In 1995, a young kid from Gary showed up at the Black Ensemble Theater in Chicago to audition for an all-black version of “A Streetcar Named Desire.” Although neither Stanley Kowalski nor the rest of Tennessee Williams’ characters are exactly known for their musical prowess, Chester Gregory II came out singing.
He didn’t get a part. But he made an indelible impression on the woman who was playing Blanche DuBois.
“I told him that we would one day build a show around him,” said Jackie Taylor, the indefatigable founder and artistic director of the Black Ensemble Theater. “I told him I was going to tour the show, and that when it reached New York, they were going to pick him up.”
Taylor did indeed build a show around Gregory: “The Jackie Wilson Story (My Heart is Crying, Crying).” It did indeed tour — its stops included the legendary Apollo Theater in Harlem. And when Gregory reached New York, they did indeed pick him up. And they’ve kept him.
Like most rides in show business, Gregory’s trajectory has had some severe bumps. But everything Taylor told him has come true.
He became a Broadway name and Black Ensemble’s biggest breakout star. This week, Gregory comes home to Chicago with Robert Longbottom’s new touring production of “Dreamgirls.” The 1981Motown musical by Henry Krieger and Tom Eyen has a two-week stand beginning Tuesday at the Cadillac Palace Theatre.
Gregory (who has dropped the “II” from his billing) is playing James “Thunder” Early, a character based on James Brown. But he well knows he owes his career to two intertwined Jackies: Taylor and Wilson.
“Jackie Taylor is my theater mother,” Gregory said in a telephone interview from the road. “And ‘Jackie Wilson’ taught me how to perform.”
By 1997, Gregory had graduated from Columbia College and was appearing in a revue called “Chicago’s Golden Soul,” a Taylor production designed to showcase the music of such homegrown artists as Curtis Mayfield, Gene Chandler and Jerry Butler. Gregory’s falsetto on Chandler’s “Duke of Earl” and Mayfield’s “Rainbow” pierced the air.
Mother Taylor hatched an idea.
“I had been wanting to produce the Jackie Wilson story for a long time,” Taylor recalled. “But I always felt like I didn’t have a strong enough Wilson. This was going to be a ride specifically for Chester.”
Taylor’s “The Jackie Wilson Story” opened at the end of February 2000. Gregory was a sensation in the title role.
It wasn’t so much how he wailed his way through a plethora of Wilson hits, from “Reet Petite” to “A Woman, A Lover, A Friend” to “(Your Love Keeps Lifting Me) Higher and Higher.” It was the fearless way he re-created Wilson’s famously athletic on-stage moves. Gregory could jump down from a piece of furniture and land in the middle of the splits. And — most eye-popping of all — he could re-create the famous backwards flip that Wilson performed onstage.
“A lot of the time, I didn’t even have an understudy,” Gregory said. “I had to learn how to give my all in every show.”
It was the best show Black Ensemble had ever produced. And it belonged to Gregory. It was such a hit that it played most of the year on Chicago’s North Side.
By 2003, Black Ensemble had found a commercial partner and taken the show on the road –to Baltimore, Richmond, Louisville and Harlem. Just before the tour began, the expanded version of the show was staged on Chicago’s South Side at the New Regal Theatre. Melba Moore was added to the cast. Seemingly under-budgeted for a Broadway-style musical, the show at the New Regal was much clunkier than at its original, more intimate and incendiary staging. But Gregory was just as good.
At the Apollo, the show got mixed-to-negative reviews. But Gregory was hailed as a star.
“There is essentially one reason — and it’s a very good one — to see “The Jackie Wilson Story,” and that is the star, Chester Gregory II,” began Bruce Weber’s New York Times review. “To call a performer unique is generally to be cliched and hyperbolic, not to mention wrong, but Mr. Gregory puts on a show of such physical and vocal dexterity that it’s almost impossible to imagine that anyone else could do it.”
But not all the Broadway casting agents found their way to the Apollo. The reviews had hardly been raves. A few weeks later, Gregory found himself performing at a benefit for the Manhattan Theatre Club. Marc Shaiman and Scott Whitman, the creators of the Broadway hit “Hairspray,” happened to be in the audience.
“Scott and I were like, ‘Who the … is that,” Shaiman recalled this week. “Since we were about to need a new Seaweed in ‘Hairspray’ on Broadway, we immediately called our casting agent Bernie Telsey and said, ‘Sign him up.’ Honestly, I don’t even remember his audition, if he did one later on; he was so incredible that night that the part was his before he left the stage.”
Gregory did Seaweed for the next 2 1/2 years. That meant he had to move to New York, although his then-wife, the busy Chicago actress Kimberly Hebert Gregory, initially stayed in Chicago.
Before long, the couple found themselves pulled in different directions. Hebert Gregory is now a New York actress of some repute — she recently starred in a widely acclaimed production of “The Brother/Sister Plays” at the New York Public Theatre, but the couple (who have a 10-year-old son) have divorced. “We have been able to maintain our friendship,” Chester Gregory said.
That stand in “Hairspray” has been Gregory’s only Broadway hit so far. But he has worked steadily since in major new musicals.
From “Hairspray,” Gregory landed the role of Turk in the critically maligned Disney musical “Tarzan,” which still managed to run from May 2006 to July 2007. He then appeared as Dupree in the musical version of John Waters’ “Cry-Baby.” That show also was mauled by the critics and only lasted for 68 regular performances.
Then Gregory got what looked like his big break — the role of Donkey in “Shrek: The Musical,” the theatrical version of the part first voiced by Eddie Murphy. It did not go well. Wilson was replaced before the show made it to New York. Everybody else stayed in the show.
“I still don’t fully know what happened,” Gregory says. “I made some suggestions about the role, which they took. But they decided to go in another direction with another actor. I was under contract with Dreamworks, and they fulfilled all their obligations to me. It was cool.” But as with every time before, Gregory has immediately found more work. “I’ve always tried,” he said, “to take each experience and learn from it and become a better person.”
This particular production of “Dreamgirls,” which stars Moya Angela as Effie White, alongside Syesha Mercado as Deena Jones, Adrienne Warren as Lorrell Robinson and Margaret Hoffman as Michelle Morris, began at the Apollo Theater last fall, where it got mostly enthusiastic notices. There is some talk of a full-on Broadway opening following the tour, which includes a month in Tokyo. Aptly enough, the fictionalized trio in the show itself begin and end their careers at the Apollo, a key venue in the Gregory story.
Still, Black Ensemble trumps the Apollo in the Gregory deck. In fall 2011, Taylor expects to open the new Black Ensemble Theater on Chicago’s North Side. Taylor said she wants the opening production in the new complex to be a reprise of the company’s greatest-ever hit, “The Jackie Wilson Story,” starring the man who created the title role and built himself a career. Gregory says he owes her that much.
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cjones5@tribune.com
