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How the prison-set ‘Sing Sing’ captures the magic of acting

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The new movie “Sing Sing” is set in the maximum-security correctional facility of the same name, a gray and Gothic structure in upstate New York that’s designed to punish its sentenced inhabitants. But the majority of the film takes place in an expansive auditorium, with vaulted ceilings and large windows that bathe the space in natural light.

It is here that a prison theater group meets multiple times a week, sometimes for a few hours, sometimes all day. When working, they are not incarcerated men, but swashbuckling pirates, Old West cowboys and Shakespearean antiheroes. They play improv games, try on costumes, recite lines and rehearse with props; they laugh, cry and embrace their many emotions, as all the best storytellers do.

As one incarcerated actor puts it in the movie, “Brother, we’re here to become human again.”

The line doubles as a thesis statement for “Sing Sing” itself. Inspired by the true stories of those who took part in a unique real-world theater program, the intimate, captivating drama is arguably one of Hollywood’s most precise portrayals of acting — not merely as a vehicle for expression or the basis of a global industry, but simply as an exercise of imagining yourself to be someone else for a moment. When practiced communally, the pastime of playing pretend can yield powerful, lasting changes.

“Sing Sing” arrives in theaters today after collecting an audience award at South by Southwest, numerous favorable reviews and much Oscar buzz. Director Greg Kwedar credits the film’s reception to the foundation set by Rehabilitation Through the Arts, the volunteer-run theater program founded at Sing Sing in 1996 that has since expanded to dance, music, visual arts and creative writing across eight New York state correctional facilities.

“Because of how the program approaches acting as a tool for self-development, there is an intense openness that’s happening in front of the camera,” the filmmaker says in a Zoom interview from San Francisco earlier this week, “a vulnerability to just be uncomfortable and go for it that’s been built among the men through years of trust.” Kwedar, 39, and his co-writer, Clint Bentley, 38, developed their screenplay while shadowing rehearsals, participating in workshops, attending performances and meeting with RTA alumni, who make up 85 percent of the film’s cast and play versions of themselves.

Colman Domingo, center, and the cast of “Sing Sing.”

(A24)

While professional acting companies generally stage classic texts with an emphasis on factual accuracy and dramaturgical logic, RTA instead prioritizes each actor’s emotional authenticity. Theater buffs will notice this freedom right from the start, when “Sing Sing” opens with “Rustin” star Colman Domingo, 54, portraying the program’s founding member John “Divine G” Whitfield. He’s performing onstage in the prison’s production of “A Midsummer Night’s Dream,” reciting Lysander’s lines (“The course of true love never did run smooth”) with a full commitment — and while donning a gold crown.

“Why is he wearing that?” Domingo asks on a video call, laughing. “He’s not a king, he’s one of the lovers. Maybe it’s because that’s just the costumes they had. But regardless of why, that’s a choice that makes sense to these actors: Our Lysander wears a crown — where’s the problem?”

RTA’s unwavering dedication to looseness is rare in the theatrical world, rarer still in the prison world. “We all tell ourselves that there are rules in place about who we are and how we have to be,” Domingo adds, “but what RTA says instead is, you don’t have to be any of the things that have been impressed upon you, the history you came in here with or the trauma you’ve suffered. You can actually liberate yourself and become something new. I think we as viewers long for that, to give ourselves that permission so freely.”

“Sing Sing” follows a group of incarcerated actors through their new production: an original time-traveling comedy that includes (but is not limited to) Egyptian mummies, gladiator battles, dance numbers, a “Hamlet” monologue and a Freddy Krueger cameo. The play’s premise is pulled directly from a 2005 Esquire article about the prison program that initially caught Kwedar’s attention, but the movie is focused less on “Breakin’ the Mummy’s Code” than the incremental progress of learning to see yourself as a person capable of creativity and rebirth.

Clarence “Divine Eye” Maclin plays a version of himself in “Sing Sing.”

(A24)

“It was cathartic, because I got to work out a lot of frustrations and tensions, examine them through playing other characters, and see life through other eyes,” recalls Clarence “Divine Eye” Maclin, 58, who, while incarcerated, initially wanted to join RTA to flirt with female volunteers. He went on to lead Sing Sing productions of “West Side Story,” “Jitney” and “Oedipus Rex.”

“I was always enthusiastic about going into rehearsal because I was entering a space of freedom, a space where I know I’m going to get some healing and have a good time,” he adds. “I know people probably never would think that, because it’s prison. But that space was not prison, that was our space. And doing plays and creating and having volunteers come in from outside who actually view me as a human being where my opinion counts — that was a beautiful way to exist in a place that wanted to try to deny my existence.”

Over the course of “Sing Sing,” between the play’s auditions and opening night, the actors rigorously prepare for their roles with dance battles, sword fights and improv games — the latter of which were not fully scripted but attempted fresh on set, led by “Sound of Metal” Oscar nominee Paul Raci, who portrays longtime RTA volunteer-playwright Brent Buell.

These sequences of unabashed, autonomous play “were hard to calibrate,” says Kwedar, “because you don’t want to trivialize what’s happening, which is actually quite significant. These were moments of childlike joy in the acting process that were like full-throated screams of exultance. We made sure that the camera was rarely ever looking away and always moving closer, and dancing with the same freedom that the men felt in that space.”

Domingo calls the inclusion of such images of vulnerability between men — especially men of color — a radical act. “The world doesn’t see us that way,” he says. “We’re usually depicted with hypermasculine, hardened, deteriorating examinations of who we are, which then makes people think of us in a certain way in the world. But what I and my co-stars know to be true is that love, sweetness, playfulness and brotherhood are always available.”

James Williams, left, and Sean San José in the movie “Sing Sing.”

(A24)

Kwedar says that he and Domingo agreed that “Sing Sing” should be, “above all things, honest, elegant and tender” — words that one usually wouldn’t use to describe a movie set in a prison. Rather than replicating the genre’s violent and dehumanizing clichés, the director instead presents yard scenes outside the theater group’s work with a stillness, “like a Greek chorus that doesn’t have the freedom to move, the permission to speak or the ability to convey any kind of love or emotion. To me, that kind of numbness felt more horrifying than any bloodshed.”

“Sing Sing” was filmed over 19 days in July 2022, across multiple decommissioned correctional facilities, a tough environment to be in, both logistically as well as for formerly incarcerated actors to return to, even with a counselor in tow. “It’s all concrete and there’s just no airflow,” says co-writer and producer Bentley. “But whenever the alumni were filming together, they brought so much joy that it far surpassed any of the misery of filming in that place. Walking into the space they’d created was like walking into color in ‘The Wizard of Oz.’”

The film closes with footage of jubilant curtain calls from actual Sing Sing productions, material captured by RTA over the years not just for posterity, but to send home to family members of incarcerated cast members. The movie doesn’t concern itself with who gave the best performance in the show, nor does it say who goes on to become a professional actor once released. It’s not interested in those things.

“The acting we’re trying to interrogate in this film is not about performing for an audience on opening night,” says Kwedar. “There’s a kind of falseness that can happen when you’re just memorizing lines and being technically excellent. It’s when you can step outside of yourself and look through someone else’s eyes that your capacity for empathy is unlocked and a deep truth comes through. And what that starts to build in you is something that is unparalleled.”

Director Greg Kwedar, left, and Colman Domingo on the set of “Sing Sing.”

(Phyllis Kwedar / A24)

“Sing Sing” makes clear that acting is hard work, creativity is a muscle worth exercising and dreaming is a discipline best taken seriously. Domingo and Maclin’s initially discordant characters discover a healthier perspective of each other and themselves; all those silly improv games and blocking rehearsals create an empathy and openness that allows them to forge a friendship. A real kind of rehabilitation has happened.

This resolution mirrors the facts: A 2011 John Jay College for Criminal Justice study found that those who participate in RTA programs have better social skills and fewer conflicts while in prison. And according to RTA, less than 3% of RTA members return to prison as repeat offenders, compared to 60% of incarcerated people nationally.

Such results make for a strong argument for anyone, incarcerated or otherwise, to give the transformational power of acting a try.

“I hope we are aware of our power, of what we have to offer,” says Kwedar. “If this can happen inside Sing Sing, it can happen anywhere. We don’t have to settle for misery. Art is as vital as the air we breathe and wherever people have access to it, they can thrive.”

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