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TIFF 2023 Review: ‘Sing Sing’ Focuses on the Realities of Incarceration

TIFF 2023 Review: ‘Sing Sing’ Focuses on the Realities of Incarceration

Whenever I read a headline about a long standing ovation at a screening, I usually chuckle and shake my head. But on Sunday, at the screening of Sing Sing, I was one of those people. I stood, cheered, and clapped for four whole minutes at this brilliant film and the people who made it. I also cried at the end. What an absolutely amazing, emotional film. Director and co-writer Greg Kwedar really created something special.

Watching Sing Sing at TIFF was a whole experience. The film itself was one experience. The follow-up was the opportunity to see Colman Domingo and five of the thirteen cast members who were formerly incarcerated and real-life rehabilitation program alums on whom a play in this film is based. Their presence on that TIFF stage and their response to the Q&A was an eye-opening experience that further increased the film’s value. Learning that these formerly imprisoned men received travel visas from the Canadian government just two days before the film was set to screen at TIFF showed the determination and tenacity of the cast and crew of Sing Sing

Based on the real-life arts rehabilitation program founded at Sing Sing Correctional Facility, Kwedar’s film is about a theater troupe at the facility in New York who find escape from the harshness of their realities of incarceration through Rehabilitation Through the Arts (RTA). The men work on a play and perform it for the other people in prison and for those on the outside who come in to view it. 

Every six months, the men gather to help decide their next play, looking to Divine G (Colman Domingo) to lead the efforts. When Divine G recruits a new member called Divine Eye, played by the real Clarence “Divine Eye” Maclin, he gets more than he bargained for. The group dynamics shift when Divine Eye suggests they do a comedy this time. Ancient Egypt, Freddy Krueger, and Hamlet find themselves in the same play. 

Through this theater troupe, we see the discomfort and vulnerability of these men. We also see the formation of trust and integrity as they work as a team. The film highlights the bond that develops between the men.

You would think all of these men who played themselves in Sing Sing were professionally trained actors. They are able to go toe to toe with the uber-talented Colman Domingo and give audiences a memorable performance. The man that surprised us was Maclin (Divine Eye). The chemistry between him and Domingo was strong. You could tell this was a bromance for life. Other cast members included Paul Raci as Brent, Sean San Jose, Sean “Dino” Johnson, Jon-Adrian Velazquez, David J. Giraud, and John “Divine G” Whitfield. There is a genuine authenticity in the performances on screen. It blurs the line between reality and narrative. It was a beautiful fellowship to see.

The writing of this film should be applauded. Kwedar and his filmmaking partner, Clint Bentley, have given us something special. The two of them volunteered as teachers in RTA and eventually developed this story with the men whose lives are shown. There are clear themes and messages about the stigma behind incarcerated people. What shines through is the story of who these men are, what they are capable of, and what they have to offer. There is power and beauty in the theater, in the arts in general. Sing Sing gives us a small glimpse of these men’s journey to get where they are. These are stories that matter with a focus on community and resilience. Coupled with the direction of this film, Sing Sing is charming and compassionate.

An interesting thing about this film is its commitment to film in a location that serves the story. The filmmakers could have easily had a set built, but the crew, led by producer Monique Walton, chose to film in three locations. Anterior scenes of Sing Sing were filmed highlighting the commuter train line that goes through the yard and the juxtaposition of the sprawling hills and Hudson River amid razor wire and chain link fences. Sing Sing was shot in a decommissioned Downstate Correctional Facility (a maximum security prison), the theater in nearby Beacon High School, and a one-time boys’ correctional school, the Mid-Orange Correctional Facility — now the Hudson Sports Complex.

Sing Sing highlights the prison system and its efforts to break down a person to “make them into a subservient machine.” The cast and crew show us how theater can put people back together and allow them to discover who they are. On screen, through these performances, we can see the rediscovery of empathy and adjusting outlooks on life. It’s beautiful.

Seeing Sing Sing and learning as much as I did about the people and the program was an honor. I hope other audiences get as much out of it as I did.

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