Rehabilitation Through the Arts (RTA) is a unique program at the infamous maximum security Sing Sing prison where inmates find peace, purpose and presence in their lives through the magic of theater.

Filmmakers Greg Kwedar and Clint Bentley make films about human connection in impossible places as seen in their movies Transpecos and Jockey. A touching film of about a group of men putting on Shakespeare plays at the Sing Sing Correctional Facility is right in their wheelhouse.

Their main concern was avoiding as many of the clichés, stereotypes, and tropes seen in prison dramas as best they could. Sing Sing is a film about a group of incarcerated men, some seemingly innocent, some convicted of violent crimes and all disconnected from their families and friends on the outside.

Rather than emphasizing a social narrative, finding god, or determined to go on the straight and narrow, the cast of Sing Sing tapped into their higher selves through theater. They visited a previously unknown spiritual plane through the arts where they were more part of a community of men rather than inmates that needed to be punished. These men found a forum to understand themselves and their potential.

Greg Kwedar & Clint Bentley

The beauty of the RTA program was highlighted in a 2005 Esquire article by John H. Richardson titled The Sing Sing Follies by John H. Richardson, about a time-traveling musical comedy called Breakin’ the Mummy’s Code. It was as silly and irreverent a production as it sounds. The key side effect of the program was its remarkable effectiveness in reducing recidivism because it acted as a north star for these men.

A Tale Of Two Tones

Kwedar was attracted by the sharp tonal juxtaposition of the drudgery and monotony of prison life and the wacky playfulness of a wacky comedy. This tonal see-saw set the framework for Sing Sing. But Sing Sing wasn’t going to default to the traditional prison drama genre. It wasn’t going to simply be about a prison program. It is a film about remembering those members of our communities who are conveniently forgotten and honoring them by showcasing their artistic talents and shining a light on their masculinity.

Kwedar and Bentley needed a unique angle into the story. They couldn’t proceed without including RTA alumni in their film who were both consultants and actors.

The filmmakers volunteered for the RTA program using films such as Selma, Saving Private Ryan, Dead Poets Society, and 12 Angry Men in their workshops. One of their most striking observations was the desire and curiosity of these men to step out of the regimented prison routine and embrace the silliness that accompanies making art. They were less on edge by constantly thinking in survival mode. It was time to play.

The prison world of the film was clearly defined, but the characters were not in the traditional screenwriting sense. There were so many of them each with a uniquely fascinating story to tell.

Divine G {Colman Domingo} Photo courtesy A24

The filmmakers ended up with a script that captured the essence of these men’s stories. Some characters were based on real people and others were hybrids.

“We’re always in search of the arrow shot through that world,” state the filmmakers. Dissecting and understanding these characters and examining how the program changed their lives was their goal.

Eventually Clarence “Divine Eye” Maclin and John “Divine G” Whitfield (Colman Domingo) became the bedrock characters for Sing Sing. There was less emphasis placed on who these men were and where they came from. Instead, Kwedar and Bentley focused on who they would become – two intense men molded by the school of hard knocks and tough lessons. Furthermore, the real life versions of these men were instrumental in helping the filmmakers craft the prison dialogue. “They went underneath the hood,” note Kwedar and Bentley.

Crafting characters convicted of serious crimes while goofing around during rehearsals was a challenge they heartily embraced. There was an instinct and raw energy to these characters as they redirected their energies from destroying to creating something of beauty.

Each character brought the vulnerability of their lives to the screen without excessive syrup or mawkish sentiment. There was no judgment or pity; only a commitment to staging a fine play. They made their costumes with child-like enthusiasm with whatever they could get their hands on.

The screenplay for Sing Sing went through many iterations. Notably, there were many tightly-scripted scenes as well as space for the men to experience emotional moments, especially during their improvisation circles. An example was when they closed their eyes and imagine a perfect place. “We’re here to be human again,” one actor says.

Sing Sing is a tale of becoming, a tale of healing and joy with plenty of room to breathe, meditate and wonder.