Dr. Chester Gregory, is a multi award winning actor, singer and producer.
Chester Gregory, II was born in Gary, Indiana to a steel mill worker, Chester Gregory, Sr., and school teacher, Edith Gregory. Growing up in the same hometown as Michael Jackson greatly inspired Gregory to become the artist he is today.
After years of performing in local talent shows and workshops for young performers, Gregory auditioned for the Emerson School for Visual and Performing Arts. His first two attempts were unsuccessful, but a third audition provided him the opportunity to attend by the time he reached high school. Upon Gregory’s graduation, his senior class voted him ‘Most Talented.’
This foundation laid the groundwork for his training at Columbia College Chicago, where he majored in Musical Theatre. Shortly before graduating with a Bachelor of Fine Arts degree, Gregory earned the leading role as Jesus in Jesus Christ Superstar. The production was co-directed by David Cromer.
Following graduation, Gregory began teaching acting classes and directing several productions at East Chicago Central High School and Indiana University Northwest.
He first emerged on the public scene in his award-winning portrayal of Jackie Wilson in The Black Ensemble Theater’s production of The Jackie Wilson Story. Gregory’s vocal range and acting prowess afforded him the lead role for which he received critical acclaim. The Jackie Wilson Story culminated at New York’s Apollo Theater and received rave reviews from the New York Times, which reported: “There is essentially one reason – and it’s a very good one – to see The Jackie Wilson Story, and that is the star: Chester Gregory.”
This role gave him the opportunity to sing for the legendary “King of Pop,” Michael Jackson, in 2003. Jackson gave Gregory a standing ovation for his performance that night, and a week later Gregory booked his debut Broadway role as Seaweed in the Tony Award Winning musical Hairspray, regularly garnering standing ovations and high praise from audiences and critics alike.
Following his successful run in Hairspray, Chester starred in the original Broadway cast of Tarzan as Terk, and Cry-Baby as Dupree. However, it was his 2009 performance as Jimmy Early in the national tour of Dreamgirls that compelled a New York Post theatre critic to say that Gregory’s performance “isn’t scene-stealing, but robbery on an Enron scale.” For this role, Gregory would go on to earn several additional accolades domestically and internationally. Immediately following Dreamgirls, he was cast as Officer Eddie Souther for the Broadway production of Sister Act.
In the spring of 2013, Gregory produced and starred in a more intimate look into the life of Jackie Wilson, The Eve of Jackie. Premiering in New York, Gregory performed to a sold-out audience at 54 Below, before bringing the show to Chicago’s Black Ensemble Theater for a sold out premiere. That summer, his production was selected to headline The National Black Theatre Festival. To date, Gregory continues to perform his one-man show The Eve of Jackie to sold out audiences across the country. His successful Broadway career has allowed Gregory to transition to TV and film work.
Gregory returned to his originating role as Officer Eddie Souther in Sister Act’s national 2013-2014 tour and in March 2015, was cast in the Goodman Theatre’s revival of August Wilson’s Two Trains Runningin the role of Sterling, a role that earned legendary actor Laurence Fishburne a Tony Award in 1992.
In January 2016, Gregory joined the touring cast of the Broadway production Motown: The Musical. In the show, Gregory plays the lead character, Motown founder Berry Gordy. Gregory remained in the show through its return to Broadway in the summer of 2016 and its 2017 national tour.
Dr. Gregory has received numerous awards including the Joseph Jefferson, NAACP Theatre Award and an honorary doctorate from his alma mater, Columbia College Chicago. He has also made several television appearances including The View, The Daily Show with Jon Stewart, American Dreams and a film credit in Hairspray. Aside from acting, Gregory worked on numerous albums and mixtapes before releasing “In Search of High Love”.
Gregory, who records under his artist name CHΞSS, has spent much of his career in the studio. He has worked with artists such as Phil Collins (Tarzan), Marc Shaiman (Hairspray and Catch Me If You Can) and Henry Krieger (Dreamgirls). For his album, In Search of High Love, he worked with industry greats including PJ Morton and Eric Roberson. For his mixtapes and other projects, he has collaborated with Ledisi, Dot Da Genius, Mali Music, 88-Keys, 9th Wonder, Cory Henry, and Chance The Rapper.