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Venture into the world of storytelling and artistic creation, and you'll find Chester Gregory, a visionary director whose unique and diverse experiences have left an indelible mark on the stage, screen, and beyond. With a prolific career spanning decades, he has skillfully guided productions that evoke emotions, provoke thought, and celebrate the human experience.


Staging Memorable Productions:

🎭 A MOTOWN CELEBRATION (2022 - Present) - Embarked on a musical journey through time, directing a captivating homage to the iconic Motown era. The stage comes alive with timeless melodies and legendary artists that have shaped generations.

🎭 THE EVE OF JACKIE WILSON (03/2013 - 2022) - In a powerful collaboration, co-directed a soul-stirring tribute to Jackie Wilson, blending narrative and music to honor the life and legacy of a true musical legend.

🎭 WEST SIDE STORY (03/2020) - Crafted a captivating rendition of the classic musical, bringing the timeless tale of love and conflict to life with a fresh perspective.

🎭 THE WIZ JUBY (03/1999) - Infused boundless energy and creativity into a vibrant adaptation of the beloved musical, captivating audiences with its iconic characters and infectious music.

🎭 JUVIE (01/1999) - Explored the depths of emotion and redemption in a poignant short film, shedding light on the challenges faced by young individuals within the juvenile justice system.

🎭 A JOURNEY THROUGH A KING'S LIFE (THE STORY OF MARTIN LUTHER KING) (03/1998) - Penned and directed an inspiring play that delves into the remarkable journey and enduring legacy of Martin Luther King.

🎭 COMMON SENSE (09/1998) - Provoked thought and discourse with an engaging play that tackled pertinent social themes through a creative narrative.

Bringing Music to Life:

🎬 Short Films Directed and produced captivating music videos that transcend sound, including "ZODIAC KILLA" (12/2022) and "NATIONAL ANTHEM (ANOTHER ONE)" (07/2020), each capturing the essence of the music and resonating with audiences.

🎬 THE DOPPLER EFFECT (IT’S ME), Producer (04/2020) Produced a music video that garnered critical acclaim and earned consideration for a prestigious Grammy award, showcasing his prowess as a visual storyteller.


Dived into the world of television with "THE ROOT OF IT," an innovative interview series that marries two passions—people and vegan food. Directed and produced the pilot episode and trailer, combining entertainment with education.

📽️ Short Form Commercials

Collaborated with notable brands such as Popeyes, Cleo Banking App, GPods, and Sling TV, bringing their stories to life through captivating short-form commercials.


A Multifaceted Creative Force

With a career that encompasses directing, producing, writing, and performing, Chester Gregory has effortlessly woven his artistic talents into a rich tapestry of creativity. His influence extends beyond the stage and screen, touching hearts, minds, and inspiring countless individuals. From thought-provoking productions to visually striking music videos, Chester Gregory's work continues to resonate, entertain, and enlighten.

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