By Ben Joravsky

It’s about an hour before curtain, and Chester Gregory’s got a cold. Nothing too serious, really, nothing as bad as the stomach flu that had him bent over the toilet minutes before one show several weeks ago.

It’s just that his throat’s sore and his nose is stuffed and his energy’s running low.

“Forty-five minutes,” says the theater’s technical manager, a woman who goes by the name Razor, as she bustles through the backstage dressing room.

No matter how much he’d like to, he can’t go back to bed, he can’t miss this Sunday matinee. He’s the star of Black Ensemble Theater’s Jackie Wilson Story (My Heart Is Crying, Crying…). It’s been on an open-ended, sold-out run at the Uptown Center Hull House since last February–and the audience, mainly black women young and old, is coming to scream, cheer, and cry over him.

“Thirty minutes,” says Razor.

Gregory rifles through his shoulder bag and takes out lozenges, Gatorade, and throat spray. Evelyn Danner, the assistant stage manager, calls him to a stool in the corner. He takes a seat and she slathers gel on his scalp.

From just beyond the dressing room he can hear the faint murmurs of the patrons as they take their seats. A horn player wanders by, gently blowing his trumpet. Lyle Miller, an actor in the ensemble, darts in, cheeks still chilled from the outside cold. Rolando Boyce, another actor, quietly irons his pants. The dressing room radio’s tuned to Herb Kent’s dusties show. Sam Cooke’s singing “Cupid.” Miller softly sings along.

Jackie Taylor, the show’s writer, director, and producer, walks through the dressing room and pats Gregory on the shoulder. “Good house out there,” she says.

He nods.

“Ready?” Danner asks him.

“Just a second,” he says. He pops a lozenge, swigs some Gatorade, and sprays his throat. “OK,” he says.

Brush in hand, Danner starts to comb Gregory’s short Afro into a 50s-style pompadour as his slow but steady transformation into Jackie Wilson begins.

The last thing Gregory would have imagined as a boy growing up in Gary was that his path to fortune and fame would lead him to Jackie Wilson–or any 50s or 60s R & B singer, for that matter. Born Chester Gregory Jr. on December 10, 1972, he wasn’t the kind of kid who listened to his parents’ old records. He was very much a child of his time. His music was rap, hip-hop, and contemporary R & B–with one big exception.

“If you grow up in Gary, you’ll hear a lot about Michael Jackson, ’cause that’s where he’s from,” says Gregory. “He was a major influence on me–‘Thriller,’ ‘Beat It,’ and ‘Billie Jean.’ I listened to all of that stuff. And I heard his earlier material–the things he did before I was born–because I watched the Jacksons’ cartoon on TV.”

Gary, of course, is a very poor city, and the 1980s were unusually hard times. But Gregory, an only child, wasn’t deprived. His parents are still working, his father in a steel mill, his mother as a third-grade teacher in the East Chicago public schools. Gregory showed his talents at an early age and was encouraged to sing, dance, and perform. “There were a lot of good dancers in our day, but my man Chester was the best,” says hip-hop writer Kevynn Bunkley, who was one of Gregory’s closest childhood friends. “Back in those days we’d be doing hip-hop and deejaying shows and just hanging out. We loved kung fu movies. Chester was into Jackie Chan. Me, Chester, and my twin brother Keath formed a dance group called the Tribe. It was b-dancing, you know, break dancing. Chester was the star.”

To no one’s surprise, he attended Emerson High School for the Visual and Performing Arts. “It’s a public school–Gary’s so-called Fame school, like in the movie,” says Gregory. “You had to audition to get in.”

“He was the best dancer in the school–nimble, quick, and versatile,” says Bunkley. “Chester could do it all, moon walk, splits, break-dance. He was very popular–everyone wanted him to come to their parties.”

He was a favorite of the teachers, who awarded him the lead in The Pajama Game his senior year. He also played Judas in Jesus Christ Superstar.

“If you asked me back then, I’d have told you that I was going to be a singer and a dancer somewhere, either on Broadway or Hollywood,” says Gregory. “I just didn’t know how it would happen.”

Reality hit home in 1991, when he enrolled at Columbia College. He was living in Gary and taking the train each day to Chicago, where he discovered that as good as he’d been in high school, he was just one of many talented performers in college. At first he retreated a bit. “He struck me as being very young and very shy–but, my gosh, such a pleasant fellow, a real sweetheart,” recalls Stephanie Shaw, a theater professor at Columbia. “His strength was his voice. From the start, the voice was there. It took time to develop everything else.”

As a senior he won the title role in Jesus Christ Superstar.

“He was a little stiff at first onstage and it took a little goading, or hand-holding, to get him to really open up in rehearsals,” says Shaw. “But after a while he took to it. He knew what he had to do. He really responded to the audience and the moment and allowed it to happen.”

Ironically, winning the lead worked against him in that he lost a chance to showcase his dancing skills. “You have to realize that even though the show’s named for him, Jesus doesn’t do a whole lot of moving,” says Shaw. “He just stalks around a lot and looks disagreeable. He doesn’t dance–people dance around Jesus.

“But still, with Chester you could see he had enormous potential. It was just a question of when it would take off. You never really know the answer to that question. You don’t even know for certain that it will take off.”

In 1995 he graduated from Columbia and auditioned for his first professional show, Black Ensemble’s Streetcar Named Desire.

“A lot of people at Columbia were encouraging me to try out for plays so I just decided the time had come to do it,” he recalls. “I went down to the auditions with Sophia, Sophia Perkins–she plays my mother in the Jackie Wilson show, by the way, but back then she was also going to Columbia. Anyway, Sophia encouraged me to do everything in the tryout–to do a monologue and a song. So I sang a song from Jesus Christ, ‘Gethsemane.’ I’m screaming it out, and Jackie [Taylor] is just sitting there. I think it kind of shocked her. I remember people looking at me as if they were wondering, you know, ‘Why’s he doing all this singing?'”

Taylor didn’t cast him–“I failed the audition,” Gregory jokes. But she didn’t forget him either. Taylor says she realized right away that he was ideal for her musical docudramas about famous African-American entertainers. “I could see Chester had talent, but he was so inexperienced as an actor,” says Taylor. “That doesn’t bother me so much, because I can teach folks to act. The kind of singing and dancing talent he has–you can’t teach that.”

Almost from the day he graduated from college, Gregory’s been performing somewhere in Chicago. In 1995 he played in the Chicago Theatre Company’s Train Is Comin’. He was just finishing that run when Taylor called to say an actor had left her hit show Doo Wop Shoo Bop.

“They needed a replacement, and I got the job,” he says. “It was my first show for Jackie.” After that he became a regular, as Taylor cast him in The Otis Redding Story, Sweet Soul Music, and Chicago’s Golden Soul.

In each of these productions, Gregory sang the group numbers and took the spotlight for a solo or two. He soloed with songs by Gene Chandler (“Duke of Earl”), Arthur Conley (“Sweet Soul Music”), Sam & Dave (“Soul Man”), and, coincidentally, Jackie Wilson (“Higher and Higher”). With each song he crossed a generational gulf, mastering tunes most of his audience knew intimately. “It doesn’t really matter if the actors are unfamiliar with the music,” says Taylor. “I don’t expect young actors to know the music of my generation. I give them tapes to listen to and videos to watch. They can learn. It may be your music, but to them it’s just an actor doing a role. They study and portray it.”

These roles earned him a few favorable lines in reviews, but not as much money as he needed. By 1998 he was married. A year later, he and his wife had a baby boy (Chester Gregory III). To make ends meet, Gregory taught theater and dance at East Chicago Central High School. “I’ve been fortunate because I’ve been in a show pretty much from 1996 on,” he says. “With each show I felt I was getting better. People were starting to recognize me a little bit. I did Gene Chandler in Chicago’s Golden Soul. One night, Gene Chandler came to the show. He cried when he saw me sing ‘Duke of Earl.’ He said I did it right.”

After Golden Soul closed in 1999 Taylor came to Gregory with a proposition. She wanted him to audition for the lead in a new play based on the life and music of Sam Cooke. “I was really excited about that,” he says. “It was a challenge because I’ve always relied on my dancing in a show. But Sam Cooke wasn’t known for his dancing, so I figured it would make me concentrate on the singing. I showed up for the audition all set to do ‘A Change Is Gonna Come’ or ‘You Send Me.'”

But Taylor announced that she had changed her mind. The next show wasn’t going to be about Sam Cooke, it was going to be about Cooke’s friend and rival, Jackie Wilson. “I was kind of disappointed,” says Gregory. “I had already played Jackie Wilson, at least for one song. And I didn’t want to keep playing the same people over and over. I wanted to show what else I could do. I almost went home, skipping the audition. But how can you say no to Jackie? She said, ‘Do you need a minute to get ready?'”

He stepped offstage for a moment to gather himself and returned to sing “Doggin’ Around,” a song he knew from Doo Wop Shoo Bop. “I didn’t do anything fancy in it, like a split, but I tried to give it some suggestion of Jackie Wilson’s style,” he says.

Jackie Taylor showed no reaction. “I thought I’d done all right, but you never really know what the director’s thinking,” says Gregory. But his audition had only convinced her she’d been right in the first place. “I always knew Chester was going to play Jackie Wilson, though I didn’t tell him that,” says Taylor. “He had it all–the looks, the charisma, the voice, the sexuality. Plus, he could dance. To do Jackie Wilson, you have to be able to dance.”

Taylor had her own brush with stardom. An actress who grew up in Cabrini-Green, she played Johnny Mae in Cooley High, a 1975 coming-of-age flick about black teenagers in Chicago. The offers she received afterward were demeaning, she says, so she got out of acting and created Black Ensemble Theater. Over the years she’s built a loyal following by writing, directing, and producing shows that feature music her audience loves.

Jackie Wilson’s story fits the package so well it’s remarkable she didn’t stage it years ago. From the mid-50s to the early 60s, Wilson was a big man in R & B. He sold out concerts and cranked out hits–“Lonely Teardrops,” “Doggin’ Around,” and “(Your Love Keeps Lifting Me) Higher and Higher,” to name but a few. His style and talent were peerless. He tore into his songs, electrifying fans with splits and shimmies. Elvis Presley said he learned moves from watching Wilson perform; Mick Jagger, Rod Stewart, and all the other white 60s rockers owe him.

But Wilson was self-destructive, as much victimizer as victim. He scorned the overtures of black producers (Motown’s founder Berry Gordy, no less) who might have helped him, only to be deceived by the white manager he naively trusted. He couldn’t (or wouldn’t) curb his indulgences. He cheated on his wife, disregarded his children, drank too much, wasted his money, fell into debt, and signed away the rights to his songs. (“It seems the more records he sold, the less money he made,” as one character in the play puts it.)

In 1975 he had a stroke while performing in a Dick Clark oldies show in New Jersey. For more than eight years he drifted in and out of a coma while various friends, ex-wives, and lovers battled in court for control of the remaining scraps of an estate he had mostly squandered. He died in 1984 at age 49.

Fifteen minutes before curtain, Evelyn Danner finishes combing Gregory’s hair. Gregory stands, stretches, and strips to his shorts. All around him, actors and actresses in the ensemble in various stages of dress are coming in and out.

His first costume of the show–he will go through some 15 changes–is a gold suit. He slips on the trousers, slides into his jacket, fiddles with his rings, and straightens his tie.

“Ten minutes,” says the stage manager.

On the backstage radio, Herb Kent’s tallying the call-in votes in the afternoon battle of the stars. “It’s Marvin Gaye versus Sam Cooke,” Rolando Boyce tells Lyle Miller.

“For real?” says Miller.


“I know who I’m for,” says Miller, who plays Sam Cooke in this production. He pulls a cell phone from his pocket, dials the radio station, and casts a vote for Sam Cooke. “Hey, every vote counts,” he says.

“Five minutes,” calls the stage manager.

The band has taken its place on a platform above the stage. The sounds of the overture–horns, guitars, keyboards, drums–pulse in. The dressing room fills with the cast of 11 young black performers, and Jackie Taylor.

“Circle,” says Taylor.

They gather around her. As if by divine intervention, the radio plays “A Change Is Gonna Come,” Sam Cooke’s haunting hymn about faith and hope.

“Oh, Lord!” Taylor exclaims. The actors form a circle, join hands, and sing with Cooke, their voices rising high above the overture.

I was born by the river in a little tent,

Oh, and just like the river I’ve been

a-runnin’ ever since

It’s been a long, a long time comin’

But I know, a change gonna come–oh yes it will

It’s been too hard livin’, but I’m afraid to die

‘Cause I don’t know what’s up there

beyond the sky

It’s been a long–a long time comin’

But I know a change gonna come–oh yes it will

Taylor turns the radio off and rejoins the circle. They all bow their heads and Sophia Perkins, Gregory’s old college friend, leads the prayer. “Thank you, Jesus,” she says. “Thank you for our strength. Lord, lord, help us to touch the people out there. Lord, I thank you for our gifts and our talents. Lord, God.”

“Amen,” says everyone. They raise their voices in an exuberant exercise, a cascade of notes that culminates in a happy shriek. They clap their hands, embrace, and dash to the wings to prepare for their entrance.

Left behind in the dressing room are Gregory and Miller, who’s making final adjustments to his costume.

The stage manager hisses from outside the room: “Lyle, come on!”

“Oops,” says Miller, and out he runs.

Now Gregory’s alone. He breaks open a bottle of Gatorade and takes a long sip. He sprays his throat, pops two more lozenges. He leans his head against the wall and sighs. He adjusts the rings on his pinkie fingers, brushes the sides of his black-and-white shoes, shifts his shoulders in his jacket. He can hear the ensemble onstage, singing the opening number, a song Taylor wrote that begins: “My heart is crying, crying.”

He walks to the side of the stage, past a hot plate that smells of burned coffee. He slips beneath the band’s platform. The onstage singing is louder. He walks down a dark, narrow corridor behind the set. He stands behind a door that leads to the stage.

“My heart is crying, crying…”

He motions to the stage manager. She takes his cold supplies and places them near the mirror where he’ll be changing costumes between scenes. He bows his head and silently prays. The onstage singing stops. He pushes open the door and bursts into the spotlight. His yellow jacket shimmers and his pinkie rings gleam. He’s got the grin, the cocky little Jackie Wilson grin that says, “I’m good, I’m very good, and I know it.” The crowd cheers. He hits a high note: “Oooh!” He stops, smiles, then launches into “Am I the Man”:

You oughta be here to hold me tight

You oughta be here to treat me right

You oughta be here to hold my hand

And try to make-ah me understand

And, baby, tell me once again, uh-huh,

Am I the man?

Three short steps lead down to the stage. He effortlessly hops to the bottom step, then, just as effortlessly, back to the top. With a look of devilish insouciance, he throws open his arms, kicks back his head, and sings on:

You oughta be here to letta me know

You oughta be here to tella me so

You oughta be here to prove it’s true

That I’m the on-ah-ly one for you,

And, baby, tell me once again,

Am I the man?

The women in the front rows clap in time and sing along.

Chester Gregory, cold and all, has vanished. Jackie Wilson’s taken the stage.

The show was a hit from the start. It has Jimmy Tillman’s rockin’ house band, sizzling dance routines, and the compelling tale of Jackie Wilson’s rise and fall. It’s a parable about fame and fortune, with Wilson as a symbol of every great African-American entertainer who’s wound up destitute.

The play tells Wilson’s story in a series of scenes between the singer and the people around him–his mother, wife, friends, producers. The various characters step into the spotlight on an otherwise darkened stage and narrate increasingly grim details. The show is one of Taylor’s best, but the key to its success–the reason it’s on an extended run–is Gregory’s performance.

Wilson’s offstage life and onstage persona were much the same. He always sought the spotlight, always raced along the edge. He was bombastic and braggy to the point of trash talking fellow performers. “I go on after you ’cause when I’m finished the show is over,” he tells Sam Cooke at one point in the play.

Gregory is shy, almost self-effacing. He speaks slowly and cautiously, and is quick to credit others (particularly his wife Kimberly) for his success. He is, friends say, a variation on a type–the wallflower who comes alive playing a role. “Chester’s so much different than Jackie Wilson,” says Rolando Boyce, who plays several roles in the show. “He’s very generous, he’s always trying to help you out.”

“He’s a perfect gentleman,” adds Opal Staples, who plays Wilson’s forsaken wife. “When we first kiss in the play, he has to grab my butt. In rehearsals he said, ‘I hope this doesn’t make you uncomfortable. I’m just being aggressive ’cause this is my character.’ He didn’t have to say that but he did.”

To prepare for the role, Gregory studied footage of Wilson. “Jackie gave me a tape that’s two and half hours long and I must have watched that tape a thousand times,” he says. “When I do a show the role takes over. I don’t know where it comes from. I don’t know where it goes after the show’s over.”

Some of Gregory’s gestures and movements duplicate things he saw and heard on the video: Wilson’s rooster strut; his boxer shuffle; his yodels, yelps, and shrieks; the way he obsessively fiddled with his collars, cuffs, and rings. Gregory even has a Wilson-like pout that’s really an alluring wink, as when Wilson says to his wife, “Aw, honey, you know I love you.” (This line comes, by the way, soon after he’s left his lover’s bed.) Other moves are more spontaneous, particularly the dance steps that show Gregory’s hip-hop roots. “Jackie lets me improvise a lot,” he says. “To keep the show fresh, I try to vary it a bit. I’m always changing little things here and there. I do that for the people who are seeing it again–I don’t want them to see the same things. And I do it for myself. I don’t want it to become stale.”

The hottest moments are the songs, when he often brings the audience in on the act. “Jackie always tells us to be aware of the audience,” he says. “During rehearsals she moves around the theater, sitting in different seats so that she makes sure we move in such a way that we play to everyone. In a show, I think I’m watching the audience almost as much as they watch me. I usually pick someone out that’s going to, you know, work with me a little.”

Generally, that means flirting with two or three women in the front rows. In “Doggin’ Around” (Wilson’s crocodile-tears lament about his woman’s adulterous ways), he scoots up to one woman, takes out a handkerchief, pats the sweat off his brow, and hands it over. As the crowd whoops, he hands a second sweat-soaked hankie to another fan.

The interaction plays to one of Black Ensemble’s strengths–its audience. They sing along, clap to the beat, talk back to the performers, warn them of trouble ahead–“Don’t do it, Jackie.” When something shocks them, they gasp. “It’s like a church service. You’re not supposed to just sit there in your pews,” says Staples. “I guess the people think that if you’re not going to get into it, why come at all?”

An hour into the show, Gregory’s drunk half his Gatorade. He’s just exited after a scene with Lyle Miller, but there’s one more number before intermission. It’s not just any number–it’s “Lonely Teardrops,” one of Wilson’s biggest hits and another of his classic crocodile-tears specials.

The song, Gregory explains, is relatively simple, just one verse and chorus repeated several times. “But what you do with it is something else,” he says. “If I can get through this…”

He wipes his lips, blows his nose, checks himself in the mirror, walks back to the center-stage entrance, and awaits his cue. The scene is a show within the show, a nightclub act in which Wilson follows Sam Cooke.

A voice announces, “Ladies and gentlemen, Jackie Wilson.” Gregory bounces onstage and bursts into song, backed by a chorus of five actors grouped around two microphones backstage.

My heart is crying crying

Lonely teardrops, my pillow never dries

Lonely teardrops, come home

Come ho-o-o-o-o-ome

Just say you will, say you will (say you will)

Sa-ay you will (say you will)

Hey, hey (say you will)

My heart is crying crying…

Just give me another chance

For our romance

Come on and tell me that one day you’ll retu-u-u-urn

‘Cause every day that you’ve been gone away

You know-a my heart does nothing but burn crying

Lonely teardrops, my pillow never dries…

Instead of fading out, as Wilson does in his hit recording, Gregory, the band, and the backup singers pick it up. Still wailing, he grabs the microphone and shimmies across the stage while the backstage singers repeat Shoo-be-do-wop, wop wow.

Then Gregory stops singing, drops to his knees, and hangs his head, as if too heartbroken to continue.

He looks up at the audience and asks, “Do you know what I’m talkin’ about?”

Someone shouts, “Oh, yeah.”

He drops his head. “No you don’t.”

The crowd laughs.

He leans back so far his head almost touches the stage and he wails in false anguish, “I’m so tired of these lonely teardrops falling down my lonely face while I’m laying my lonely head down on my lonely pillow while I’m in my lonely bed in my lonely room soaking wet.”

The crowd’s on its feet. Women are shrieking.

He sits up and eyes the audience in amazement, as if he’s surprised to see the frenzy he’s created. He says, “I don’t feel good.”

“No,” someone yells back.

“I’ve got the fever.” He repeats the word “fever” again and again, his voice rising higher and higher, until he gasps with exhaustion and falls back, this time so far his head does touch the floor. The background singers keep on singing Shoo-be-do-wop, wop wow.

He lets a moment pass, then slowly looks up at the audience.

“I’m soakin’ wet,” he says.

And he pops the top button off his shirt.

“I’m soakin’ wet.”

And he pops open another button.

“I’m soakin’ wet.”

His shirt’s open to the waist. His chest’s heaving, his abs sweaty and straining.

Six or seven women are hopping in their chairs.

His eyes scan the room, as though he’s searching for someone. The band keeps playing, the background chorus keeps singing, the crowd keeps clapping, he keeps searching. He looks left, then right, then to the center, where in the front row sits a woman he’d given his handkerchief to. He grins and raises his eyebrows. The crowd, sensing what’s coming, starts to laugh. He scoots toward her on his knees, thrusting his pelvis forward with every scoot, until he’s crossed the stage and is at her feet.

He looks up at her suggestively, the pout now more of a leer.

“Uh-oh,” screams the crowd in anticipation.

The woman’s shoulders shake from laughing.

He waits a split second, then says, “Why don’t you come home with me?”

The crowd erupts. “Whooo!”

A woman in the back screams out, “No, me, me, me.”

Another woman’s on her feet waving her arms.

He pays them no attention. His eyes never leave the woman’s face. He takes her hand and slowly brings it close to him, until he’s rubbing it against his chest.

“My heart does nothin’ but burn,” he wails.

The crowd’s standing. He scoots back toward the mike, blowing her kisses as he goes. Her bangs have fallen across her forehead. Her face is rusty red. She’s hugging her girlfriend.

He jumps up from the floor, falls into a split, springs to his feet, then lands on his knees as the lights go dark. The band hits its final note, the first act ends, the audience roars, and he returns to the dressing room and collapses.

Within a few weeks of the opening, word hit the grapevine that this was a show to see. Herb Kent and Richard Pegue started talking it up on their weekend radio shows, and soon the theater’s phones were ringing with ticket orders. In November Gregory won a Jefferson Award for best actor in a musical revue. At the awards ceremony he widened the eyes of the city’s theater establishment with a bring-down-the-house rendition of “Lonely Teardrops.”

“Most of his fans are women,” says Opal Staples. “Matter of fact, it seems like every show has less and less men and more and more women. And they’re getting possessive about Chester too. I’ve had a few women glare at me when we do our kissing, like, ‘She thinks she’s all that.'”

Some women have come back so often the cast knows them on sight. “I’ve seen it three times and I’m going to see it again,” says Barbara Rosario. “I’ve become a groupie, and I’m not really like that. I’ve never been a groupie before. It’s because of Chester. In one show he gave me the handkerchief. He autographed it for me. It says, ‘Thank you, Chester.’ I love it. I keep it in my purse. Oh, he’s so marvelous. He’s so wonderful. He puts so much into it. Oh, Chester, I love you!”

The champion repeater has to be Diane Jones, a retired schoolteacher who lives on the far south side. “I’ve seen it 34 times and that’s still not enough,” she says. “It’s not that easy for me to get here. I take two buses and a train. I take the 87th bus to the Red Line. I take the train north to Broadway and Wilson. I take the 145 to Beacon, and I walk here. I don’t have to worry about taking all those buses back because there’s always some nice young person in the cast who drives me home.”

Jones has become such a fan of the Black Ensemble Theater that she often works for them around the theater as a volunteer. “I’ve seen many other shows here, but this one has broken all the records–I can see it again and again,” says Jones. “But I don’t take comp tickets. No, that would be like taking a ticket from a paid customer. The theater wouldn’t be able to sell that ticket to someone else and they need to sell tickets. I’m delighted to pay because I just love the show.”

For Rosario and Jones and many other women, one of the highlights follows the show, when Jackie Taylor and the cast line up in the lobby to greet the audience as it heads for the exit. They gush over Gregory, hugging him, shaking his hand, posing for pictures with him, and wishing him luck and blessings.

“They like to tell me who I look like–I guess I look like a lot of different people,” he says. “I’ve heard Ken Griffey–you know, the baseball player. And Tiger Woods. I swear, I don’t follow sports so I don’t know half these people. And Prince, lots of people say Prince. And Morris Day. And Nat King Cole. Or someone will say, ‘You look like my son,’ or ‘You look like my nephew.’

“Sometimes you’ll get someone who has a little something critical to say. I had a man tell me, ‘I saw Jackie Wilson and he didn’t do it like that–he did it like this.’ I just nodded. I mean, I watched two and one half hours of Jackie Wilson footage and I never saw him do what that man said he did. But I don’t want to make a big deal about it. I appreciate that the people come to the show. This is after a long performance. Sometimes I’m just drained. I don’t want to be standing around arguing with someone. But mostly everyone is very nice and gracious. They tell me, ‘You’re gonna make it big’–stuff like that.”

As the run continues, the cast has begun to wonder: How long will it last, and what will they do when it ends?

Taylor’s response, virtually a mantra, is that the show will go on until there’s no more demand to see it. Beyond that, who knows? “We’ve had an offer to go to London and an offer to go on a national tour,” says Taylor. “But no official deals.”

And if the show does hit the road, should this cast go with it? The actors–a young bunch, mostly from Chicago–have other ambitions, bills to pay, and day jobs. Boyce, a 30-year-old army vet (he served in the gulf war) works two jobs–he’s a salesman in the crystal and silver department at Marshall Field’s and a waiter at a restaurant in Hyde Park. “Hey, I can go a day with only one meal,” he jokes. “But Rolando and Tori–my kids–have to eat.”

“Black Ensemble is like a home–it’s so comfortable and Jackie’s so loving,” adds Staples. “But eventually I have to break out.”

Like the other cast members, Staples, who’s only 20 years old and just two years out of Westinghouse High School, knows there is no guarantee that a role in a popular off-Loop show will lead to fame, or even to enough money to quit the day job. It’s a matter of faith and perseverance. “You have to believe,” says Staples. “I have my dream of standing onstage in a large, large auditorium and singing a song and the audience is so quiet because I have them captured. I have so many dreams. I want to be the black Julie Andrews.”

Gregory has his own ambitions. “I feel blessed, very blessed, to be in this show, but I don’t want to be doing Jackie Wilson for the rest of my life. I’d like to do Broadway or make movies. I want to be remembered as a great entertainer who can dance, act, sing, and write my own music. I don’t want to be typecast. I want to show my versatility.”

To showcase his talents, in November he released his independently produced CD, My Name Is C.G. It’s all original music, a smorgasbord of sounds–hip-hop, R & B, inspirational.

The release party, held at Black Ensemble’s theater, was attended by about 80 people, many of them fans from The Jackie Wilson Story. The party’s emcee, V-103 deejay Gigi Hightower, made a point of the fact that Gregory would not do songs from the show. “I know you’ve seen him as Jackie Wilson,” Hightower told the crowd. “But the reason we’re here is to debut his new album, and see what he’s all about. What you are going to see tonight is Chester Gregory.”

Gregory sang five songs, including “I Want U,” a ballad dedicated to his wife that turned into a steamy dance routine with LaMisha Readus, a former dance student of his from East Chicago Central.

“I want to tell you that the woman in that dance is not Chester’s wife,” Hightower said when it was over. “Repeat that please,” Kimberly Gregory called out from somewhere in back.

Doing his R & B ballad “Last Day,” he stepped with Jackie Taylor, and then performed “Dyslexic,” a hip-hop number.

Afterward, Rosario gave him a yellow rose. “I know this was the night to feature his CD, and I thought it was great,” she said. “But to tell you the truth, I was hoping he’d do a song, just one song, from Jackie Wilson.”

Just before the final curtain Gregory does another costume change, slipping a royal blue jacket over a baby blue shirt. He finishes his Gatorade and takes one last lozenge.

The band kicks into “Higher and Higher,” Jackie Wilson’s most recognizable song.

Some of the actors jokingly call this the “resurrection scene.” A narrator has just told the audience about Jackie Wilson’s death, and the ensemble has gathered to sing a tribute to his musical legacy. After the first verse Gregory bursts back onstage, as if to say, Jackie Wilson may be dead but his music lives.

The scene’s pure schmaltz–the happy, hopeful lyrics and uplifting melody a counterpoint to the mess Wilson made of his life–but it usually works. And tonight’s no different. As the music builds, Gregory walks the rim of the stage, as if on a farewell tour. The audience claps to the music. It seems as though everyone knows the words:

Now once I was downhearted

Disappointment was my closest friend

But then you came, and he soon departed

And you know he never showed his face again…

Gregory marches up an aisle to the back of the theater, waves to the crowd, and then dashes down the back stairs to the dressing room.

The band’s still playing “Higher and Higher” as the cast comes out for its bows. Gregory’s last, of course. The crowd rises. Two women in front wave the handkerchiefs he gave them.

Gregory basks in the cheers, then takes the microphone to introduce Jackie Taylor.

She thanks the crowd for coming to the show. “Because of you we’re gonna run it forever.”

The house lights come on, the band packs up, and people put on their jackets, gloves, and hats and make their way to the lobby, where the cast is waiting. It’s after 5:30. It’s dark outside. A second show in the Black Ensemble repertoire, The Nat King Cole Story, starts in about two hours. Some of the actors are doing both shows.

Not Gregory. He’s done for the day. Well, almost. He still has people to greet. He stands by the ticket booth, hemmed in by admirers, a big smile on his face, showing no signs of his cold or fatigue.

The line creeps along. An older fellow, his back bent, shakes Gregory’s hand. “I saw Jackie Wilson years ago,” he says.

“Oh, really,” says Gregory.

“Saw him at the Regal in, I wanna say, 1962.”

Gregory smiles and the old man moves on, replaced in line by a tall woman in a long fur coat. “Baby, you were marvelous,” she tells Gregory.

“Thank you, ma’am,” he says.

“I really loved ‘Doggin’ Around.'”

The people behind her stir impatiently, but she has more to say.

“You’re gonna be big, Chester Gregory,” she says. “You’re gonna go to Broadway or wherever you wanna go. I’ll see you in the movies, and I’ll tell my friends, ‘I knew him way back when–before he was a star.'”

Art accompanying story in printed newspaper (not available in this archive): photos/Jon Randolph.