Sing Sing Review – TIFF 2023

“To Become Human Again”

Sing Sing
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Sing Sing

Brutalist Review Style (Version 2)

I am minutes out of the Sing Sing screening at TIFF 2023; saying I am impressed is an understatement. I went into the film with limited knowledge, just wanting to enjoy an interesting movie. I knew it was a true story, but like most films, I assumed a lot of liberties were taken for the sake of entertainment. It wasn’t until the credits rolled that I realized most of the actors in Sing Sing were playing themselves. This is a true story portrayed by the people who lived it.

Sing Sing is the story of a program called Rehabilitation Through the Arts (RTA) at Sing Sing prison. We follow John “Divine G” Whitfield (Colman Domingo) during his time as a founder of the program alongside the program’s director, Brent Buell (Paul Raci). RTA is meant to create a space for prisoners to learn to feel, connect and communicate. As said by one of the men in the program, “We here to become human again.”

“We weren’t watching men survive ‘prison life,’ we were just watching them survive real life…”

Directed by Greg Kwedar, Sing Sing opens with a close-up of Divine G performing Shakespeare. Framing like this is used throughout the film to bring us closer to these men. We see them again during auditions as each man is introduced. We instantly learn who is funny, who’s fierce, who’s hurt. Kwedar found ways to let us into their minds without needing them to speak.

At one point in the film, the music is almost uncomfortable to listen to as the volume increases and fills with high-pitched screeching. This is right when we see Domingo’s character beginning to break. Piece by piece, he grows colder and more broken. Kwedar masterfully puts this on display with minimal dialogue. Pairing his direction with the unbelievable amount of expression in Domingo’s eyes alone, entire scenes can be played out with ease.

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I found myself falling in love with some of the characters long before I knew they were, well…themselves. Carmine is a 71-year-old man talking about loving and missing his wife. My note to myself was, “I want that love.” Another man with face tattoos auditioned to play a psychopath, and though it should have been a tad concerning, I adored him right away. Mike Mike, though, is where we start to find out that there is true humanity in these men.

Divine G always feels different than the other prisoners. He is well-spoken, well mannered and educated. He loves the arts. His cell is filled with books and a typewriter, things an intellectual would have, but he never for a second believes he is better than anyone else. Domingo’s ability to bring this to life without making him feel stuffy or elitist is excellent. Watching his character’s relationship with men who seem so different from himself is something more people should be taking note of.

Throughout Sing Sing, I was constantly waiting for a tragedy. I was waiting for someone in the program to ruin it for the rest. I was waiting for a violent crime if I’m honest. Though there are absolutely ups and downs, I was surprised with where they came from and how they were handled. We weren’t watching men survive “prison life”, we were just watching them survive real life, and all the things that come with that: life, death and even moms.

When we see our now actors with costumes and props, we see almost childlike behaviour. One man notes he hasn’t seen himself in a suit in 15 years, and some are running around with fake swords. We even see them pushing each other around in a laundry cart decked out like a boat. RTA brought humanity to men who thought they lost it. It brought skills they would have never had, including confidence and faith in themselves.

I think the most meaningful metaphor to me was Divine G playing Goliath. “Never fear, Gladiator Goliath is here!”. Divine G was a saviour to many of these men, in and out of the program. He pushes them to be better, helps them with parole, and convinces them not to give up after certain events. In the Q&A, Maclin noted that prison won’t rehabilitate anyone; they have to be willing to rehabilitate themselves, and that is what Whitfield helped other people do during his time at Sing Sing and continues to do today.

Sing Sing is a poignant look at brotherhood and humanity in a world where our justice system looks to lock away rather than rehabilitate.”

A minimal complaint from me would be some issues with pacing. The relationship between Whitfield and Maclin starts off tense. Divine Eye is resistant to the process, and Divine G really doesn’t seem to have faith. It feels like, in one scene, they decide to get over it and become fast friends, almost like we are missing a scene somewhere to see that turning point. Outside of that, every relationship really serves a purpose and feels genuine.

Sing Sing is a poignant look at brotherhood and humanity in a world where our justice system looks to lock away rather than rehabilitate. With Kwedar’s skillful way of delivering audiences into the minds of these characters without a word and how real they genuinely feel (because they are), makes Sing Sing a must-watch at TIFF 2023.

To learn more about the Rehabilitation Through the Arts program, visit

Final Thoughts

Dayna Eileen
Dayna Eileen

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