Sing Sing, directed by Greg Kwedar, is a deeply moving exploration of the transformative power of art within the rigid confines of the American prison system. The film is set in the infamous New York correctional facility and centers around a group of incarcerated men who participate in Rehabilitation Through the Arts (RTA), a program designed to teach life skills and foster positive change through the medium of theater.
What sets Sing Sing apart is its authentic approach to storytelling. While the film could have been a straightforward documentary, Kwedar opts for a scripted drama that blurs the lines between fiction and reality. The cast is made up largely of non-professional actors, many of whom are formerly incarcerated alumni of the RTA program, lending the film an undeniable sense of realism and intimacy. Colman Domingo, fresh off his Oscar nomination for Rustin, leads the cast as Divine G, a man imprisoned for a crime he didn’t commit who finds solace and purpose in the world of theater. Domingo's portrayal is a masterclass in subtlety and depth, his performance anchoring the film with both power and grace.
The story, co-written by Kwedar and Clint Bentley, is based on a true story first explored in John H. Richardson’s 2005 Esquire article “The Sing Sing Follies.” Yet, the filmmakers took their research further, re-reporting the events and interviewing real participants of the RTA program. This approach pays off in moments where the inmates share their stories and experiences. When Sing Sing has to move the plot, the usual clichés of prison dramas begin to creep in. The drama usually unfolds in a way that feels organic, especially in the scenes that depict the theater group’s rehearsals and discussions. However, the third act struggles to feel as natural. One plot moment, involving the death of a character, in particular feels forced.
At the heart of the film is the relationship between Divine G and Clarence “Divine Eye” Maclin, a newcomer to the RTA program played by Maclin himself. The dynamic between the two characters initially hints at a potential rivalry, but Kwedar wisely sidesteps this trope. Instead, the film delves into the complexities of their evolving friendship, rooted in mutual respect and shared passion for the arts. Maclin’s performance is particularly striking, his raw, unpolished energy contrasting with Domingo’s more seasoned presence. The interplay between these two characters forms the emotional core of the film and is the reason to see the film.
Sing Sing's portrayal of the harsh realities of prison life is well done, often contrasting moments of humanity against the loss of human decency within daily life. Kwedar doesn’t shy away from depicting the dehumanizing aspects of incarceration—the arbitrary punishments, the constant surveillance, the cramped and cluttered living conditions. Yet, within this bleak environment, the theater program emerges as a beacon of hope, a rare space where the inmates can express themselves freely and rediscover their humanity. One of the most poignant moments in the film comes when Divine G, after a particularly grueling rehearsal, steps outside and tilts his face up to feel the breeze—an image that speaks volumes about the small, hard-won joys that the program brings to these men’s lives.
While the script occasionally leans too heavily on predictable emotional beats, and there are moments where the film’s dramatic elements feel somewhat contrived, Sing Sing is still a winning film. The focus on the relationship between Divine G and Divine Eye, while compelling, sometimes overshadows the ensemble nature of the story, reducing other characters to mere background figures.
Sing Sing is a powerful testament to the enduring value of art and its ability to foster empathy, even in the most unlikely of places. It’s a film that not only sheds light on the transformative work of the RTA program but also challenges audiences to reconsider the role of the arts in our society.
4/5
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