Gregory’s acting work spans theatre, film, and television, with a focus on character driven storytelling and emotionally grounded performance. His approach as an actor is informed by decades of experience as a director, writer, and producer, allowing him to enter roles with a strong understanding of story structure, pacing, and collaboration.
Gregory began acting as a child and has performed in numerous plays and musicals in regional theatres, national tours, and New York City. He spent several years working in children’s theatre tours and received his Equity card through the Theatre for Young Audiences tour of Story Salad, which brought well known children’s books to the stage. These early experiences shaped his commitment to clarity, accessibility, and connection in performance.
On stage, Gregory has appeared in a wide range of productions including musicals, plays, and cabaret performances. His theatre work reflects a deep investment in ensemble driven storytelling and nuanced character development, shaped by years of experience both onstage and behind the scenes.
Gregory’s on camera work includes multiple appearances on Saturday Night Live, which led to his AFTRA card, as well as roles in the television series Tattingers. He also toured nationally in live productions including Teenage Mutant Ninja Turtles and The Attack of the Killer Tomatoes, and portrayed Striker the Mascot during the introduction of the character for the 1994 World Cup.
In film, Gregory has appeared in short and feature projects that explore intimate, human centered stories. His performances are rooted in authenticity and restraint, favoring emotional truth over spectacle. In 2023, he returned to working in front of the camera with roles in short films, commercial and UGC projects, and background television work on series such as Succession, HBO documentaries, and American Sports Story.
As an actor, Gregory is drawn to roles that explore identity, vulnerability, resilience, and moral complexity. He continues to pursue work that aligns with these values while remaining open to projects that challenge and expand his range.
Selected scenes from short films, showcasing character driven performances across dramatic and narrative work.
A short parody film featuring Gregory as Gordon Ramsay, blending horror tropes with dark comedy.