BY lUCIA MAURO
 |
It’s a Wednesday afternoon, and Chester M. Gregory II is changing into a black silk shirt while combing his dark curls into an artful pompadour. A pair of shiny two-tone shoes and a long red jacket are neatly arranged in the backstage area of Black Ensemble Theatre’s space in the Uptown Center Hull House. While Gregory softly shares stories about his early interest in theatre, his fellow artists do their warm ups and put the finishing touches on their costumes and makeup.
In a few minutes, Gregory will explode onto the stage performing the title song from The Jackie Wilson Story (My Heart Is Crying, Crying) for a crowd of visitors from Know Chicago, a local social-educational tour organization, whose members were being treated to a 30-minute revue of Black Ensemble Theatre’s greatest hits. His four-octave range, sky-high splits and glowing charisma bring down the house. And, for a moment, I feel like the larger-than-life, show-stopping Gregory and the understated young man I had been chatting with backstage are separate people.
"I’m really shy by nature," acknowledges the star of one of BET’s longest running shows, "but, as soon as I’m on the stage, it’s like pow!"
Gregory landed the role of Jackie Wilson—a role many people say he was born to play—in 1999. The musical revue, penned by BET’s artistic director Jackie Taylor and music director Jimmy Tillman, salutes the famous Detroit-born R&B vocalist and one of the first great soul singers whose career spanned the 1950s through the early 1970s. The Jackie Wilson Story, which earned Gregory a 2000 Jeff Award, ran until this summer. The show was scheduled to embark on a national fall tour. In the aftermath of the terrorist attacks, the tour was cancelled but will resume next year.
Meanwhile, BET has brought The Jackie Wilson Story back for a limited engagement in its Uptown space through Jan. 6—with Gregory rekindling the contagious charm and vocal-dance pyrotechnics of this legendary African-American performing artist.
"When the show opened," recalls Gregory, 28, "I was nervous. People have such high expectations of Jackie Wilson. He paved the way for Michael Jackson and Prince. But I got so much help from Jackie Taylor, who continued to revise the script during rehearsals and customize it to each performer’s individual strengths, and from Jimmy Tillman, who encouraged me to improvise and master Jackie Wilson’s mannerisms."
Gregory also viewed videotapes of Wilson and immersed himself in his recordings to capture the performer’s every nuance. Over the past two years of transforming himself into one of the greatest show men of all time, Gregory believes he has become a better entertainer.
Entertainment, however, has been part of Gregory’s life ever since his mother took him to see musicals (Peter Pan, The Wiz, Annie) from an early age. His parents would then buy the soundtracks from these classic shows, and the young Gregory would sing along to them—typically in private.
"I wasn’t dancing or singing in the hallway," he clarifies with a laugh. "I would practice singing and dancing in the basement before my parents got home from work. Then I would enter a talent contest or be in a production at school, and I would just shock everybody the day of the show."
Gregory grew up in Gary, Indiana. He was inspired by the music of Michael Jackson, Sammy Davis, Jr., Stevie Wonder and Sarah Vaughn. In fact, he wowed family and friends when he recreated Michael Jackson’s "Thriller" video live at the tender age of ten.
"I was the last person you would choose for basketball," he says. "I knew that I wanted to go into theatre ever since I was in grammar school. My parents were very supportive and exposed me to the arts at an early age. My mother is a teacher, and she would ask me to come into her school and help choreograph routines or write a poem for one of the shows."
Plus he was involved with plays his mother directed for teen awareness programs in his hometown. Yet Gregory, an only child, says he still felt "like an oddball"—a challenge he met by believing in his dream and not letting the fact that he was different deter him. He says that, at various points in his life, people have told him he couldn’t sing, dance or act.
Nevertheless, in addition to receiving private vocal training from the age of 14 and performing in countless talent shows and with theatre companies in Indiana, Gregory continued to pursue a theatrical career. He was accepted into the Emerson School for the Visual and Performing Arts in Gary. After graduating and chalking up more performing experience, he enrolled in Columbia College Chicago, where he received his BA in musical theatre in 1995. Musical theatre was his top choice because of its "triple-threat" nature.
But Gregory was never one to plunge into extravagant productions or make his star power immediately known. He says that during his freshman year at Emerson, he stayed in the background—waiting until his junior year to move into more prominent roles (like Judas in a school production of Jesus Christ Superstar.) This pattern continued at Columbia.
"Each time I started a new school," says Gregory, "I would start out shy. I would take my time, observe and feel things out. It wasn’t until later on that I would open up."
One of the pivotal theatre moments of his life was being cast as Jesus in Columbia’s staging of Jesus Christ Superstar.
"At that time," he recounts, "I was into writing songs, and I was directing the gospel choir. When I was given the chance to play Jesus, I felt it was such a strong role that affirmed I was moving in the right direction."
His parents’ encouragement remained steady.
"My parents always went to the shows I was in," adds Gregory, who now lives in Chicago. "My father would pick me up from rehearsals at Columbia at midnight; then he would get up at five in the morning to work in the mills."
During a follow-up telephone interview, Gregory continues his story while preparing breakfast for his two-year-old son, Chester III. While a senior at Columbia, Gregory auditioned for the Black Ensemble Theatre but did not get cast. Then, one year later, he was called in to replace an actor in Doo Wop Shoo Bop in which he played Frankie Lymon.
Previously, he had landed his first professional theatre role in The Train Is Comin’ at Chicago Theatre Company.
But, like most actors right out of college, Gregory could not make a living in the theatre. He got a job as an activities coordinator for a daycare center in Merrillville, Indiana, where he involved the youngsters in theatre. He then worked as the auditorium manager at a high school in East Chicago, Indiana for four years. While there, he founded a drama club and created a successful theatre program. Today, Gregory devotes himself full-time to his theatrical career and is affiliated with Gallery 37 Center for the Arts.
Closely associated with Black Ensemble Theatre, Gregory also has starred as the Duke of Earl in Chicago’s Golden Soul and as various characters in The Otis Redding Story. He is especially drawn to BET’s robust involvement of the audience. "We can really interact with and respond to the audience," adds Gregory. In addition, he has performed in Memory Lane and Bingo Long at Dream Street Theatre.
Jackie Wilson has been a dream role for Gregory. But he is aware of being typecast. "That’s why I need to step away from the role for a while," he says. "I want audiences to see me in a range of roles."
After The Jackie Wilson Story closes, Gregory can be seen in Regina Taylor’s Drowning Crow (a story about African-American artists inspired by Anton Chekhov’s The Seagull), opening Jan. 14 at the Goodman Theatre. He will then headline the Jackie Wilson tour later in February.
Gregory now has a music project in the works. He just finished recording his own CD for which he wrote a mid-tempo inspirational song, "Marching On," in memory of the victims of the Sept. 11 tragedy. The CD includes 13 contemporary songs, and Gregory is looking for a distributor. He plans to shoot a music video for one of the songs. Plus he has been auditioning for both theatre and film.
The actor-vocalist is most fervently drawn to live performance.
"There’s nothin’ like it," says Gregory of the stage. "In theatre, there’s no take two. You absolutely have to make it work. Sometimes when I perform, I approach it as if it were my last performance. I give it my all. And I try to be as honest as I can."
Gregory recalls being put in touch with the heart of theatre this past summer. The power went out during a performance of The Jackie Wilson Story. Someone wheeled in a piano, and they continued the show with no lights or high-tech sound equipment.
"I believe that was one of our best shows," says Gregory. "It caused the audience to really get involved. And it pared theatre down to its essence."
Viewing theatre as "a humbling experience," Gregory feels that offering advice to aspiring actors would sound a bit pretentious. Instead he passes along an uplifting message: "If you know that what you’re doing is right and believe it with all your heart, then don’t let anything hold you back."