Review: Sing Sing

“Dying is easy. Comedy is hard.” Actor Edmund Gwenn’s dying words are ruefully referenced in Sing Sing, a drama set in the maximum security prison of the same name in upstate New York. This idea has rarely been more true than here, where lives can be lost due to violence or simply bad luck, and finding humor can seem impossible. Yet Sing Sing is full of hope and moments of joy, treating its incarcerated characters with the humanity they deserve, dwelling on who they are now rather than what actions may be in their past.

Divine G (Colman Domingo, also an executive producer) is incarcerated at Sing Sing, where he is serving a sentence for a crime he didn’t commit. Despite this injustice, he finds pride and community in Rehabilitation Through the Arts (RTA), a theater group composed of men at the prison and directed by volunteer Brent (Paul Raci). After a rousing performance of A Midsummer Night’s Dream, the group is ready for something different. Divine G offers the latest play script he has written, but a newcomer to the group, Clarence “Divine Eye” Maclin (playing himself), pushes for something a little lighter, given the darkness that permeates their daily lives. They practice the original comedy written by Brent to get it ready for an audience, but tragedy threatens to upend all their efforts.

Domingo is simply tremendous in this role that allows him to do both Shakespearean monologues and modern-day interactions with those around him at Sing Sing. Meanwhile, in addition to Maclin, most of the primary cast outside of Oscar nominees Domingo and Raci honed their craft in the RTA and play themselves. Sing Sing is a moving story on its surface and artfully made overall, but this behind-the-scenes fact elevates it into something truly special and worthy of praise. The results are often striking and wildly affecting, and these formerly incarcerated men turn in performances that largely feel in line with what you’d expect from a solid indie film. 

These characters are given the opportunity to do something rare in both real life and on screen. The men are encouraged to be vulnerable with each other in ways that aren’t frequently a part of the male experience, especially in how life in prison is depicted in film and TV. The acting exercises let them be alternately silly and emotionally open with one another, and it isn’t just in pursuit of their art. Their work pushes them to be better people and relate with more thoughtfulness to one another both on the stage and in life. 

Given its setting, Sing Sing plays with both space and time. In an early scene, director of photography Pat Scola shoots up through a fenced-in stairwell at the prison. A shot through stairs isn’t an uncommon one in cinema, from Vertigo to Shallow Grave, but it takes on new resonance with the cages surrounding the steps. Handheld camerawork brings us in close with these men and gives Sing Sing a naturalistic feel rather than overly stylized one, while still providing some quite beautiful images. The men’s audition scenes are all delivered directly to the camera, letting the audience experience the actors’ talent and striving directly, without any mediation. Director and co-writer Greg Kwedar gives seemingly simple dialogue scenes the chance to open up, allowing them to last longer than sometimes feels comfortable, but these moments between men are often all they have. Sometimes, Sing Sing drags a bit, but it’s simultaneously a privilege and a pleasure to spend time with these people, both as actors and as characters. 

While I was watching another movie, the Sing Sing trailer played during the previews, and by the end of its two-and-a-half minutes, my eyes were welling up, just like they did when I watched Sing Sing days earlier. Kwedar, Domingo, and these actors have partnered to create a moving testament to the power of human connection and creativity, and it sticks with you. Sing Sing speaks to how relationships and art can create hope and resilience even in a place often filled with sadness and violence, and its own existence reinforces this idea.

“Sing Sing” is in theaters Friday.

Kimber Myers is a freelance film and TV critic for 'The Los Angeles Times' and other outlets. Her day job is at a tech company in their content studio, and she has also worked at several entertainment-focused startups, building media partnerships, developing content marketing strategies, and arguing for consistent use of the serial comma in push notification copy.

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