Chester Gregory has that ability of the truly talented to repeatedly eclipse his own success. The award-winning stage actor has appeared in some of the biggest theater productions, including "The Jackie Wilson Story," "Tarzan" and "Hairspray," just to name a few. But it was his work in "Dreamgirls" during its national tour that led him back to Broadway as officer Eddie Souther in "Sister Act."
"A year ago when I was doing 'Dreamgirls,' I came back and did several auditions for Jerry Zaks, Whoopi Goldberg and all of those people. And after four auditions, by December when 'Dreamgirls' ended, is when I landed 'Sister Act,'" he recently explained to The Huffington Post. "And then from there, in January we did a reading, then in February we did a rehearsal, and it just took off after that." Opening curtain rose on April 20.
Gregory, a Gary, Ind., native, said that his "Sister Act" role is a bit different from his previous efforts. "This is opposite of a lot of roles that I played. I've done a lot of '60s stuff, a lot of extroverts and exciting characters," he said. "Jimmy Early, Jackie Wilson, Seaweed and all those people. But this character, he's more reserved and more shy. So people get a chance to see a different side of me, and they often tell me when they come to the show, they're like, 'I was just waiting on you to cut up. But you showed us a different side.' So in this role I get a chance to show a lot of control and restraint."
Not only does Gregory's talent on stage engage theatergoers; he also has a knack for the recording booth. In 2008, he released his debut album, "In Search of High Love," baring his soul over 16 smooth R&B tracks. Three years later, he's still determined to make his imprint on the music industry and has a new project in the works.
"I've actually been recording all summer, working on a new sound. What I'm going to do before the end of this year is release a new song. It's actually a remake of a Jackie Wilson song called 'To Be Loved,'" Gregory revealed. "Earlier this year I thought that I was going to have the opportunity to go to the Black Ensemble [Theater] and do 'The Jackie Wilson Story,' but that's not happening because I'm staying with 'Sister Act' and fulfilling my contract with that show. But I still recorded this song, so I'm going to give the song out. That will be for this year, and then at the top of next year I'll have a whole new [as-yet-untitled] project."
In addition to balancing a career between music and theater, the Broadway star and Apple enthusiast is set to enter the mobile app business with the release of "UnWord." Gregory decided to give the endeavor a shot after a close friend approached him with a concept. "A friend of mine and entrepreneur, Ryan Glen, hit me up early last year, and he said, 'I have an idea for an app.' So we started talking about it, and as the app started coming more into development, I started giving him more ideas that I had about the game," Gregory explained. "It's called 'UnWord,' and 'UnWord' is a game where you're offered a word, and then the word itself makes a custom keypad at the bottom of the screen. And then from that word, you have 60 seconds to see how many words you can come up with inside that word. So you're kind of decoding the word and rewording the word and seeing how many you can get."
"I sort of thought about trying the app business before, but I didn't have the initiative to do it on my own," he added. "I think it's a very lucrative business, and it's an opportunity for people to be as creative as they want to. You're really just limited to your imagination and your budget."
As for any plans to develop additional apps, Gregory is already thinking about the possibilities for combining his love of many arts into one simple application.
"I have a lot of thoughts for apps right now. I'm going to try to develop some new ideas for games and stuff like that," he said. "So I definitely see that happening in the future. As soon as I get this first one out and see how it does, I definitely want to do things that tie into Broadway and tie into music."
"UnWord" will be available on Oct. 16 via the iTunes app store or at UnWordGame.com.