The North Carolina Symphony previously featured Chester Gregory as a soloist in 2022 for Dancing in the Street: The Music of Motown and in 2024 for Let’s Groove Tonight: Motown Meets the Philly Sound.

Chester Gregory is a singer whose 2024/25 season includes appearances as a soloist with the Baltimore Symphony Orchestra and Kansas City Symphony. He is also an actor who starred in the national tour of Motown: The Musical as Berry Gordy. Broadway credits include Motown: the Musical, Hairspray (Seaweed), Tarzan (Terk, original cast), Cry-Baby (Dupree, original cast), and Sister Act (Eddie). The New York Times has called him “jaw-dropping... overflowingly charismatic.” Other theatre credits include August Wilson’s Fences and Two Trains Running. He has toured nationally with Dreamgirls and Sister Act, as well as his one-man show The Eve of Jackie Wilson. He first played Jackie Wilson in The Jackie Wilson Story, which launched at Chicago’s Black Ensemble Theatre and culminated at New York’s renowned Apollo Theatre.

Gregory’s awards include Chicago’s Joseph Jefferson Award and a NAACP Theatre Award. He has been presented the keys to the city both in his hometown of Gary, Indiana, and in East Chicago. He has also been chosen as an Honorary State Representative of Indiana and received an honorary doctorate from his alma mater, Columbia College Chicago. He releases music under the name C.H.E.S.S., including the 2022 album Retrograde (Moon), and is currently producing several projects and recordings.