Chester Gregory

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Chester Gregory
Born Chester Gregory II
(1978-12-10) December 10, 1978 (age 38)
Gary, Indiana
Other names C̤̈Ḧ̤Ë̤S̤̈S̤̈
Occupation Actor, singer, songwriter
Years active 1996-Present

Chester Gregory, also known as CHΞSS (born December 10, 1978),[citation needed] is an American actor, singer and songwriter from Gary, Indiana. His breakthrough came with his portrayal of Jackie Wilson in The Jackie Wilson Story, which led to his Broadway debut as Seaweed in Hairspray.[citation needed] Gregory's other credits include principal roles in Tarzan, Cry-Baby, Dreamgirls and Sister Act.[citation needed] Gregory produced and starred in a look into the life of Jackie Wilson in The Eve of Jackie.[citation needed] Gregory has received numerous awards including the Joseph Jefferson and NAACP Theatre Award.[citation needed]

Aside from acting, Gregory worked on numerous albums and mixtapes before releasing In Search of High Love.[citation needed]

Early Life and Education[edit]

Chester Gregory, Jr. was born in Gary, Indiana on December 10, 1978 to steel mill worker, Chester Gregory, Sr., and school teacher, Edith Gregory.[citation needed] Growing up in the same hometown as Michael Jackson inspired Gregory to become an artist.[citation needed]

After years of performing in local talent shows and workshops for young performers, Gregory auditioned for the Emerson School for Visual and Performing Arts.[citation needed] His first two attempts were unsuccessful, but he was accepted on his third by the time he reached high school.[citation needed]

He progressed to Columbia College Chicago, where he majored in Musical Theatre.[citation needed] Shortly before graduating with a Bachelor of Fine Arts degree, Gregory earned the leading role as Jesus in Jesus Christ Superstar.[citation needed] The production was co-directed by David Cromer.[citation needed]

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


Acting career[edit]

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[edit]

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).[citation needed] For his album, In Search of High Love, he worked with industry greats including PJ Morton and Eric Roberson.[citation needed] 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[citation needed]


Broadway roles[edit]

Television appearances[edit]


  1. ^ Hetrick, Adam (February 1, 2011). "Victoria Clark, Fred Applegate, Chester Gregory Will Be Part of Broadway's 'Sister Act'". Retrieved February 22, 2013.
  2. ^ Jones, Kenneth (June 17, 2003). "Run and Tell That: Newcomer Chester Gregory II To Be Seaweed in Hairspray". Archived from the original on December 26, 2004. Retrieved February 22, 2013. 
  3. ^ Brantley, Ben (May 11, 2006). "Tarzan Arrives on Broadway, Airborne". The New York Times. Retrieved February 22, 2013. 
  4. ^ Thomas, Don (April 16, 2003). "Chester Gregory, an electrifying Jackie Wilson". The New York Beacon.   – via HighBeam (subscription required)
  5. ^ "Chester Gregory Theatre Credits". Broadway World. Retrieved February 22, 2013. 
  6. ^ "Chester Gregory | In Search of High Love". CD Baby. Retrieved February 22, 2013. 
  7. ^ "Trapped in the Closet Pt. 1". The Daily Show with Jon Stewart. September 10, 2007. 
  8. ^ [1][dead link]

External links[edit]