NAACP Theater Award Winner Chester Gregory was born and raised in Gary,Indiana where at young age he fell in love with performing.. Influenced by the entertainers of his childhood, he found his own unique voice and style.

Chester studied and refined his skills in singing and acting at Emerson Visual and Performing Arts School, and Columbia College, graduating with his Bachelor of Fine Arts degree. Through dedication and hard work he built his passion for the arts into a career, making a name for himself when he burst onto the theater scene as Jackie Wilson in original production of “The Jackie Wilson Story” for which he received major acclaim such as, The Jeff, AUDELCO, BTAA and Black Excellence Awards. His first ever review in The New York Times begins: “There is essentially one reason — and it’s a very good one — to see ”The Jackie Wilson Story,” and that is the star, Chester Gregory.”

The award-winning role gave him the opportunity to sing for the legendary Michael Jackson in 2003. Also known as “The King Of Pop” he has impacted millions around the world, and has been a huge personal inspiration for Chester. The two in fact shares a hometown. That night Michael gave Chester a standing ovation for his performance, and later that week Chester would book his debut Broadway role as Seaweed in the Tony Award Winning Musical Hairspray.

Chester went on to star in the original Broadway casts of “Tarzan” (as Terk) and “Cry-Baby” (as Dupree). In 2009 he went on tour again, this time with “Dreamgirls”, and was awarded Best Supporting Actor by the NAACP Theater Awards and garnered accolades around the world, including both the United States and Japan, for his powerful performance as Jimmy Early.

Chester is currently starring in the smash-hit Broadway musical “Sister Act” as Officer Eddie Souther, and earned an Outer Critic Circle Award Nomination for this role. Though widely celebrated as a talented actor, Chester remains true to his love of music and has produced three solo recording projects, his debut album “In Search of High Love,” his mix-tapes, “Breakbeat Karaoke,” and “If U Only.” To see him live in performance is to see Chester in his most natural element. Whether in a theater or concert venue, Chester Gregory is always magnetic and incredibly dynamic. He shines brightest on the stage! Find his latest performances and music at