Chester Gregory to perform again in Chicago

2013-03-18T00:00:00Z 2014-04-13T15:53:05Z Chester Gregory to perform again in ChicagoEloise Marie Valadez, (219) 933-3365

Gary native Chester Gregory will be lighting up two Windy City stages this week.

Gregory will perform as a special guest at "Book of Mormon" actress Syesha Mercado's concert tonight at City Winery in Chicago and then take the stage at 7:30 p.m. March 24 for a one-night only performance of "The Eve of Jackie Wilson" at Chicago's Black Ensemble Theater.

The singer/actor earned a Jeff award and gained critical praise for his role as Jackie Wilson in "The Jackie Wilson Story," written by Jackie Taylor, founder of Black Ensemble Theater. It debuted in 2000 and  later Gregory toured with the production.

"It's been about 10 years since I really performed in Chicago," said Gregory, during a recent telephone interview. He's been busy throughout the last decade performing roles in Broadway and touring shows such as "Sister Act," "Hairspray," "Shrek," Dreamgirls," and "Tarzan."

"I love coming home," he said, adding he visits the area about twice a year. "Coming back home is a way to stay grounded and connected to my roots. I still have the same friends I had when I was growing up."

Gregory said he's thrilled to bring "The Eve of Jackie Wilson" to The Black Ensemble Theater. He wrote the show which takes a "look at Wilson's life the day before he collapsed." He's also looking forward to the City Winery performance tonight with his good friend Syesha Mercado, a former finalist on "American Idol."

"I'll be singing a duet with Syesha," he said. "I'm happy to come back and honored that people have been so loyal and supportive of my career all this time."

A singer with an eight-octave voice, Gregory currently also performs as Chess in the musical arena. He said he was influenced by stellar singers such as Jackie Wilson, Otis Redding, James Brown and his all-time favorite Michael Jackson, whom he had the opportunity to perform for in 2003 when Jackson visited Gary.

"Michael Jackson was so influential in my career. He changed the face of pop culture," he said.

Gregory said he admires the work of Black Ensemble Theater founder Jackie Taylor and is thankful for the opportunity to again shine the spotlight on icon Wilson when he performs the one-man show at BET.

"Jackie Taylor is a visionary," he said. Gregory said he admires her creativity, talents as a performer, writer, producer and director and her business sense.

"She's living proof of whatever you set your mind to you can do it and it is achievable," he said of the woman who grew up in Chicago's Cabrini Green.

Gregory, a graduate of Emerson School of Visual and Performing Arts in Gary, earned a bachelor of fine arts degree from Columbia College Chicago.

Tickets for tonight's City Winery performance are $15. For more information about the show, visit Tickets for "The Eve of Jackie Wilson," at 7:30 p.m. March 24 at Black Ensemble Theater are $45. For more information, call (773) 769-4451 or visit More info on Gregory can be found at

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