Chester Gregory

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Chester Gregory
Born Chester Gregory II
Gary, Indiana
Other names CHΞSS
Occupation Actor, Singer, Songwriter
Years active 1996-Present

Chester Gregory, also known as CHΞSS, 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 creating a buzz with his June 7, 2008 release, In Search of High Love. He is currently on tour with Sister Act and in the studio preparing his latest project, TRIFECTA.

Early Life and Education[edit]

Chester Gregory, Jr. was born in Gary, Indiana 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.

Acting Career[edit]

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.

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.

Recording career[edit]

Gregory, who records under his artist name CHΞSS, 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). 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 and 9th Wonder. CHΞSS is currently in the studio, recording new music for an upcoming project.

Broadway roles[edit]

Audio Discography[edit]

  • Breakbeat Karaoke
  • In Search of High Love - Chester Gregory
  • Tarzan - The Broadway Musical[7]
  • Shrek (Orchestra Test) - DreamWorks Theatricals
  • Hairspray - (Movie Soundtrack & Special Edition)
  • Carol's For A Cure Vol. 8
  • Chicago Soul Sessions
  • Catch Me If U Can (Pre-Brodaway Recordings)
  • Carol's For A Cure Vol. 6
  • New York City Christmas
  • Morning Starr- Ahdae
  • The McKenzie-Burns Project
  • Jackie Wilson Story Soundtrack - Black Ensemble

Television appearances[edit]

  • The Daily Show - W Jon Stewart, Comedy Central [8]
  • The View - Interview and performance with Rosie O'Donnell[9]
  • HAIRSPRAY -“Break Out” (Lead Vocal) New Line Cinema
  • ART BEAT News Chicago
  • DOTS (Pilot) NBC
  • "Grand Theft Auto” – Liberty City (Video Game) Rock Star Games

Awards and nominations[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". 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. ^ "Tarzan - The Broadway Musical (Original Broadway Cast) [Cast Recording]". Retrieved February 22, 2013. 
  8. ^ "Trapped in the Closet Pt. 1". The Daily Show with Jon Stewart. September 10, 2007. 
  9. ^ [1][dead link]

External links[edit]