Starting a discussion on a film with a personal anecdote is not always appropriate, since the conversation should be about the artistry on display, rather than a bundle of memories. However, while watching this film, I was reminded about a visit I took during high school to a local prison as part of an educational field trip based around showing students the reality of life behind bars (and to hopefully dissuade any juvenile troublemakers from turning to a life of crime) – and after hours of talking with guards and residents of the facility, the class was treated to a play put on by a group of inmates. This was a daunting experience, because while we were witnessing hardened criminals performing for us, the melancholy lurking beneath the surface of their production was palpable, particularly in how they all expressed sincere regret for the choices they made, and uniformly stated that they would have made better decisions knowing what they do now. It’s a memory that returns to me from time to time, especially when the conversation around prison reform and the inhumane conditions of many jails around the world weave their way into the discourse. This fits in perfectly with the discussion at the heart of Sing Sing, a film directed by Greg Kwedar, who wrote it in conjunction with Clint Bentley, basing it on the real-life Rehabilitation Through the Arts Programme started at Sing Sing Maximum Security Prison years ago, with particular focus being on the efforts of John “Divine G” Whitfield, who co-founded the programme while incarcerated for a crime he did not commit, using it as a way to not only filter his own frustrations and anger into a more productive form but also to give his fellow inmates the opportunity to experience the arts and how it can shift our perception and perhaps even change the lives of those willing to be dedicated to the process. The film is a semi-autobiographical account of Divine G’s efforts over the years, centring around a production he and co-founder Brent Buell staged, one of many designed to give willing inmates an effective and productive outlet for their personal issues, outlining the positive results such a process can have in genuinely offering rehabilitation to those who needed it the most, beautifully outlined in this stunning film.

The prison system is often considered to be broken beyond any hopes of recovery, and any attempt to reform it is only going to fall on deaf ears since it is far easier for those in power to lock up anyone who is deemed to have broken the law, rather than putting active effort into rehabilitating them and giving them the chance to change their ways. Films set in the prison system are not rare, and they run the gamut from callous, violent exploitation designed to draw on the terrifying nature of these institutions, to more intimate, insightful glimpses into the daily lives of both prisoners and staff. Sing Sing wholeheartedly belongs in the latter category, which is where it finds so much of its value, being a hauntingly honest look into the structures that maintain these facilities, and the many people who weave in and out of their usually squalid halls and have to face dehumanization treatment from those who are designated to keep them in line, rather than subject them to abuse. Kwedar has only worked on a small number of films and has his roots in non-fiction filmmaking, so it would make sense that he would have a vested interest in a more realistic examination of a system that is often ignored, very rarely being given this kind of tender, honest depiction that isn’t about reviling those who find themselves becoming a part of the institution, but rather serving to be a more tender, heartfelt voyage into the lives of these people as they serve their sentences, whether they are there temporarily or see their entire future being behind bars. Stories about prison have the challenge of walking a narrow boundary between exploitative and honest, and Sing Sing is crafted by a group of individuals who are wholeheartedly committed to telling the story as accurately and with as little judgment as possible. Kwedar involves many previous inmates of Sing Sing, including Divine G himself, who serves as a consultant and guides the narrative by providing insights into his life in prison, as seen through the perspective of those involved in a particular programme designed to give them both a creative outlet, and helps them find the rehabilitation they are desperately seeking, and which is expected from everyone who finds themselves forced to pay the consequences for their actions.

Sing Sing does not position itself as the definitive exploration of the prison system (it doesn’t even claim to be authoritative on the conditions within the titular institution), and presents only a small fraction of reality, which is only logical considering it is entirely impossible to craft a film that tackles every aspect of the lives of inmates and their experiences. To find the right approach, Kwedar works with both his creative partners and the subjects of the film to create a story that is based within reality, but focuses less on the actual events and more on looking at a particular set of themes. The primary one that propels this film is quite simply that of redemption – every person we meet in this film is seeking some kind of forgiveness, even those who are incarcerated for a crime they claim they did not commit. Something that is not often discussed in less-meaningful explorations of prison life is that one doesn’t necessarily only spend this time atoning for the crimes they are told they committed from a legal perspective, but also reflecting on their own choices outside of prison, seeking solace for decisions that may not be directly related, but still led them down the path that ultimately found them becoming incarcerated. This is where Sing Sing becomes so incredibly powerful, since it may be based on real people and events, but the underlying ideas are resonant. Every individual we encounter in this film is someone who has lived a life filled with bad decisions, and the regrets they feel have a painful lingering effect, reminding them of their failures as members of society. Yet, through a theatre programme designed to give them a platform to not only pass the time but to have their voice heard, gives them the chance to reconcile with their demons, find redemption within themselves. The film beautifully captures the feeling of coming to terms with your own choices, and finding the space to forgive yourself and move on – and while the bureaucracy may not always be compatible with this path of redemption, there is value in finding the ability to move on from a psychological level, and only after making the conscious decision to pursue the right path can one truly be considered entirely rehabilitated. It’s a sensitive topic, but Sing Sing uses every tool in its arsenal to tell this story in a manner that is honest and heartfelt.

Kwedar developed Sing Sing in collaboration with Colman Domingo, who stepped into the production and showcased his incredible passion for the material. As one of our greatest living performers, albeit one who has only recently started to get his due, Domingo is the perfect candidate to lead a film about the transformative nature of the arts, especially considering he has proven to be both a magnificent actor and a steadfast activist for various communities, both being badges that he wears with infectious, admirable pride. He takes on the part of Divine G and brings such incredible complexity to the role, which is particularly challenging considering he was not only playing a real-life person but also someone who was involved in the production of the film. Domingo’s performance is a masterful example of how subtle acting can be more effective than more bombastic styles – so much of this portrayal depends on non-verbal communication, with every expression and gesture carrying just as much weight as the spoken words, and which Domingo captures with a kind of sincerity that can only come from someone wholeheartedly dedicated to a story and its execution. He’s joined by Paul Raci, a veteran character actor plucked out of relative obscurity a few years ago with Sound of Metal, and who once again proves to be the epitome of empathy with this moving, earnest performance as the co-founder of the theatre programme and the de facto father figure to many of these participants. The rest of the ensemble cast consists of former prisoners playing themselves, a choice that is perhaps the most notable aspect of the entire film – Sing Sing prioritizes authenticity above everything else, and there is something truly incredible about giving these formerly incarcerated individuals the chance to tell their own story, rather than asking hired actors to attempt to capture the pain, despair and yearning for redemption present in these people. Domingo may be the star, but the beating heart of this film are these supporting players – Clarence Maclin (who has the biggest part of the real-life inmates), David “Dap” Giraudy and Sean Dino Johnson are just a few standouts, and bring so much heart and soul, giving every bit of themselves into a project wholeheartedly dedicated to telling their story with empathy and affection, which we find consistently throughout the film.

Considering how much of the attention directed towards Sing Sing has been based on the cast and what they bring to the story, we can tend to overlook just how incredibly well-crafted this film is, which is a testament to Kwedar’s wonderfully endearing approach that indicates how the form was just as important as the content of the film. The visual aesthetic on its own lends itself to a lot of praise – the gritty 35mm cinematography, coupled with the recreation of a prison facility that is relatively unfurnished and simple, creates the sense of a film plucked from a different era, one in which such storytelling was much more straightforward and focused less on the images and more what they represent. The brief bursts of colour are reserved for the theatrical performances, showing just how lively these inmates become once they can step out of the position of being felons, and instead take on fantastical and offbeat roles into which they can momentarily escape. Every decision made throughout this film – whether narrative or artistic – is intentional, designed to create a very clear atmosphere that focuses on the delicate balance required to tell this story. One of the more unheralded aspects of this production is how it explores its emotions – in the hands of a less compassionate director, Sing Sing would have likely been an overwrought, unnecessarily dense melodrama that is more focused on preaching its message than finding unique ways to examine these ideas. The benefit of having the real subjects involved is that the director was consistently striving for authenticity, and while it does have a few components that preclude it from being considered a work of social realism in the traditional sense, there is an authenticity to this film that is difficult to overlook. Every emotion in turn is engaging and meaningful and carries a sincerity that allows the film to be far more complex than its themes would have you initially expect. The director avoids making Sing Sing too overwrought and instead focuses on letting the narrative unfold organically, developing something deeply captivating from this simple but evocative material, which is both elegant and nuanced, as well as leaving an indelible impression on the viewer.

A simple but beautifully effective film that captures the most raw and honest emotions imaginable, Sing Sing is an incredibly moving work that may seem straightforward on the surface, but has enough depth and nuance to be a genuinely life-affirming testament to the arts, and how it can not only help someone work through their issues on the path to redemption, but inspire them to take their life into their own hands and change the narrative. The message at the very core of this film is that life is nothing but a series of stories we tell ourselves, and whether we perform them for the outside world to see, or keep them to ourselves, existence is simply the act of coming to terms with our personal quandaries and working through them in the best possible ways. It’s beautifully poetic, complex filmmaking that is filled to the brim with heart, and even the occasional burst of humour designed to add some worthwhile levity to an otherwise quite serious story. Kwedar is not a director who is known for challenging conventions, and perhaps the fact that the film has focused less on his vision and more on the real-life participants is proof of his immense empathy, as his position can be considered less of a person shaping this narrative, and more a shepherd that takes this raw material and facilitates the eventual conversations that examine the myriad of fascinating themes underlying this film. Anchored by a tremendous lead performance and a dozen exceptional supporting parts from a group of men seeking their redemption, even in post-prison life, Sing Sing is a beautiful and engaging film with as much complexity as it has soul, both of which exist in an abundance and guide this astonishing story forward, making it an essential work of contemporary social commentary.