30 miles north of New York City, situated directly on the bank of the Hudson River, lies Sing Sing, a maximum security prison that has been operational for nearly 200 years. For much of its lifespan, the institution has been known for its harsh conditions—it was the site of frequent electric chair executions until New York abolished the death penalty and is known for treating those imprisoned there with a severe sense of discipline and regulations. But by the late ‘90s, it had also become the founding location of the Rehabilitation Through the Arts (RTA) program, which brings in theater creatives to work with the incarcerated population on developing and performing their own plays, offering a sense of community and camaraderie which has proven to have positive effects on the men. The program now exists at five other New York prisons.
Greg Kwedar’s sensitive, joyous Sing Sing does more than simply dramatize the workings of the RTA program, it incorporates participants into the very fabric of the film’s DNA. Most of the cast is composed of former New York prisoners who had gotten involved in RTA during their incarceration, turning the film’s depiction of a prison theater production into a reflection of honest, shared experiences by the performers. But, while much of Sing Sing’s success is owed to the moving nature of these men’s reality, they are not used as props. Sing Sing is an emotional prison drama that doesn’t beg for your tears amid all of the typical heartstring-tugging signifiers that come with the genre’s territory. It represents these lives sincerely and avoids grandiose histrionics, melding the real experiences of these men within the fantasy of filmmaking to find graceful emotional truths.
The element of unreality comes in the form of Sing Sing’s lead performer: Colman Domingo portrays an interpretation of the real-life John “Divine G” Whitfield, a long-time participant in RTA who now helps lead the program, alongside being a hobbyist playwright when he’s not working on how he’ll convince the review board that he deserves parole for the crime that he was wrongly imprisoned for. We meet him on stage delivering a climactic moment in A Midsummer Night’s Dream, the culmination of what was surely weeks of rehearsal. But the members of RTA don’t rest, and the crew immediately convenes to decide their next project.
They’ve also just introduced a new face into the mix: Clarence “Divine Eye” Maclin (Maclin plays himself; he and the real Whitfield have story credits on the film), a hardened prisoner that we first meet threatening someone in the prison yard over money missing from a drug deal. But Divine G sees something more in him. Divine Eye is brought into the new brainstorming session, where he derails the idea of doing Divine G’s own drama The Fine Print, and instead suggests they go for comedy since life in prison is hard enough as is. This prompts everyone to start throwing ideas out and the final, original script assembled by the project’s director Brent Buell (Paul Raci) ends up a 140-plus-page concoction of wildly disparate ideas and characters amalgamated together: Hamlet, Egyptian princes, pirates, cowboys, Freddy Krueger, and time vortexes are all integral to the story. The men get to work immediately.
This was a real play written by the actual Brent Buell, called Breakin’ the Mummy’s Code, as documented in John H. Richardson’s Esquire article “The Sing Sing Follies,” which inspired this film. The heart of Sing Sing lives and breathes in the world of theater, but more broadly acts as a statement regarding the importance and universality of artistic creation. Much of the story’s first half takes on a lighthearted tone and is frequently very funny, but without disruptively ramming jokes in to try and get a laugh—these guys are just funny, and their work in RTA is portrayed as a blissful source of light and creativity within a system built to otherwise control and dehumanize them. Sing Sing recognizes the inherent humor in watching a group of stereotypically intimidating maximum-security prisoners embracing the vulnerability and potential embarrassment of auditioning, getting loose with vocal and physical warm-ups, and donning silly costumes to inhabit a made-up world. It also treats their work seriously and celebrates their commitment to doing it right. It helps that the majority of the troupe has been in RTA for a long time by the start of the movie, and already knows the power of that escape—they’ve formed a family.
Divine Eye becomes the one hold-out. This being his first production, he’s hesitant to embrace the silliness of exercises like Brent having the group walk around like zombies, or to fully embody his character of Hamlet with passionate line readings as opposed to flippantly dictating them from the script. He’s defensive and reverts to his destructive tendencies as he’s guided out of his shell by his fellow actors—particularly Divine G. The burgeoning relationship between the two is as much a crux of Sing Sing as the depiction of theater, beginning as terse peers but eventually developing into a mutual bond cultivated within the artistic process.
It’s a thread that implicitly, sharply shows us the impact of RTA, and adds backbone to story beats that threaten to veer into stock prison drama towards the back half. The latter portion of Sing Sing introduces directions that feel more familiar and primed for melodrama—tragedy within the group, the possibility of parole brought more directly to the forefront—but Kwedar and Clint Bentley’s screenplay does well to keep the emotions grounded within a naturalistic demeanor. It also works to effectively complicate the dynamic between Divine G and Eye, whose teacher-student relationship reaches a breaking point where it becomes necessarily flipped. Suddenly, Sing Sing isn’t simply a movie about one man experiencing the power of the arts, but about how such a program acts as a consistent source of sanctuary for everybody involved. You may regress, but if you open yourself up to the community it will open itself up to you once again.
This grounded naturalism also comes from the shooting style. Cinematographer Pat Scola captures events on 16mm film, and the final product is wonderfully textured and vibrant. Flashy camera theatrics are abandoned for a concentration on the performers, and every first-time film actor populating the screen effortlessly fills out the frame. No one sticks out as a non-professional actor, and if I hadn’t known any better, I’m convinced I would believe everyone was a certified SAG member. Maclin is the most impressive, given that he gets the most meat of the story and must regularly trade lines with Domingo, an actor whose raw sense of emotional transparency continues to radiate. If Maclin simply did his best to keep up with Domingo’s skill it would be impressive; the fact that he matches his passion and tenacity is incredible.
More than anything, Sing Sing’s most productive quality is how it builds out cathartic character development through the process of creating art, and in doing so carves out a space for men to express a level of emotional honesty that’s typically discouraged. In breaking down the barriers of masculinity, these men are afforded a new chance to reclaim an emotional vulnerability that the world desperately wants to erase from them—as both prisoners and, largely, as men of color. In Sing Sing, healing is forever an ongoing process, but one you’re never alone in accomplishing.
Director: Greg Kwedar
Writers: Clint Bentley, Greg Kwedar
Starring: Colman Domingo, Clarence Maclin, Sean San José, Paul Raci
Release Date: May 4, 2024 (Atlanta Film Festival)
Trace Sauveur is a writer based in Austin, TX, where he primarily contributes to The Austin Chronicle. He loves David Lynch, John Carpenter, the Fast & Furious movies, and all the same bands he listened to in high school. He is @tracesauveur on Twitter where you can allow his thoughts to contaminate your feed.