Sing Sing (2024)

Dir: Greg Kwedar

Cast: Colman Domingo, Clarence Maclin, Sean San Jose, Paul Raci

It may not have had the emotional impact I was expecting but this heart-warming true story is undeniably an inspirational exploration of art and redemption

Throughout cinematic history, there has been an abundance of inspirational and occasionally gut-wrenching tales revolving around the American judicial system. These range from feel-good, tales of survival , such as “The Shawshank Redemption” (1994), to the almost farcical sports drama “The Longest Yard” (1974). One habitual trait that these thematically diverse prison dramas often have in common, is that they are often subject to customary Hollywood cliches. Even when prison-set dramas are based on, or inspired by, true events, they frequently fall victim to melodrama as a result of typical industry convention.

I was hoping that this would not be the case with the aptly titled “Sing Sing”, a real-life prison drama that first premiered at TIFF back in 2023. Inspired by the Rehabilitation Through the Arts (RTA) programme that ran at the titular Correctional Facility in New York, “Sing Sing” follows several incarcerated individuals who seek either redemption or escapism from their past crimes, through the medium of theatre and the arts. Writer-director Greg Kwedar and screenwriting partner Clint Bentley began production on the film in 2022 having acquired the rights to an Esquire article entitled “The Sing Sing Folies” back in 2005. It was announced prior to filming that the majority of the small ensemble would be made up of previously convicted actors, some of which having previously taken part in the inspirational rehab programme.

Since its premiere over a year ago, “Sing Sing” has garnered universal critical acclaim, and despite a surprisingly limited release throughout the United States in the summer, it has garnered enough attention to warrant award season buzz. This strong early word-of-mouth saw “Sing Sing” become the early Oscar frontrunner for the upcoming awards in March, and despite having fallen out of favour, largely due to its limited release and subsequent low box office returns, it is still expected to land a Best Picture slot when the nominations are announced on Friday 17th January. As a result of the limited worldwide release by distributor Black Bear, it was difficult to track the movie down in cinemas in the UK also, but now at the start of 2025, sixteen months after its premier at Toronto, I have finally managed to watch “Sing Sing” on video on demand.

Leading the cast of formerly incarcerated men is the movie’s biggest star, Colman Domingo. Having seen his own stock rise significantly in recent years following lauded performances in “Ma Rainey’s Black Bottom” (2020), “The Color Purple” (2023) and “Rustin” (2023), the latter of which landing him an Academy Award nomination, Domingo stars as Divine G, a convict currently serving time at Sing Sing for a crime he did not commit. Divine G discovers a sense of purpose through participation in the RTA, where he emerges as star performer and playwright alongside theatre director Brent Buell (Paul Raci). As the group prepares for their latest production, Divine G recruits talented but aggressive inmate Clarence “Divine Eye” Maclin (Himself), and the two immediately clash over the production, as well as the meaning behind it, with the more cynical Divine Eye dismissing the programme’s transformative nature.

Over the following weeks, the two inmates and their fellow performers begin to bond as they prepare for their production, a farcical comedy adaptation of Hamlet involving time-travel, pirates and Ancient Egypt. Divine G excels effortlessly in his exercises, inspiring his fellow performers, including close friend and cell neighbour, Mike Mike (Sean San Jose). Meanwhile Divine Eye struggles to connect with his emotions, having put on a tough guy persona for the majority of his serving time, by constantly brandishing a blade and demanding drug money from fellow inmates. Divine G is determined to get the production over the line, as well as proving his innocence to get his freedom.

Even though it shares similar thematic elements to other prison dramas, largely focusing on character arcs of emotional growth and redemption, “Sing Sing” cleverly avoids the trope of becoming melodramatic. Thanks to Kwedar and Bentley’s extensive research into the real life participants of the RTA programme, there is a genuine feel of authenticity here that is refreshing in a prison based drama. This is further complemented by cinematographer Pat Scola, whose decision to film on 16mm, results in a documentary-style aesthetic. Scola uses the oppressive nature of the prison environment to his advantage, cleverly mixing the cold natural lighting within the prison itself, with the warm undertones seeping in through the many windows that constantly remind the convicts of the outside world that they can see, but not explore.

The real life story of the RTA programme is truly inspirational, and “Sing Sing” is undoubtedly at its strongest when it explores how the performing arts can help reshape and rehabilitate even the most troubled individuals. This sense of hope, or even psychological freedom, is embodied through Clarence Maclin, playing a younger version of himself, having taken part in the theatrical project in real life whilst he was incarcerated in Sing Sing for armed robbery. Maclin is outstanding in the role, a true breakout performance, which further proves how impactful the RTA programme must have been for those involved. My one issue with the narrative however, is the initial central conflict between Maclin and Domingo’s character Divine G. The dynamic between the two morally incompatible characters was believable enough, but their subsequent resolution seemed to be rushed, partly due to the movie’s short runtime of just under 100-minutes. I found myself not as emotionally impacted as I would have hoped by the time the narrative reaches its conclusion, and it is the all too fleeting emotional interactions between the ensemble that lessens any gut-punch the film attempts to land.

Luckily, working in the film’s favour is the ensemble itself, with every performer appearing to be in their absolute element. The real-life ex-cons provide the beating heart alongside the more immediately engaging Maclin, while seasoned professionals Domingo and Raci rely on all their experience to help guide their lesser known cast members through the film’s dramatic and occasional comedic moments. Domingo has established himself as one of the most influential performers currently working in the industry since his own relatively recent breakthrough, and the Academy Award-nominee’s fantastic ability to convey emotion through subtle facial cues, as well as delivering explosive, scene-stealing monologues, is ultimately what helps propel the film’s narrative.

While I was somewhat disappointed by not having my heartstrings tugged to the extent I would’ve hoped, Greg Kwedar sophomore feature remains one of the most inspirational releases of the year.

Sing Sing is now available to watch on video on demand

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