Chester Gregory
Updated: 12/10/2025, 9:07:57 PM Wikipedia source
Chester Gregory, also known as C.H.E.S.S. (born December 10, 1972), 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. Gregory's other credits include principal roles in Tarzan, Cry-Baby, Dreamgirls and Sister Act. Gregory produced and starred in a 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. He has been awarded the key to two cities: The key to his hometown the City of Gary, Indiana and the Key to the City of East Chicago, Indiana. He has also been awarded Honorary State Representative for the state of Indiana.
Infobox
Born
Chester Gregory Jr. (1972-12-10) December 10, 1972 (age 53)Gary, Indiana, United States
Other names
C.H.E.S.S.
Occupation(s)
Actor, singer, songwriter
Years active
1996–present
Spouse
Kimberly Hébert Gregory (divorced)
Children
1
Occupations
Actor, singer, songwriter
Tables
· Stage credits
2008
| Year | Title | Role | Theater | Notes |
| 2003 | Hairspray | Seaweed | Neil Simon Theatre | Broadway Debut |
| 2006 | Tarzan | Terk | Richard Rodgers Theatre | |
| 2008 | Shrek the Musical | Donkey | 5th Avenue Theatre | Seattle Pre-Broadway Try-out |
| 2008 | Cry Baby | Dupree | Marquis Theatre | |
| 2009 | Dreamgirls | James "Thunder" Early | Various | (National Tour) |
| 2011 | Sister Act | Eddie Souther | Broadway Theatre | Reprised the role on the 2012 National Tour |
| 2014 | Motown: The Musical | Berry Gordy | Nederlander Theatre | Replacement Barry on the original National Tour Reprised the role on Broadway in 2016 and again on the second National Tour |
References
- Chicago Tribunehttps://www.chicagotribune.com/news/ct-xpm-2010-01-17-1001160196-story.html
- Playbillhttp://www.playbill.com/article/run-and-tell-that-newcomer-chester-gregory-ii-to-be-seaweed-in-hairspray-com-113826
- www.broadwayworld.comhttps://www.broadwayworld.com/people/Chester-Gregory/
- Miami Heraldhttps://www.miamiherald.com/entertainment/performing-arts/article39334953.html#storylink=cpy
- The Michigan Chroniclehttps://michiganchronicle.com/2014/11/11/24th-annual-naacp-theatre-awards-honor-gylnn-turman-toni-braxton-and-roger-guenveur/
- "(VIDEO) Columbia College Chicago Alum Chester Gregory Stars in 'Higher and Higher' Aug. 25 at Marriott Theatre | Theatre Department: The Green Room"https://blogs.colum.edu/theatre/2019/08/23/video-columbia-college-chicago-alum-chester-gregory-stars-in-higher-and-higher-aug-25-at-marriott-theatre/
- "Columbia College Chicago's 'New York City Broadway Experience' Featuring Tony Award Winner David Cromer Raises $15,000+ for Columbia College Theatre Students | Theatre Department: The Green Room"https://blogs.colum.edu/theatre/2018/11/08/columbia-college-chicagos-new-york-city-broadway-experience-featuring-tony-award-winner-david-cromer-raises-15000-for-columbia-college-theatre-students/
- "Columbia College Chicago's 'New York City Broadway Experience' Featuring Tony Award Winner David Cromer Raises $15,000+ for Columbia College Theatre Students | Theatre Department: The Green Room"https://blogs.colum.edu/theatre/2018/11/08/columbia-college-chicagos-new-york-city-broadway-experience-featuring-tony-award-winner-david-cromer-raises-15000-for-columbia-college-theatre-students/
- Playbillhttp://www.playbill.com/article/liftin-me-higher-melba-moore-stars-in-jackie-wilson-story-at-nycs-apollo-april-3-opens-april-6-com-112414
- HuffPosthttps://www.huffpost.com/entry/the-eve-of-jackie-chester-gregory-jackie-wilson-show_n_2792554
- Greensboro News and Recordhttps://www.greensboro.com/entertainment/national-black-theatre-festival-chester-gregory-reprises-role-of-jackie/article_f22713fc-f49d-11e2-b969-0019bb30f31a.html
- BroadwayWorld.comhttps://www.broadwayworld.com/chicago/article/Chester-Gregory-Speaks-at-Columbia-College-Chicago-Receives-Honorary-Doctorate-20150519
- "Run and Tell That: Newcomer Chester Gregory II To Be Seaweed in Hairspray"https://web.archive.org/web/20041226131518/http://www.playbill.com/news/article/80195.html
- The New York Timeshttps://www.nytimes.com/2006/05/11/theater/reviews/11tarz.html?pagewanted=all
- "Chester Gregory | In Search of High Love"http://cdbaby.com/cd/cgregory
- "Chester Gregory Theatre Credits"http://broadwayworld.com/people/?personid=8469
- Hetrick, Adam (February 1, 2011). "Victoria Clark, Fred Applegate, Chester Gregory Will Be Part of Broadway's 'Sister Achttp://www.playbill.com/news/article/147227-Victoria-Clark-Fred-Applegate-Chester-Gregory-Will-Be-Part-of-Broadways-Sister-Act