Leo Schilling

filmmaker & actor

Born Leonardo Wilder Schilling, Leo’s parents serendipitously named him after the Academy Award winning filmmaker, Billy Wilder. Little did they realize that Leo would one day strive to actually follow in Mr. Wilder’s footsteps and forge his own legacy in the world of film.

Born Leonardo Wilder Schilling, Leo’s parents serendipitously named him after the Academy Award-winning filmmaker, Billy Wilder. Little did they realize that Leo would one day strive to actually follow in Mr. Wilder’s footsteps and forge his own legacy in the world of film.

Growing up in the Cayman Islands, Leo had the chance to explore the world with his family during most school breaks. At 11 years of age, Leo began his journey as a travel enthusiast, and budding filmmaker. He began creating vlogs to document his globetrotting adventures with his family. Fueled by a passion to create, Leo quickly fell in love with the process of editing his movies, often spending countless hours perfecting his creations.

During the challenging days of the Covid-19 lockdown in the Cayman Islands in 2020, Leo decided to expand his love and knowledge of aviation and dedicated over 80 hours to flight training, learning how to fly a helicopter. Part of that training involved flying 100 miles over open water from Grand Cayman to the sister island, Cayman Brac. In addition to these accomplishments, Leo started martial arts training and volunteered his time and skills to support younger kids at an MMA camp during lockdown.

Throughout high school, Leo devoted much of his time toward community service in various ways: from participating in monthly beach-cleanups to creating a short documentary about the Cayman Islands Documentary Film Festival in 2022. This was a breakthrough in Leo’s accomplishments as he began to realize that he found joy by leaving an impact on people through creating films.

Leo also realized he enjoys being in front of the camera, having had the opportunity to act in the newly released film, The Baker, featuring Ron Perlman. Being on the set, he was fascinated by the energy and excitement in the air and the carefully orchestrated ballet of intricacies of all that is required to put together a full-fledged motion picture. Leo then had the opportunity to work as an extra on the set of The Retirement Plan, a film shot in the Cayman Islands towards the end of the pandemic.

Then, in fall 2022, Leo made the bold decision to leave his beloved home in the Cayman Islands and moved to New York in pursuit of new life experiences. He was accepted to The Masters School, a renowned boarding school known for the arts, where he began taking advanced acting and film classes. Realizing that being on stage would give him a fresh perspective and make him a better director, he joined the school’s cast in Zombie Prom.

In the summer of 2023, Leo attended the Filmmaking Intensive at Pepperdine University in Los Angeles, California. This experience further solidified his dedication and passion for a future in the world of film.

Leo is not only a gifted filmmaker but also an exceptional long-distance runner. His personal accomplishments include running two full marathons at ages 13 and 15. With a 5k time of 16:58, his sweet spot is the 10k and half marathon. He has consistently won First Place in the under-19 category at the Long Beach Half Marathon, three years in a row. With a finish time of 1:23:34, Leo has earned a top-60 rank out of 7600 for three consecutive years in the Long Beach Half, including the October 2023 race. Furthermore, his leadership skills have led the Masters track team from 9th place to an impressive 2nd place within the region in just one year.

Leo also enjoys swimming, traveling, playing the steel pans, and spending time with friends and family. After he graduates in June 2024, he plans to begin university or film school in the fall of the same year, in order to continue honing his craft.

Leo is a well-cultured, passionate, and motivated young man, who strives to constantly expand his knowledge. Leo is often referred to as a Renaissance Man. He has very diverse interests that speak to his quirky and creative personality and has always been intrinsically motivated to challenge himself in all aspects of his life. In the short time that he has been at The Masters School, his expertise in the filmmaking industry has grown exponentially, and he continues to explore his interest in acting. Leo is constantly challenging himself to be the best version of himself, with a daily regimen full of study, cross-country and track and field practice, film and acting classes. Leo’s active involvement in his school community has enabled him to flourish as a filmmaker, actor, content creator, and artist.


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Aerial & Helicopter

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Cayman Documentary Film Festival


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I got the chance to chat with Leo over various crew dinners throughout my time on The Retirement Plan and was impressed by his enthusiasm and knowledge of movies and the industry.

Jackie Earle Haley, American Actor & Director

Many people I have taught over the years in martial arts, leadership training & stunt work/choreography have skills & talent but yet lack the drive & passion to fully realize their potential. Leo possesses both of those aspects which is why I truly believe that he will not only become an incredible film maker one day but will also be an amazing addition to any group/team that he works with.

Ronnie James Hughes, Director, The Academy Grand Cayman

Although our meeting was brief, Leo’s obvious desire to be a film maker was evident & left a nice impression on me.

Elias Koteas, Canadian Actor

I have been producing films for 25 years and have employed many young people over that time and Leo stood out to me for his natural aptitude and intelligence.

Nicholas Tabarrok, Producer, The Retirement Plan

For those of you who haven’t already, meet Leo Schilling, a new junior who hails from the Cayman Islands. Schilling is a man with a great variety of interests such as aviation (he knows how to fly a helicopter), film production, and acting, but another one of these interests is running. Schilling has been running for four years now. …

Repeat hill runs on the steep driveway behind Estherwood. Endless miles logged on the Old Croton Aqueduct alongside teammates. Countless weights lifted in the gym and sweat poured on the Greene Family Field track.
All of it added up to a phenomenal start to the 2023 season for the varsity boys cross-country team. …



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