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About Chess

chester gregory about 1Born in Gary, Indiana to a steel mill worker and a school teacher, Chester “CHΞSS” Gregory drew inspiration from hometown hero Michael Jackson to pursue his dream of becoming an artist.He began his journey performing in local talent shows and participating in workshops for young performers.

After a few years, Gregory was ready to take the next step and auditioned for the Emerson School for Visual and Performing Arts. Although his first two attempts were unsuccessful, Gregory didn’t give up, and his third try provided him the opportunity to attend by the time he reached high school. A testament to his gift, he was voted ‘Most Talented’ his senior year of high school.

chester dreamgirls splitUpon graduating high school, Gregory began attending Columbia College, where he majored in Musical Theatre. Here Gregory was able to hone his skills and lay the groundwork for his foundation as a performer. Shortly before graduating with a Bachelor of Fine Arts degree, Gregory earned the leading role as Jesus in Jesus Christ Superstar. After graduating, Gregory began teaching acting classes and directing several productions at East Chicago Central High School and Indiana University Northwest.

Shortly thereafter, Gregory’s vocal range and acting prowess afforded him 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 famed Apollo Theater and received rave reviews from the New York Times: “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.”

chester TTRThis 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.

chester gregory about 4In 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 2015, Chester Gregory appeared in his very first August Wilson play—Two Trains Running, directed by Chuck Smith, in the role of Sterling. Mr. Gregory has received many awards including the Jeff Award and NAACP Theatre Award, and has been presented the key to the city of his hometown of Gary, Indiana, as well as East Chicago. This spring, Chester was presented with an Honorary Doctorate from his alma mater, Columbia College Chicago.

In addition to acting, Gregory has spent much of his career in the studio. He’s worked with legends such as Phil Collins (Tarzan), Marc Shaiman (Hairspray and Catch Me If You Can) and Henry Krieger (Dreamgirls), as well as industry greats including PJ Morton and Eric Roberson. He released his first album, In Search of High Love, in 2008 and has worked on several other mixtapes and projects. He has collaborated with the likes of Ledisi, Dot Da Genius, Dave Tozer, 88-Keys and 9th Wonder. Chester currently records under his artist name, CHΞSS, and is working on a new project.


  • Little Light

    June 27, 2015
  • Imagine

    June 27, 2015
  • Mad World

    June 27, 2015
  • I Can’t Tell You Why

    June 27, 2015
  • What Makes You Beautiful

    CHESS WMYB (What Makes You Beautiful)

    June 27, 2015

The Eve Of Jackie

Award-Winning Actor Chester Gregory channels the dynamic spirit of Jackie Wilson: “Mr. Excitement”, one of the most influential artists in rock ‘n’ roll history, Live in concert, on an evening when he feels compelled to reveal his personal journey in show business.

During this night, he shares his thoughts on the valleys and peaks in his personal life and career in show business. He is unaware that it will be his final performance in completion, as it is the evening before his inevitable collapse on stage the following day… September 29th, 1975.

Catch Gregory in this heartfelt portrayal that will unite generations young and old. Don’t miss what audiences & critics call “the performance of a lifetime”.

“...Gregory captured the essence of Wilson. Possessing a vocal tone and range similar to Wilson’s Gregory channeled his idol through a performance in which he replicated the singer’s falsetto, signature choreography, passion and inexhaustible energy”
- The Examiner

"Mr. Gregory puts on a show of such physical and vocal dexterity that it's almost impossible to imagine that anyone else could do it."
- The New York Times




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