Sing Sing

Written by Andreas Babiolakis


Last year’s biopic, Rustin, saw one Oscar nominated Colman Domingo — a brilliant thespian who is finally getting his proper dues — having to do the heavy lifting by getting as raw as possible while everyone else around him played things safely. It felt like a wasted opportunity to see a modern day great showcase what he can do with the full, necessary support around him; what good is a film if only its central role is worthwhile? Heading into the new film Sing Sing — another Domingo-leading project from the festival circuit of 2023 (which is only getting its wide theatrical release now), we see the actor playing an actor mid performance: John Whitfield reenacting a scene straight out of Shakespeare. The set around him feels humble (with dangling, paper ornaments hanging from the rafters above, and a plastic crown atop his head), but he is giving the monologue his all, making us forget about the cheapness that he has elevated himself above. This felt like a reminder of Rustin and how special Domingo is: you hardly even care how off everything else is when he is this brilliant.

We cut away from this spellbinding opening opening shot to a stark reality; this is a performance taking place in the Sing Sing Correctional Facility in New York State. John is an inmate who has been there for years, and a small committee of fellow prisoners put on a new stage production for all the others every six months or so. It is seen as therapy for these men who wish to change as individuals, as well as a form of escape from the nightmarish conditions of a prison. While this film is all about trying to find new realities within the despair of being incarcerated, Sing Sing is actually rooted in pure truth. The premise of the film is that John is helping put together the latest production for Sing Sing, and it’s a weird mish-mash of ideas after a brainstorming session involving many unrelated desires. The end result is Breakin’ The Mummy’s Code: a story about an Egyptian prince who traverses through time and encounters Maid Marian, gladiator warriors, pirates, and Prince Hamlet, as he tries to fulfill his quest. Oh, and it’s supposed to be a comedic play. It seems insane, but Sing Sing is all about delivering honesty.

You see, Breakin’ The Mummy’s Code was a real play, conducted by members of the Sing Sing theatre community. This film is based on true events far more than you may even imagine; as evidence of changes-of-heart and a pursuance of the stage in the next phase of life, many of the actual Sing Sing actors appear in this very film as themselves. It is a sensational decision by director Greg Kwedar that leads to raw, unfiltered, humanistic acting in the way Italian Neorealism evoked similar performances. The Sing Sing program must be going very well when you watch these actors, especially when they appear so flawed and lousy on stage (and yet, while playing themselves, you could wear these men have been acting their entire lives); the dichotomy between the stage and real life is ever present within the film, and yet the film itself has completely blurred the art and the artists together and, in doing so, absolved these people in search of forgiveness of their pasts (Sing Sing never divulges what most of the inmates are in prison for, outside of the character of John who is revealed to be allegedly, wrongfully convicted as a subplot). They are allowed to start anew without our judgement.

Sing Sing places us within the titular correctional facility to understand the artistic therapy that acting brings to those who want to change themselves.

Sing Sing goes the extra mile with this premise, with a 35mm, cinéma vérité style that makes the entire feature feel like a documentary (because, in ways, it is one). How much of what goes on in this film and during this latest production being true is up to speculation (like the friendships that form, the drama that ensues), but that isn’t what Kwedar and company are interested in; they’re instead driven by the revelation of souls from society’s most hardened people as they embrace the world’s stage for all to see. If anything, we barely even see what comes from Breakin' The Mummy's Code, because the bonding during rehearsals is more informative than watching what transpired afterward. As we watch real inmates bare their spirits for the entire world, we know what art is capable of for the conveyor and the viewer; a connection that wouldn’t exist if the film tried to sell their story as plot fodder.

In the film, the acting program is directed by Brent Buell, played by Paul Raci, who is best known for his Academy Award-nominated turn in Sound of Metal. He is sublime here as he was in the previous film; while I would love to see him in a role that isn’t one of a mentor (to see the extent of what he is capable of), he is clearly great as one here, and I feel like both performances are different enough that they each revel different qualities of those who give up everything to try and inspire others to keep going. John is trying to help inmates in a similar way, particularly the gruff Clarence (a former inmate who, like many, plays himself) who has shown a passion for Shakespeare but feels that he cannot commit to fully diving into the acting world because he is too tethered to his past life of crime. He gives up on exercises and shrugs off suggestions, and this causes enough distress amongst the troupe that John and Brent can tell that such vitriol is unhealthy for this activity which is meant to soothe souls, not tear at them.

Sing Sing sees inmates acting as a means of escape. As a result, we enter their world for a little while to better understand them.

As the production is in need of funding and the big day is approaching, some fires get put out while others spawn. We see tables turn between characters, where some mentors are now in need of help themselves. Sing Sing is all about flipping the script, as it places us within the facility so seamlessly that we feel like we are a part of this experiment. We may forget that Domingo is already a superstar in the same way that we remain unconvinced that the inmates weren’t born to perform. We re-contextualize the drama program as a safe space within hell as we similarly worry about the outside world (given how exclusively the film takes place within the real facility); consider inmates who are granted the opportunity to leave Sing Sing as actors who are embracing the biggest stage of their lives (and showtime is near).

What helps this film soar is that Kwedar almost never gets ahead of himself and turns Sing Sing into the next sappy, artificial Hollywood film that forces you to feel sad. Outside of a couple moments of tension and emotion (which feel necessary when they happen), Sing Sing is as bare as possible. Despite being a film about an imaginative production, Sing Sing never forces us to see what is made. We are presented all that is necessary and are given the opportunity to form our own bonds and thoughts. If a prison can turn into the stage of a lifetime, so can our minds and hearts. Sing Sing is an effective experiment that cannot be shaken off. Its earnestness is much needed in the day and age of commercial project after commercial project. During a considerable lull in 2024, Sing Sing shines brightly as an exposition of art trumping falseness. It instills faith in us; that people can change for the better; that art brings people together during the ugliest times; that film will forever be rich with importance, inspiration, and beauty when handled properly; that there will always be brightness in the darkest moments.


Andreas Babiolakis has a Masters degree in Film and Photography Preservation and Collections Management from Ryerson University, as well as a Bachelors degree in Cinema Studies from York University. His favourite times of year are the Criterion Collection flash sales and the annual Toronto International Film Festival.