
The Oscar nominee gives a tender lead performance in Sing Sing, a moving picture that’s only held down by stale story structure.
It’s easy to forget the power of freedom. Be it physical, emotional, or creative, we can take for granted the potency that comes from fostering in a place where you can move, play, learn, and, hopefully, grow. As such, Sing Sing, the sophomore feature film of director Greg Kwedar (Transpecos), starts with a promising prospect: how can one find freedom while locked behind bars? Can one truly escape the confines of their imprisonment? If so, how long can you accept that illusion before reality forces you to come to terms with the bleak, harsh reality of your circumstances?
The answer, like all things, is fairly complex. And, either fittingly or ironically, Sing Sing itself is often caught between the confines of reality and fiction. Based on Rehabilitation Through the Arts, a real program found in Sing Sing Maximum Security Prison, the film incorporates real ex-cons and the prison actors-turned-screen stars that filled out this ensemble during their incarceration. Unfortunately, under the cumbersomely formulaic screenplay by Kwedar and Clint Bentley, Sing Sing sorely suffers from the moments that don’t live up to that honesty.
John “Divine G” Whitfield (Colman Domingo) must live inside his mind while stuck in an infamous maximum security prison. With the arts program, he allows other inmates to experience those same luxuries on the stage, including dear friend/collaborator Mike Mike (Sean San José). Enter Clarence “Divine Eye” Maclin (playing himself), a raw prisoner who often uses exaggerated personalities and convenient lies to get ahead in the yard. Divine G sees his potential and gets him to join the program. As stage director Brent Buell (Paul Raci) gears up another production, Divine Eye suggests doing something lighthearted. The result is a shambolic mess, but it seems infectiously fun for all involved. Meanwhile, Divine G unexpectedly becomes more in touch with his own burdens and his sense of security starts to crumble. When it becomes clear that freedom isn’t near, the walls start to close in.
The reel deal.

Filmed over the course of 19 days in various decommissioned prisons, Sing Sing prides itself in capturing an environment and atmosphere that feels rugged and richly realized. And through its eloquent 16mm photography by DP Pat Scola (A Quiet Place: Day One), Sing Sing finds a lovely poetic balance between the beauty in these grayed exteriors and sharp interiors. All while feeling as though you’re walking into corrupted correctional facilities that haven’t lost their hard-fought edge. Likewise, the cast (minus José and Oscar-nominated actors Raci and Domingo) features the prisoners-turned-actors who filled out this program during their time behind bars. It lends both a realism and the small-town play feel that makes the movie instantly endearing, even before you learn about the incarcerated characters.
And while a weaker film might’ve made the difference between the professional and the unprofessional actors more apparent, the ensemble seen here is never uneven. If it weren’t for the end credits, I wouldn’t have even realized how many of these performers were the real deal. Domingo, Raci, and José play well with these other actors, building them up and also giving them the freedom to showcase their individuality and world views accordingly. It is a credit to Kwedar that there isn’t a clear divide between the stars and the rest of the cast.
Still, the foundation feels inherently wonky. Once you learn more about G, where he’s been, and where he’s hoping to go, Sing Sing never quite captures the sincerity of his plight (despite it being based on a true story). The film’s structure seems oddly stuffy and rigid, as if it needs to adhere to an established style in order to seem more legitimate. It’s a shame because it’s the little moments where Sing Sing truly shines, when it’s unafraid to capture what it means to be inside and how that reflects on the characters’ internalized fight.
A no-holds-barred performance.

It has been such a thrill to see Colman Domingo’s rise over the last few years. With his stellar supporting turns in Zola, If Beale Street Could Talk, The Color Purple, and 2019’s Candyman, along with his recent Oscar-nominated performance in Rustin and Emmy award-winning turn in Euphoria. Domingo has firmly established himself as a performer to watch, and his star-turn here is just as compelling as you would expect from the intensely charismatic star. With his innate gravitas and warm presence, Domingo grows only more confident, more assured, and also refreshingly even more vulnerable and daring. His Divine G is as emotionally enriching as it is eerily eviscerating.
Even though Domingo is an actor who tends to go big and occasionally broad (as he did with Rustin) his star turn is an effective showcase because the film never feels overburdened by his persona. His aching, mesmerizing tenderness is emboldened by his unflinching willingness to play up the heartbreak and soulfulness of his character. He makes you feel every shuttered tear and reflective gaze. It’s a performance that deserves a big stage and a big screen, and his relishes the opportunity fully without making the show entirely about his turn.
It’s at once a giving and gratifying performance, one that continues to promise a vibrant, visceral career that will hopefully catapult one of our future A-list stars. You can feel his ascension, but as is the case with Divine G, he still needs to stay grounded, tattered to the here and the now. But, hopefully, it’s only a matter of time before Hollywood gives him more opportunities to fully excel.
The bottom line.
Sing Sing is an earnest, emotional drama that can’t help but be chained by its story limitations. Its attention to authenticity in terms of recapturing the real circumstances and the real sense of community found in confinement is certainly admirable, and it does bring a vibrant and harrowing weight to the screen. Through an invigorating performance from Domingo and a talented ensemble of both new and familiar faces, Kweder’s fervent second film is only moderately shackled by its faults.
Sing Sing is now playing in select theaters. You can watch the trailer here.
Images courtesy of A24. You can read more reviews by Will Ashton here.
REVIEW RATING
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Sing Sing - 7/10
7/10








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