Chester Gregory is a multi-award-winning actor and singer. A native of Gary, Indiana, Gregory worked as a teacher for the Lake County Public School System by day, and moonlighted as an actor in Chicago’s theater scene at night. Gregory wrote and produced plays and musicals for his students, nurturing their creative talents to become successful working professionals. He became a full-time actor and performer soon after landing the lead role in the critically acclaimed stage play The Jackie Wilson Story (which had a three-year run of sold-out performances) at the Black Ensemble Theatre in Chicago. Gregory has since performed all over the world in iconic roles on stage and on screen.

The Jackie Wilson Story culminated at New York’s Apollo Theater and received rave reviews from the New York Times. In 2003, Gregory’s award-winning depiction of Jackie Wilson gave him the opportunity to perform for the legendary “King of Pop,” Michael Jackson, who gave Gregory a standing ovation. That same week, Gregory made his Broadway debut as Seaweed in the Tony Award Winning Musical Hairspray, and he went on to originate and star in many Broadway musicals including Tarzan, Cry-Baby, Sister Act, and August Wilson’s Fences and Two Trains Running. He also performed internationally while touring with Motown the Musical, Dreamgirls, and Sister Act.

Gregory’s television and film work include roles in Revival! produced by Harry Lennix, Ish, The Testing Camera, and American Dreams and Films produced by Todrick Hall. He has also appeared on The Daily Show (Comedy Central), The View (ABC) and David Tutera’s CELEBrations with Kym Whitley.

In April 2022, he had his film debut playing Duke Ellington at Remember Me: The Mahalia Jackson Story, directed by Denice Dowse.

Gregory has received multiple awards throughout his career including an NAACP Theatre Award and a Joseph Jefferson Award. He also had the prestigious honor of receiving the key to the city in his hometown of Gary, Indiana, as well as East Chicago. Other awards include the Black Theater Alliance Award, the Black Excellence Award, the Special Recognition Award from the National Black Theater Festival, N.Y. Post Favorites and Broadway World.

In the spring of 2013, Gregory created, produced and starred in the one-man show, The Eve of Jackie, which premiered in New York to sold out audiences at 54 Below and at Chicago’s Black Ensemble Theatre. That summer his production was selected to headline The National Black Theatre Festival. To date, Gregory continues to perform The Eve of Jackie to sold out audiences across the country. Gregory is always developing, producing, and performing in new projects. He has relocated from New York to Los Angeles where he is transitioning his work from stage to television and film.

“A show of such physical and vocal dexterity…“
– The New York Times