Columbia College Chicago Theatre Department alum Chester Gregory ’95, HDR ’15, has released a new album, Remembering Jackie — a tribute to legendary 1960s soul star Jackie Wilson. Gregory, a graduate of the Columbia College Theatre Department’s BA Program in Musical Theatre, launched his career by starring at Chicago’s Black Ensemble Theatre in The Jackie Wilson Story, a hit musical biography of the late singer.
After relocating to New York, Gregory starred on Broadway in such musicals as Hairspray (as Seaweed Stubbs), Sister Act, Tarzan, and most recently Motown the Musical, in which he portrayed Motown Records founder Berry Gordy.
Gregory also starred in national tours of Hairspray, Motown the Musical, Sister Act, and Dreamgirls (in which he played Jimmy “Thunder” Early) as well as his own one-man Jackie Wilson tribute The Eve of Jackie, which he performed at the 2015 National Black Theatre Festival in North Carolina. He has also acted in regional theatres across the U.S., including productions of dramas by August Wilson at Chicago’s Goodman Theatre and the Kansas City Repertory Theatre. He now lives in Los Angeles, where he is slated to star in the musical revue Blues in the Night April 27 through May 20 at the Wallis Annenberg Center for the Performing Arts.
In 2015, Gregory was a commencement speaker at Columbia College Chicago’s graduation ceremony and received an Honorary Doctorate from the college.
Produced by Etienne “EJ” Porter and Gregory, Remembering Jackie features Gregory’s interpretation of some of Wilson’s timeless hits, including “Lonely Teardrops,” “(Your Love Keeps Lifting Me) Higher and Higher,” “To Be Loved,” “Reet Petite,” and more. For Gregory, this project is a chance to further celebrate the legacy of Wilson, who was famed for his athletic, highly emotional performing style. “I wanted to honor the requests from supporters who have been asking me to record this music for years. However, I didn’t want to simply cover his songs. I had to interpret them in my own voice, emulating how he’s inspired me and honoring the sound of the era with a modern spin. Remembering Jackie is a keepsake, a soundtrack, and bridge across generations.” Listeners can stream Remembering Jackie on Apple Music, TIDAL, and all major streaming platforms today.