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Chester Gregory II

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), is an American actor, singer and songwriter from Gary, Indiana. He first emerged on the scene in his portrayal of Jackie Wilson in The Jackie Wilson Story, which led to his Broadway debut as Seaweed in Hairspray. Gregory's other credits include principal roles in Tarzan, Cry-Baby, Dreamgirls, Sister Act and performing for Michael Jackson. After garnering acclaim, Gregory produced and starred in a more intimate look into the life of Jackie Wilson in The Eve of Jackie. Gregory has received numerous awards including the Joseph Jefferson and NAACP Theatre Award.

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

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, greatly 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 a third try 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.

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

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 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.


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