Artist: Chester Gregory
Interviewer: Tamara Ashley McCullough

From the modest steel mill town of Gary, Indiana to the bright lights and opulence of Broadway, singer/songwriter/performer Chester Gregory has taken the whirlwind journey from the heart of the Midwest to the top of the Big Apple with several stops along the way. Passion, dedication and hard work have paved the road for this award-winning performer.

His love for performing began when he was a child with his mother taking him to the theater. He would eventually perform himself, so Gregory’s mom would show tough love with her honesty. “If it sucked, she would tell me it was horrible. It was cool; she was just honest,” Gregory said. He was immediately bitten by the acting bug where he loved the rush he received. “It’s the adrenaline rush, the audience response.” Gregory’s singing career took off from the incredulity of a teacher. “One day my music teacher did a double-take because of my singing. It’s my love of music, my love of the arts.” Gregory admitted that he was always the oddball in the family who wanted to be an artist and could never imagine working a regular, 9-5 job. He explored his interests by attending both a performing arts high school and college. His theatre odyssey began with him touring with the Chicago Theatre Company followed by the Black Ensemble which produces autobiographical shows. This is where Gregory debuted in New York at the Apollo Theatre by landing the lead in “The Jackie Wilson Show,” which ran off and on for three years. From there, it was the critical success, “Hairspray,” which ran on Broadway. “Dreamgirls,” though another success for Gregory, didn’t make its way to Broadway. “There was some disappointment; it would’ve been a chance to win more awards and have lots of hard work recognized.” Though Gregory has been nominated and won his share of awards, has was unaware of the existence of one. “I was excited about the nomination but had never heard of [one of] the awards. I first found out from a text and was like, ‘What?’ To win was very important.” While appreciative of the awards, he knows where to draw the line between life and work. “It has nothing to do with me personally; the awards are for work. It feels great to be appreciated, but it doesn’t define me.” Through a hectic performing schedule, Gregory still finds time for his music where he released his debut album, “In Search of Love.”

“Lots of people were surprised by the integrity of the music which they said didn’t sound all show business.” Through his music, Gregory is able to accomplish something that he can’t while acting. “Doing music allows me to tell my story, share my reality; where an actor is telling somebody else’s story. Music is life to me.” When creating his music, Greg uses a simplistic routine. “I just need a nice, warm space about 80 degrees and Smart Water and I’ll be good.” Despite the favorable comparisons Gregory has received to several, top artists, he has not let it get to his head by reflecting on his role model’s approach. "I don’t let it affect me, having always looked up to Michael Jackson. He was humble; that’s always stood out to me.” Gregory relayed an anecdote to further drive his point home. “I remember the ‘Superman’ movie where Superman was trying to rush in a crowd as Clark Kent, but he was polite. He had all the superpowers and could’ve pushed people but didn’t; he was respectful.”

Gregory doesn’t like to self-compare himself to other artists; he leaves that to the fans. He thinks that’s a difficult question for any artist. “The audience members decide; I’ll just be myself. It depends on what I’m doing vocally---I’m a vocal chameleon since I have a few different voices.” Daily, Gregory keeps a fast-paced life which is never “typical.” “Just last month, I moved into an apartment, shot a video and was in the studio. Life goes on daily. Just depends on what I need to accomplish.” He recently found out that he will be in the play, “Sister Act.” “My schedule will be regulated then. It will be 8 shows a week with a 10-6 rehearsal schedule at first and then closer to the show a 12 to midnight schedule.” Despite his frenzied life, Gregory is always looking toward the future. “By the end of this year, I hope to have 3 videos in rotation, increase my fan base by 100,000 and sometime in the future a Tony nomination. And my new album out by late spring, early summer. At the end of the day, Gregory wants to leave his fans with inspiration. “People want to be entertained and I hope people will be inspired, be a better person.”