As indicated by its title, Sing Sing is set in the maximum security prison in Ossining, New York, 30 miles north of Midtown Manhattan. Unlike many films set in American prisons, the film focuses on an actual rehabilitative program. Rehabilitation Through the Arts (RTA for short) operates in six New York State prisons, bringing workshops on a variety of artistic mediums to over 230 incarcerated men and women. Inspired in multiple ways by true stories from the program, Sing Sing is beyond powerful. It’s a deep, delicate dance with humanity, grace, and wisdom.
The incomparable Colman Domingo stars as John Whitfield, an inmate stuck in Sing Sing for several years for a crime he did not commit. We come to understand his innocence fairly early on, as part of the film’s plot revolves around his attempts at being granted clemency. Enter the first of many actors in the film who are alumni of RTA programs: Clarence Maclin as himself. Clarence is innocent as well but has resigned himself to being incarcerated for a good chunk of his adult life. He presents himself as nothing more and nothing less than the toughest new guy in the yard, but as he and John bond in their RTA theatre program, Clarence blossoms, both as an actor and a human being.
A certain unspoken jealousy arises between the two men, but this plot point never feels forced. Director and co-screenwriter Greg Kwedar and his incredible cast have a way of getting that tension across in subtle, unconventional ways, consistently grounding their conflict in truth. John holds the RTA program near and dear to his heart. He was heavily involved in the arts before a seedier chapter of his life began, and he spends much of his time in his cell writing plays which the troupe performs. When Clarence suggests that their next play be a time-traveling comedy and the program’s leader Brent (Sound of Metal’s Paul Raci) volunteers to write the script, John feels slightly put out. This annoyance grows when Clarence is eventually cast in the role of Hamlet (not the main character of this particular show, but enough of a part to get to deliver the ubiquitous “to be or not to be” monologue). John’s humanity wins out, however, and he soon makes a friend of Clarence, seeing himself in Clarence’s anger at the world. Soon, John is helping Clarence on his reluctant path to clemency.
If it sounds like I’ve given away the whole plot of Sing Sing, don’t worry, because I haven’t. So much of this film revolves around how it employs the talents of the other RTA alumni in its cast. They influence the tone of the film and main thrust of its story every bit as much as Domingo and Maclin do. Everyone in the film’s troupe gets a chance to share at least a glimpse of their story, and these searingly emotional moments often sneak up on us, blindsiding us with raw vulnerability. What’s more, these moments aren’t just for show: the film is paced such that it has a sense of building, beautiful catharsis. One particularly stunning moment showcases former inmate Sean Dino Johnson, playing himself, earnestly coaching Clarence and coaxing him out of a certain insular worldview. His words snap us to attention, elevate us, and break our hearts in one fell swoop.
As brilliant as the totality of the film is, it’s worth emphasizing just how sensational its two lead actors are. John and Clarence are two sides of an internal dilemma in prison: should I retain some sort of hope for the future, or should I just give up? The representation of this conflict and the story of finding friendship in the midst of tragedy are made unforgettable in their dazzling nuance. Anchored by Domingo and Maclin, Sing Sing achieves a one-of-a-kind uplifting honesty. | George Napper
