Chadwick’s school spirit makes many alumni reminisce about their high school days, but one experience trumps all at reunions: the senior year Outdoor Education (OE) trip. The unique opportunity to go into the wilderness for three weeks with friends extends to very few other schools across the United States. Chadwick alumni Grace Gay ’18 and Thomas Winter ’18 have created a spin on Chadwick’s legacy in the form of a workplace sitcom spotlighting the experiences of OE instructors.
Gay, the writer, director, and producer of the TV show pilot, called Outdoor Educators, began brainstorming the idea of an outdoor education-related TV show while trying to create a second sample for the Warner Bros. Discovery Access Writers Program. She then shared her idea with her family and friends, whose reactions encouraged her.
“This was the first time I had sent something out and, universally, people were like, ‘We want to see more. We would love to see this as a TV show,’” Gay said.
After her early conceptual successes, she reached out to people she knew in the industry or found on social media to join the project. Diversity was an important consideration for Gay in choosing the cast and crew.
“I really wanted an Asian male lead because I feel like there’s not a lot of great Asian male representation in TV and film,” Gay shared. “I also felt like there’d be a lot of room for diversity. This could be a show where we have a crew and a cast of mostly people of color and women.”
Gay also reached out to multiple Chadwick alumni in the film industry about joining the project, and she received positive responses from several. However, Winter was the only one to stick around.
Since graduating from Chadwick and studying theatre and economics at USC, Winter has appeared in many different productions and has credits in musicals, short films, TV series, and video games.
Even though the series took inspiration from their experiences as students in Chadwick’s OE program, the series focuses on the program’s instructors. Winter plays one of these instructors, named Cliff, who deals with various insecurities about his lack of experience.
The pilot was filmed over the course of four days in locations across Los Angeles, including Silver Lake and Santa Clarita. But Winter and Gay’s favorite day of filming was the third day, when they filmed on Chadwick’s campus, just outside of Roessler.
“Filming at Chadwick was a really great day because everyone was able to see the real location that we departed from [for OE trips], and they were able to kind of ground themselves in that reality that we all experienced,” said Winter.
Winter and Gay may not have gotten to visit any Chadwick teachers while on campus, as they filmed on a Saturday, but they’ve both stayed in contact with some of their former teachers, including several who still work at Chadwick.
Associate Director of Admission David Bloom worked closely with both Winter and Gay while they were in the Upper School, as they were both members of Chadwick’s Jubilee Singers group, which Bloom founded and led.
Bloom also collaborated with Gay as a faculty coordinator for the Black Student Union, which Gay helped lead.
“Grace is really funny and dynamic,” Bloom said. “She’s also very committed to social justice and was a central figure in making sure students and faculty were held accountable for making Chadwick as inclusive as possible.”
Bloom taught Winter in a 9th grade theater class as well as Jubilee Singers and described him as “someone who makes everyone feel valued and heard when entering the room.”
Bloom also noted Winter’s talent in performance: “His sincerity as a human matches his sincerity as a performer.”
Upper School math teacher Michael Cass, who’s also the head of the Chadwick Improvisers (ChImps), knows Winter well, as Winter participated in ChImps and regularly returns for alumni shows.
“[Winter] is one of my favorite people,” Cass shared. “He’s an incredible improviser with a gift for acting and innate kindness and gratitude.”
“I’m not surprised that [Winter and Gay] are doing creative things out in the real world,” added Erin Nordlund, the Assistant Head of School for Teaching & Learning. “They’re both great storytellers. They’re just smart, creative people who are such good examples of joyful humans.”
All of these teachers are thrilled that their former students are working on such an ambitious project and are very excited to see the pilot when it is released.
Gay plans to submit the pilot to film festivals such as the African American Film Festival and the Indie Pilot Showcase once post-production work is done. After the festival results come out, Gay wants to release the pilot to the public on YouTube.
While Gay and Winter may not know what lies ahead for their creative work, they hope that their efforts can inspire other young people, especially Chadwick students, to follow their passions.
“Sometimes your path is just going to look a lot different than other people’s, especially if you’re going to be an artist. It’s important to keep your head steady and remember what you want to do and why you’re doing it,” Gay said. “You don’t want to wake up one day when you’re fifty-five and wish that you had pursued theater.”
Winter agreed: “Follow your joy, and the rest will come.”
