Chester Gregory

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.

Reprised the role on Broadway in 2016 and again on the second National Tour

In 2015, Dr. Gregory founded a workshop titled “Manifest Your Inner Shine”. That same year he received his honorary doctorate degree from his alma mater, Columbia College, and had the honor of giving the commencement address. The following year Dr. Gregory founded Lucid Life, an organization and production company that provides workshops and master classes to high school students, college students, and artists who seek professional development. He has also lead acting and singing workshops at Donda’s House and other schools and organizations throughout New York, Florida, and the Chicagoland area.

In the spring of 2013, Dr. 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, Dr. Gregory continues to perform The Eve of Jackie to sold out audiences across the country.

The Jackie Wilson Story culminated at New York's Apollo Theater and received rave reviews from the New York Times. In 2003, Dr. Gregory met and performed for the legendary "King of Pop," Michael Jackson, who gave Dr. Gregory a standing ovation. That same week, Dr. Gregory made his Broadway debut as Seaweed in the Tony Award Winning musical Hairspray. He remained in the cast for two and a half years, then moved on to originate and star in other principal roles on Broadway including Tarzan (Terk), Cry-Baby (Dupree), Sister Act (Eddie Souther) and Motown The Musical (Berry Gordy). He also performed internationally while touring with Motown the Musical, Dreamgirls, and Sister Act. Other work includes August Wilson’s Fences and Two Trains Running.

Chester Gregory, also known as CHΞSS (born December 10, 1978), is an American actor, singer and songwriter from Gary, Indiana. His breakthrough came with his portrayal of Jackie Wilson in The Jackie Wilson Story, which led to his Broadway debut as Seaweed in Hairspray. Gregory's other credits include principal roles in Tarzan, Cry-Baby, Dreamgirls and Sister Act. Gregory produced and starred in a look into the life of Jackie Wilson in The Eve of Jackie. Gregory has received numerous awards including the Joseph Jefferson and NAACP Theatre Award.

Chester Gregory was born in Gary, Indiana on December 10, 1978 to steel mill worker, Chester Gregory, Sr., and school teacher, Edith Gregory. Growing up in the same hometown as Michael Jackson inspired Gregory to become an artist.

Gregory, who records under his artist name CHΞSS, has spent much of his career in the studio. He has released several albums and worked with music legends such as Phil Collins, Marc Shaiman, Henry Krieger and Artie Butler. Dr. Gregory worked with PJ Morton and Eric Roberson for his album In Search of High Love. Other collaborations include Ledisi, Keyon Harrold, Dot da Genius, MaliMusic, 88-Keys, 9th Wonder, The Pocket Queen, Cory Henry, and Chance The Rapper. Dr. Gregory has a new project titled RETRO(GRADE) under his artist name, CHΞSS.