This article originally appeared in the October 2005 issue of Esquire. It is the basis for the new movie Sing Sing, starring Colman Domingo. To read every Esquire story ever published, upgrade to All Access.
Smack in the middle of Sing Sing, the old Gothic prison on the Hudson River—maximum security, with massive gray walls and octagonal watchtowers with snipers in them—Dap stands in front of a blackboard. He has an easy grin and a haircut so tight, it’s like paint. “Do you want it like Marilyn Monroe?” he asks.
He says this to Brent Buell, a fifty-eight-year-old writer and actor with a gold earring and a long blond ponytail. Then he breaks into a rousing chorus of “Happy Birthday.”
“Start taking vocal lessons,” Buell says.
It’s the first day of auditions for the prison theater program, which has been staging plays at Sing Sing for eight years. One of only three such programs in the country, it’s drawn support from the local community and Broadway actors and sparked a study by the John Jay College for Criminal Justice, which found that inmate actors have better social skills and fewer conflicts. Most of the actors are in for murders. Most are in for life.
Next up is Kareem, a somber man in a white skullcap. Seventeen years ago, under the name Kelly Watts, he beat a friend to death with his fists after he made a nasty comment to his girlfriend. Buell asks if he’s willing to share a role. “I’d be willing to do whatever you want me to do,” he says, “including dress in drag.”
Next comes Dario Pena, a handsome man with a scar that circumnavigates his head. In a rich and plummy voice he reads a speech from an old English play: “Now indeed I am a prisoner! Yes, now I feel the galling weight of these disgraceful chains!”
Buell asks him if he’s interested in any particular part.
“I’ll play anything—even a dead body.”
So Buell has him read for Dead Man Number 1.
The convicts keep coming. Guy Youngblood looks like Kris Kristofferson and reads the roles of Cannibal Pete and Matt Dillon in the same rich pirate burr. Divine Eye has long dreadlocks and massive muscles and sings “Happy Birthday” with showbiz pizzazz, throwing his arms out. Spider is a skinny white guy who looks like a bent altar boy and bows as he exits. Elijah has a Mormon beard and a middle-aged paunch and reads in a British accent straight out of Masterpiece Theatre. Patrick has a goatee and a gold tooth and lots of energy and reads for Gravedigger as if he can’t wait to bury the whole world. He sings “Happy Birthday” twice.
Then there’s Pow Wow. Tall and reserved, he listens with a wary look as Buell says he wrote a part for him, the only role he wrote with a specific person in mind. The scene is about a gladiator who wants to give up fighting and become gentle and kind, but the world won’t let him. As he reads it, Pow Wow’s eyes go big. “That’s exactly how it happened! Did someone tell you? I got into an incident.”
“Tell me,” Buell demands.
Pow Wow says he was in the yard when someone pushed him into a corner. He had to fight back. He had no choice.
Buell looks pained. “You gotta be like the Virgin Mary for the rest of the show.”
“I’m trying.”
“No matter what they do, just eat it.”
“I do.”
Pow Wow shows off a dance move.
“You want me to sing?”
Watching killers sing and dance is an odd thing. First it hits you—gosh, they’re nervous and excited, giggly and shy, desperate for appreciation and recognition just like everyone else. Then you think of what they did to get here and you feel ashamed, as if your recognition of their humanity was actually a moment of weakness. Shouldn’t these guys be punished?
“We’re not in the punishment business,” says the Sing Sing superintendent, Brian Fischer. “Going to prison is the punishment. Our mandate is a safe, clean facility.”
From a pragmatic point of view, he says, inmates who are involved in activities tend to stay out of trouble. They learn to work hard, to commit to something, to defer gratification. Underpaid guards who resent the fully equipped convict weight rooms quickly learn that the inmates with the biggest muscles tend to be the ones who cause the fewest problems. And with convicts going home at an alarming rate—630,000 a year—every bit of self-discipline they pick up is a plus for you and me, their future neighbors.
Fischer doesn’t mention the ancient idea that literature and art are an essential part of a person’s moral education, deepening our empathy for other people, but that’s implicit in the program. Rehabilitation Through the Arts, it calls itself.
But is it true? Can art really rehabilitate a man? Does singing and dancing really heal? Can slapstick save your soul?
By the second week, Pow Wow is out of the show; because of his “incident” and the death threats that followed, he got moved to involuntary protective custody. Eric comes in to audition for his part. A big, handsome guy with a shy way of reading, he laughs when he gets to cuss words. “Can you look real menacing?” Buell asks.
Eric nods, looking utterly harmless.
Afterward, Buell reads out the casting assignments. Youngblood gets Cannibal Pete and Matt Dillon, Rasheed gets Gravedigger, Spider gets Chester and Scurvy Legs, Patrick gets Merry Man Number 1 and . . .
Patrick looks alarmed. “Maid Marian?”
“Not Maid Marian—Merry Man.”
In another room, the inmates on the theater steering committee talk about how to fill the holes in the cast. They interviewed three new people on Saturday. Maybe Eric could take on another role.
“He has some trouble reading,” Buell points out.
“We’ll help him,” says Divine Eye.
“That’s what we do,” Dap says with pride.
At the third session, they have their first read through. It’s a dismal, cold day in February and you can barely see the sky through the heavy wire and ancient dirt on the windows. This is the “schoolhouse,” a brick building in the middle of the prison grounds. There are blackboards and inspirational posters. The prisoners gather the desks in a circle, each man holding a script in his lap. Most have marked their dialogue with yellow highlighter.
Written by Buell, the play, Breakin’ the Mummy’s Code, is about six convicts who each write separate plays and then splice them together into one ridiculous romp. Buell’s main creative goal was lots of parts and lots of costumes, so the play has pirates and gladiators and cowboys and a spy in a tuxedo and even Prince Hamlet of Denmark. It also has lots of play-within-a-play dialogue about prisoners on the stage. “We do these plays for RTA,” writes Buell. “And, man, for that little while, there’s no walls. We’re free. We’re soaring.”
They act hard. Kareem’s reading glasses slide down his nose. Everyone laughs when Rasheed does his cockney accent. When Spider stumbles over the word misogynist, four men shout out the correct pronunciation. When Divine Eye starts a full-bore performance of Hamlet’s “To be or not to be,” it seems almost like a Saturday Night Live routine at first, this high-flown language in the mouth of a muscle-bound convict. But he’s so serious and passionate that the moment is transformed. That’s why the groundlings came to see Shakespeare, you realize, not for the sword fights and bear baiting; the heightened language heightened them.
The loudspeaker crackles time.
As the weeks go on, the personalities of the prisoners start to emerge. Youngblood is eager to be known, confessing to a secret marriage and bringing in a sheaf of his poetry. Dap’s Mr. Cool, always smiling and collected, locking his line readings early and doing them exactly the same every single time. Winter smolders with granite silence, then flashes a winning smile. Spider is the king of jokes and sheepish grins. Bilal is the diplomat, the organizer, the stage manager. “We have to nip breaks in the bud,” he says. “Bathroom is an exception, prayers are an exception, but watch the coffee and tea runs. Otherwise it’s not fair to the team. It’s imperative we take this seriously.”
Gradually their stories come out, too. Dap’s real name is David James. He grew up in Queens with an abusive stepfather and a mother so deeply stressed that the tension came out in big red shingles on her skin. He did well in school but chose the life of a rock star, which he got through selling drugs. His luck ran out at twenty-one, eight years ago. Guy Youngblood grew up in Connecticut with his mom, a secretary, tangled with his stepfather, and got into drugs and ended up a teenage runaway living on the street. When he was twenty-five, eighteen years ago, he killed a man in a drug deal. Winter is Lamont Bryant of the Bronx, arrested “due to circumstance rather than criminal talent—a love triangle.” He was twenty-five then, six years ago. Spider grew up in a small town near the Canadian border under the name Brian LaBrosse, adopted son of a nurse and a heavy-equipment operator. A high school dropout with a record of minor crimes, he got arrested five years ago for a killing he describes as a hunting accident. Bilal was Dexter Robinson of Brooklyn, stepson of a military officer. He’s been inside for twelve years for a double homicide with gang involvement. “If people needed to sleep,” he says, “I made them sleep.”
With the most shocking story, Kareem turns out to be the most impressive man. Dignified and studious, an elder statesman of the tiers, he’s earned a BA and an MA, works as an aide in the family workshop and youth-awareness programs, and teaches a religion class to other inmates. Superintendent Fischer singles him out as a model prisoner worthy of a letter to the parole board, the kind who knows the difference between “making a mistake” and committing a crime.
“I know what resides inside me,” Kareem says.
Once, Buell let a homeless man stay at his house for a weekend and the guy ended up staying for two years. After four years of volunteering, it’s still emotional for him to go in and out of the prison, walking through all those steel doors and then back out again, free to go to a movie or a store on a whim. He gushes about the prisoners and their breakthroughs and talents.
Time for an acting exercise. Everyone stand in a circle and raise your arms. Get as tall as you can and then get a little taller and then bring your arms down and feel tall. That’s called taking the stage. “You see actors in real life and they can seem very small,” he says, “but onstage they seem very big.”
He starts to block scene five. “Have you thought about how funny ancient Egyptians might move?”
With him in charge, giving them permission, silliness slips through the room like a contagious giggle. In the black-plague scene, the convicts mug spectacular deaths, hooting as the bodies pile up on the floor. Buell suggests they come back to life for a second and die again, so they shoot out their legs and gasp for breath and bulge their eyes. “Try to move like you’re rotting,” he says.
Lying on the floor, they squirm and twitch.
Today is a sunny spring day, golden light coming in the Venetian blinds. First some stretching exercises and jumping jacks and then the big ending dance number to get everyone pumped. Now meet Kim Breden. She was in The Phantom of the Opera in Germany, and she’s here to help you sing. “It’s all about using the best tools to tell your story,” she says. Start with proper breath support and diction. Take a deep belly breath and then hiss it out. “If you have long lines to say, this is a great exercise.”
Next she asks them to hum: “Fill your head with sound! Project it to the back of the theater!”
Now smile on the inside. “Listen to what happens to the tone.”
“It went up!”
“Yes. Thank you. If you want to bring up the pitch, you can smile inside.”
It sounds like a hive of bees, everyone humming, looking for that inner smile.
“Where do you feel it?” she asks.
Elijah points to his nose.
Then they follow her up the scale. “Guys, the vocal cords are a muscle. You must work with them like any other muscle . . . ma me mi mo mu . . .”
She takes them up in half steps and nags them about diction: “Every single consonant matters. You are telling a story. You can’t leave anything out.”
Pretty soon they’re booming like marines: “Hut hut hut. Mutt mutt mutt. Sutt sutt sutt.”
“Keep that smile inside,” she says. “You have to charm the audience.”
Waiting for his scene, Winter offers up a rap:
All the time, every time I turn around
I’m falling victim to these temptations.
As a kid, he was curious about the stars and dreamed of becoming an astronomer, he says. But his life seemed to be going in slow motion, and he went from making up rhymes about money and violence to living them. Arrested at seventeen for armed robbery, he spent a year in the Elmira prison. “I thought it was a rite of passage. That’s what rappers taught me. That’s the bullshit I swallowed.”
I’m calling, I’m calling
I’m falling, I’m falling
Walls are closing in,
The doors ain’t opening
A couple of years ago, one of the RTA guys heard him rapping in the yard and suggested he give acting a try. He worked with a volunteer named Joanna Chan for five months to develop the character of a fifty-year-old man in August Wilson’s Jitney. In her sixties, Chan looks and sounds like a sweet Chinese grandma. But she’s a political dissident and a Maryknoll nun and a published playwright and a person of infinite persistence, and the prisoners have surprisingly intense feelings for her. “I love Joanna Chan,” Winter says. “I would do anything for that woman.” The more he studied his character, the more he understood him. “It was like putting on my grandfather’s clothes,” he says.
Many of the prisoners tell similar stories. Kareem was in rehearsals for weeks, playing a man whose life went sour when his son went to jail, when he finally realized he was playing his own father. Seeing it through the character made it easier to face. One day in the visiting room, he said, “I’m sorry for what I put you through. I put you through a lot.”
He had never said that to his father before.
Late in April, they start rehearsing in the prison auditorium, a big, echoing space made out of brick and steel. Even though there are no guards in sight, everyone stays serious and focused. “Next scene!” Buell calls. “Where’s Zakariedies? Where’s Double-O?”
In the audience, Superintendent Fischer sits with two charity-minded women from the local community. The old curtain is torn and frayed, patched by convicts with fishing line, and they’re here to decide whether to donate $4,600 for a new one.
Double-O comes out in character, shadowboxing. “We specialize in grotesque violence—line?”
“Skewering! Flailing!”
He picks up the line and keeps going, working into a crazy, smiling-killer thing that is genuinely scary. “Muzzle the gladiator!” Buell cries, happily.
Grinning, Double-O makes it bigger. By the closing dance, he stomps out like a monster and keeps on dancing in the background till the music stops, giddy with the moment. The women agree to pay for the curtain.
Katherine Vockins is the founder and producer of RTA. A thin and elegant businesswoman from a nearby suburb, she was working in marketing and remembering her teenage theater days when she heard about a group of prisoners who had an interest in playwriting. She went in for a look and came out hooked. Tonight she drags in three big suitcases stuffed with costumes and waits at the gate as a guard checks items off a list: one purple cloak, one wedding veil, one pink full-length gown, one pirate hat, eight cowboy hats, eight eye patches . . .
In the auditorium, saws buzz and the actors lounge in the house seats, waiting. A crew of prisoners has been working for two weeks on the sets. Two carved planks move back and forth for waves, a bathtub doubles as a boat and a bier, a mast with a Jolly Roger suggests a pirate ship, and there’s a bike made entirely of wood that says MY SON IS AN HONOR STUDENT AT SING SING VOCATIONAL. Vockins gathers everyone and asks them to be vigilant about costumes and props. In fourteen shows, she says, they’ve never lost anything. “Be responsible.”
“Let the dragon out!” Bilal barks.
It’s a chaotic scene. Youngblood arrives late and has to do his speech in prison green. Thai Chi forgets to change a set. Random prisoners drift through the auditorium on their way to somewhere else. There’s a new actor filling in for Double-O, who dropped out of the show due to creative differences. Buell yells, “Double time! Exit fast! I’m tired of people walking slow!” Afterward, he tells them to speak louder and more clearly, be aware of where the floor mics are.
But backstage, Youngblood has a dark expression. “My wife was supposed to come, and she didn’t show up,” he whispers. “I don’t know why. And I blew my lines. And I can’t dance to this music.”
In his funk, he starts to vent. He wanted to try out for the lead, but let’s face it, the program is geared toward African-Americans. They say it’s a family, but it’s not. “Me and Spider are the only white guys, and we get the most foolish parts.”
Buell overhears him. “Leave it behind!” he says. “You can be happy here! Be happy!”
“I’m in a mood,” Youngblood says.
Then it’s opening night and the prisoners of B block file into the auditorium. They’re the roughest guys at Sing Sing, the hardest audience, big guys with huge muscles and scarred faces. Backstage, the cast forms a circle, holding hands. “Now is the time when all the hard work pays off,” Buell says.
After a moment of silence, they shout in unison: “RTA!”
The show starts slow, with a trickle of laughs for physical humor—a bouncing cannonball, Kareem’s shtick with a scarf and a beret, Winter pretending to stab himself. Joke by dumb joke, the audience warms up. They applaud when Maid Marian slugs Robin Thug. A play on Snoop Dogg’s “fa shizzle my nizzle” routine goes over big. They love the sawtooth waves and Hamlet’s unexpected dignity. In this harsh world of stone and steel, the silliness feels like an achievement, a judo flip that turns pain into hope. Youngblood’s wife came to visit this morning and they got into a fight so bad he had to walk out to keep from getting crazy, but he gets a laugh when he lists all the antidepressants he’s taking to survive cowboy life. Even the mistakes seem like a metaphor for how to live. When a crew member rushes a forgotten prop out in mid-scene, Dap just grins and makes it part of the scene: “That wasn’t there a minute ago!”
When he dances the waltz, his partner looks so delicate and lovely in her lacy white dress, the house goes quiet. Row after row, the fearsome men of B block light up with gentle smiles.
When it’s over, B block gives them a standing ovation. “Thank you!” Kareem shouts out. “We do it for y’all because we love you!” Backstage, the feelings are surprisingly intense, an explosion of sudden joy and brotherhood that’s very moving to see. Spider lifts Dap up off the floor and Kareem hugs Bilal hard and Bilal tells everyone, “I’m proud of you, I’m proud of you.” Rasheed is thrilled with his first performance. “The crowd was supportive,” he says, amazed. Divine Eye is beaming. “Did you see how quiet it got when I did the Hamlet joint? ‘Oh shit, he’s really doing it!’”
In this moment, there seems to be no doubt: Art heals, slapstick saves, killers can become comedians. Even Youngblood is happy. Soon he will go back to brooding on his troubled marriage and wasted life. But right now he wants to bask in the moment. “I got to be someone else for a while,” he says.
He grins and tips his cowboy hat.
Read more great John H. Richardson stories:
- "My Father, the Spy"
- "When the End of Human Civilization Is Your Day Job"
- "The Joy of Sex with One Woman (My Wife)"
