Chester Gregory

Chester Gregory is an award-winning Broadway veteran and recording artist. The New York Times calls him, "jaw dropping...over flowingly charismatic," stating “Gregory has the audience eating out of the palm of his hand.” His Broadway credits include starring in Motown: The Musical (Berry Gordy), Hairspray (Seaweed), Sister Act (Eddie), Tarzan (Terk, Original Cast), and Cry-Baby (Dupree, Original Cast). National tours include Motown: The Musical (Berry Gordy), Sister Act (Eddie), and Dreamgirls (James “Thunder” Early). Gregory's breakthrough role came with his outstanding portrayal of Jackie Wilson in The Jackie Wilson Story, launched at Chicago's Black Ensemble Theatre and culminated at New York's renowned Apollo Theatre. Regional theatre credits include Shrek (Donkey), Fences (Lyons), and Two Trains Running (Sterling). Television appearances include performances on The Daily Show, The View, and The Tony Awards. As a recording artist, Gregory, also known as CHΞSS, has collaborated with industry greats including Phil Collins, Marc Shaiman, Ledisi, and Chance The Rapper. Studio recordings include multiple singles, Original Broadway Cast recordings, and his album In Search of High Love. He is the recipient of Chicago’s Jeff Award, the NAACP Theatre Award, the key to the city of his hometown of Gary, Indiana, as well as an honorary Doctorate Degree from Columbia College Chicago. Concerts include Higher and Higher with Artists Lounge Live and his original concert The Eve of Jackie.