Emerson that she felt seen in her love for filmmaking. She began working on sets, creating shorts, writing and even submitting to contests.
“Emerson was so different because it’s a very small art school. I felt like I was in high school 2.0 in an alternate universe where the arts were appreciated.”
Beyond learning the technical skills of storytelling, Emerson gave Pine the chance to refine her understanding of originality, or rather, taught her to avoid originality. This may sound contrary to what is commonly understood about creating, but she explains that she considers each person to be a mosaic, made up of bits and pieces of their communities, favorite TV shows, certain traits picked up from characters, and memories and experiences. What separates each individual, what brings in that “originality,” is not the novelty of each piece of the mosaic, but rather how these pieces fit together, how each individual is structured.
“I don’t think that the next great movie is going to be the most original thing in the world. But it could be different. Different is different than being original. Like when a musician plays a melody, they think it’s original. But maybe it’s been in five different songs, and they don’t realize it. That’s what it’s like when filmmakers try to make an original idea. It’s already been in five different movies. So okay, I’m out of original ideas, but I can still be creative. I can still make it different.”
She utilized this understanding when working on “The God Couple.” The idea for the short first came to her during winter break of her freshman year of college. She employed one of her favorite writing techniques: taking two contrasting ideas or people and putting them together. For the title, “The God Couple,” she was inspired by “The Odd Couple,” a Neil Simon play about two completely opposite friends who end up living together. Pine had seen reimaginings of the play cast with two women, but she wanted to create a different take. When I ask her about this difference, she leans forward, face close to the screen, eyes bright and excitement tangible. She describes her brainstorming process in a quick succession of questions and answers.
What’s the biggest “odd couple” she could write about?
“Oh, an angel and a demon, obviously.” At the last word, she almost rolls her eyes, briefly showcasing the nonchalant and quick-witted side of her character, Lucy, in the short.
Now there are two teenage girls; one’s an angel. But what if the other one’s the devil?
“Well, that would be hilarious.” She again shakes her head towards me, curls rustling.
What’s the worst punishment a man could think of? What would be the worst thing a man could be turned into?
“It wouldn’t be death. It wouldn’t be, you know, starvation. It would be turning into a woman or, more specifically, a teenage girl.” Her voice raises at this last sentence.
With those concepts, Pine began to fill out the story. She was intentional in creating female characters infused with complexity. When writing the short’s version of Lucifer, named Lucy, Pine aimed to create a villain who was calm and collected, an asshole with no manners. For Gabby, the angelic character, she juxtaposed a sweet disposition with cunning intentions.
It took the next three years of planning, writing and rewriting, casting, and shooting to produce the 20-minute series pilot. The time and effort spent are evident while watching the short. Pine’s attention to detail in how Gabby and Lucy are dressed, in the colors of their nails, and in the cuts from shot to shot is notable and impressive. Pine also directed the short while playing Lucy. Her dual role in the making of the film was something that she faced backlash for, especially from the predominantly male population within the film program at Emerson. “When I’ve directed men, there are some who are great and responsive. But there are times when some would make comments to take you down when you’re in a position of leadership. It’s very odd because it’s like, did we forget that you’re reading off of the script that I wrote? When I’m directing men, I’m being evaluated, and I have to prove myself.”
Filming “The God Couple” — making a short film that resonated with the female audiences Pine cares so much about — became a way to navigate this unfortunate scrutiny. “A lot of women from my college would message me after they watched the film, or they would approach me and they would say that they hadn’t seen something like this from our college in a long time.” It also allowed her to reflect on her own privilege within the industry. “With men, particularly white men, they are more open to letting a white woman into their spaces than a woman of color. I work to include as many people with different experiences as I can on my sets, but I acknowledge my own privilege and access to resources.”
Since creating “The God Couple,” Pine has learned to trust herself and all of the pieces that compose her own artistry. As she looks ahead, she plans to complete filming the rest of the series, and continue to tell stories. Her advice for up-and-coming filmmakers reflects her self-empowered approach to her work: “If at the end of the day, you feel like you cannot do something, or you aren’t passionate about what you’re doing or you are not confident in what you are doing, it’s just not going to end up being a good final product.”
When this mindset doesn’t work, Pine focuses on completion. “A project can be horrible, but it’s a miracle that it’s finished because it’s very difficult to maintain that stamina throughout all phases of a film.”
And, even when completion feels insurmountable, Pine goes back to what originally prompted her interest in acting, writing and film: finding community and comfort in stories and characters. “If you’re going to start something, finish it — believe in it enough to finish it. Even when things feel hopeless, and you think ‘Nobody likes me and everyone hates me, and everyone hates this project.’ Don’t let the people down that you’re bringing on as your team because they’re gonna believe in you.”
With that, Pine looks back at the screen, returning her gaze from something off to the left. This time her eyes are filled with grounded optimism, rather than determination. Her work reflects that she believes strongly in community and that she devotedly hopes to uplift others who create, just as she has learned to uplift herself.You can watch “The God Couple” here. Follow Cayleigh Pine on TikTok and Instagram to stay updated on her latest projects!