Chester Gregory

Early life and education

Chester Gregory, Jr. 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.

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 he was accepted on his third by the time he reached high school.

He progressed to 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.

After graduating, Gregory began teaching acting classes and directing several productions at East Chicago Central High School and Indiana University Northwest.

Acting career

Gregory landed the lead role in Chicago's Black Ensemble Theatre's production of The Jackie Wilson Story, for which he received major 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 award-winning 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.

He then 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. Gregory has made several television appearances including The View, The Daily Show with Jon Stewart and American Dreams. Film credits include Hairspray.

In the spring of 2013, Gregory produced his own show titled 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. Immediately after, Gregory returned to his originating role as Officer Eddie Souther in Sister Act's national 2013-2014 tour.

In March 2015, Gregory was cast in the Goodman Theatre's revival of August Wilson's Two Trains Running in the role of Sterling, a role that earned legendary actor Laurence Fishburne a Tony Award in 1992. 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.

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. He's expected to remain in the show through its return to Broadway in the summer of 2016.

Recording career

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, Dave Tozer, 88-Keys, 9th Wonder, Cory Henry, and Chance The Rapper

Broadway roles

Television appearances