BWW Interviews: Chester Gregory of SISTER ACT: THE MUSICAL

Chester Gregory is currently in Nashville with the national tour of Sister Act: The Musical. He plays Sweaty Eddie, one of the lead characters in the show. Chester originated the role of Sweaty Eddie on Broadway, and has joined the touring cast to revisit the role. Despite his busy schedule, Chester took some time from his day to answer a few questions for us here at Broadway World, and to share a little about himself and about Sister Act: The Musical.

BWW: Chester, you have quite the resume. Shows like Hairspray, Tarzan, Cry Baby, and of course, the original cast of Sister Act on Broadway, as well as a host of other credits.Do you have a role that you are most proud of or that you had the most fun with? Or perhaps a role that you connected to the most?

CG: One of the roles I'm most proud of is definitely portraying Jackie Wilson. Twice! Once in a show called The Jackie Wilson Story and currently with a project I produced called The Eve of Jackie. It's an honor to portray this legend and it has certainly changed my life. It actually helps me land my Broadway debut as Seaweed in Hairspray.

BWW: You originated the role of Eddie on Broadway, and you're back for this tour playing the role again. What kinds of things came back to you automatically and what did you have to re-learn for the tour?

CG: The song "I Could Be That Guy" came back to me instantly. I had to relearn the script and blocking. However, it was fun; I approached the show with a fresh perspective.

BWW: What are your favorite and least favorite parts of touring with a production? How does it compare to performing a role on Broadway?

CG: My favorite thing about touring is that we get to go to a new city every week. So, I get to explore restaurants go sightseeing and learn new things about cities I may not have been to otherwise.

My least favorite thing about touring is that we go to new city every week. LOL! We travel on Mondays and perform 8 shows, Tuesday thru Sunday. So there are no days off.

BWW: I read that Whoopi Goldberg was at your audition for Eddie on Broadway (for those who aren't aware, Whoopi Goldberg played Deloris in the 1992 movie that Sister Act: The Musical is based on). She was also a producer of the show. What was it like working with her?

CG: I love Whoopi! She's is the truth, plain and simple. She was honest with the company, encouraged us and always gave us the BEST desserts! She even tweeted me. Does it get any better than that?

BWW: You've received recognition and awards for several of your roles, including your portrayal of Jimmy Early in the tour of Dreamgirls. Which do you consider your greatest achievement or recognition?

CG: The best is yet to come. I've always wanted one of each. A Grammy, Tony and Oscar. I have much work to do.

BWW: You are a recording artist, as well as an actor. Tell our readers about your music.

CG: I've been recording music under the artist name CHΞSS. I'm releasing a project called ECLIPSE in a few weeks. More info is at

BWW: I love to ask all my interviewees this question: If you could perform (act and/or sing) with anyone, living or not, who would it be? What would you perform?

CG: I would have loved to perform with Sammy Davis Jr. Doesn't matter what show. I would treat the experience as a master class in excellence.

BWW: This week Sister Act: The Musical is in Music City. Share what our readers can expect when they come to see the show... in ten words or less.

CG: Lots of laughter and lots of SHINE!

I'd like to thank Chester Gregory, again, for his time. You can also find him on Twitter @ChesterGregory. Catch Sister Act: The Musical on stage at Tennessee Performing Arts Center in Nashville through March 16th. You can purchase tickets on their website or by calling the box office at 1-877-216-7540.

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Cara Richardson Cara Richardson is an avid theatre fanatic that grew up on movie musicals and showtunes. Participation onstage and off through high school and her first trip to New York City lit her theater fire, but now she prefers to hang out in the audience rather than backstage. She seeks out any chance to see live theatre.


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