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Based on the Rehabilitation Through the Arts (RTA) program that began at New York’s maximum-security Sing Sing Correctional Facility, inmates stage theatre productions for their fellow prisoners.Dominic Leon/Elevation Pictures

Sing Sing

Directed by Greg Kwedar

Written by Clint Bentley and Greg Kwedar

Starring Colman Domingo, Paul Raci and Clarence (Divine Eye) Maclin

Classification N/A; 105 minutes

Opens in select theatres Aug. 2

Critic’s Pick

Last year, actor Colman Domingo brought two world premieres to the Toronto International Film Festival: the Netflix civil-rights biopic Rustin, and the independently produced prison drama Sing Sing. (Well, technically Domingo was there only to promote Sing Sing, given that the technicalities of the SAG-AFTRA strike prevented him from discussing any project from a major studio or streamer.)

While the lightweight and flawed drama, Rustin, went on to earn Domingo a long-deserved best actor Oscars nomination, it is Sing Sing that truly rattled TIFF audiences. And when it finally opens in Canadian theatres this weekend, it will be Sing Sing that will, or should, push the actor’s name into the brightest of marquee spotlights for the foreseeable future. This is as big, immersive and knock-down-drag-out impressive a vehicle as any leading performer could possibly hope for. And Domingo makes an absolute five-course meal out of it.

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Mixing professional actors such as Domingo alongside real-life alumni of RTA, Sing Sing plays with notions of authenticity in a sincere and sensitive manner.Elevation Pictures

Based on the Rehabilitation Through the Arts (RTA) program that began at New York’s maximum-security Sing Sing Correctional Facility, in which inmates stage theatre productions for their fellow prisoners, the new film from Clint Bentley and Greg Kwedar is a captivating experiment in progressive docudrama.

Mixing professional actors such as Domingo alongside real-life alumni of RTA, Sing Sing plays with notions of authenticity in a sincere and sensitive manner, with the ultimate goal to find and highlight the aching humanity that lurks behind the coldest and harshest of physical (and metaphorical) walls.

Domingo stars as John (Divine G) Whitfield, a real-life RTA alum and literary buff who, while in prison, used his time to mentor younger men in the liberating art of performance and storytelling. Whitfield’s latest mentee is Clarence (Divine Eye) Maclin, a real one-time inmate who here plays a younger version of himself: a cocky trouble maker whose raw talent for the stage is often sabotaged by his fiery temper.

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A cautious but ambitious approach helps Sing Sing consistently stay one step ahead of dramatic implosion.Elevation Pictures

Together, Maclin and Domingo’s Whitfield help stage a wild original musical called Breakin’ The Mummy’s Code – which features everything from ancient Egyptians to Hamlet – that the RTA group put together under the supervision of playwright Brent Buell (another real-life figure, played here by veteran character actor Paul Raci).

As they did on their 2021 film Jockey, Bentley and Kwedar – who trade off writing and directing duties and credits every other production – blur the borders between documentary and dramatization, injecting so much real-world history and personalities into their narrative that the whole thing threatens to burst at the meta-contextual seams. Yet the pair’s cautious but ambitious approach – an equal balance of grace and gratitude – helps Sing Sing consistently stay one step ahead of dramatic implosion.

Even the most tremendously assembled drama, though, needs a beating heart at its core. Which is where Domingo comes in, keeping the entire production pumping so fast that audiences might get emotional palpitations. The way that the actor is able to nail Whitfield down in moments so small and so large is nothing short of a magic act. Domingo’s eyes at once scream bottled-up rage and undying hope.

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Colman Domingo stars as John 'Divine G' Whitfield, a real-life RTA alum and literary buff who, while in prison, used his time to mentor younger men in the liberating art of performance and storytelling.Elevation Pictures

By this point in his life, Whitfield can do little but keep his expectations and hopes for his future rock-bottom low. The man comes alive, though, every time he opens the page of a script, catches the audition of a fellow inmate, or sees the potential in Divine Eye’s raw talent. Domingo swims into this complicated swamp of emotions with subtle, sharp ferocity.

And yet, the great trick of Sing Sing is that for all of its leading man’s virtuoso professionalism, the actor never blows any of his amateur co-stars out of the water. They are all of a piece, fitting together into a scrappy but lovingly assembled puzzle. Like the members of the actual RTA programs, they want nothing more than to put on a good show.

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