A Different Type of Prison Escape

Watching Sing Sing

This week I did something I have not done in ages—I went to the movies! I left work an hour early so I could escape the Florida heat by sitting in the cool darkness of a theatre, enjoy popcorn, and watch Sing Sing, a film about a theatre troupe in a maximum-security prison.  

Seeing Sing Sing at Green Light Cinema in St. Petersburg, FL

A Brief History of Prison Films

When I wrote my book, Prison Life in Popular Culture: From The Big House to Orange is the New Black (2015), I had to watch a lot of prison films. In the end, a classic, Cool Hand Luke (1967), became my favorite. It tells the story of Lucas “Luke” Johnson, who is sentenced to two years in a prison work camp for cutting the tops off of parking meters. His desire to escape is never thwarted, no matter how long they keep him in the box when caught. As a viewer you cannot help but to cheer him on throughout the film (a different reaction than some who have not seen a classic prison film may expect).

“What we’ve got here is…failure to communicate.” -Captain (Cool Hand Luke, 1967)

Prison films emerged in the silent film era and in the 1930s they entered their golden age. Early movies like The Big House (1930) established the conventions of the genre, which include an inmate hero, cruel guards, dangerous inmates, a fight for justice, and a riot or an escape.

The typical prison story follows a new inmate, who the audience believes is innocent or at least does not deserve the prescribed punishment. They watch him being processed into the prison, meeting his cellmate, and learning to navigate the prison social system while staying out of the path of the cruel guards. A riot or an escape is the plot device used to fight against the system.

In the 21^st century, these types of prison films have become less common. Instead, the prison is used as the backdrop for another type of story, such as revenge. In part because of this change, as well as how streaming services have changed the types of media I consume, I stopped paying attention to whether new prison films were being released. Imagine my surprise when I opened an email from Green Light Cinema and learned about Sing Sing, a film that made its debut the Toronto Film Festival in 2023.

Another Kind of Prison Film

Sing Sing is a moving story based on and featuring real men who have been incarcerated. Inspired by an Esquire article published in 2005, “The SING SING Follies” by John H. Richardson, it follows the men of RTA (Rehabilitation through the Arts) as they create and perform an original play featuring ancient Egyptians, gladiators, Freddy Krueger, and others, a task only possible via time travel.

A24 Films offer the following description of the film:

“Divine G (Colman Domingo), imprisoned at Sing Sing for a crime he didn’t commit, finds purpose by acting in a theatre group with other incarcerated men. When a wary outsider joins the group, the men decide to stage their first original comedy, in this stirring true story of resilience, humanity, and the transformative power of art, starring an unforgettable ensemble cast of formerly incarcerated actors.”

The outsider, Divine Eye, is similar to the newcomer in a traditional prison film; however, his journey is a different one. Viewers watch him leaving the mix (a term used to describe being ingrained in the game that is the inmate social system) and entering a place that has become a sanctuary for the group of men participating in the theatre program. In this role, Clarence Maclin, an RTA alum, plays himself. The film shows him struggling to leave the inmate code behind, which is the only way to escape and to transform. In frustration over his behavior in the group, another member of the troupe, Sean Dino Johnson (who also plays himself), tells him: “We’re here to become human again and enjoy the things that is not in our reality...” The theatre program is their escape.

The main character is Divine G (Colman Domingo), one of the few roles played by a professional actor. He is based on John Whitfield, another RTA alum who has a cameo appearance in the film. Divine G is an optimistic leader, who is fighting for his release. With evidence that he did not commit the crime for which he is in prison, he prepares for his clemency hearing, while trying to help Divine Eye change the way he looks at things, including the possibility of parole. In a traditional prison film we might call Divine G an inmate hero, but as we see in the film even heroes have bad days.

I do not want to say too much more about the film so as not to spoil it. If you are expecting to be entertained by cruel guards and animalistic inmates, violence in the yard, and a bloody riot or an ingenious escape, this is not the prison movie for you. But if you want to be exposed to a different type of prison story in which you see a way that those who are incarcerated find humanity and escapism within the confines of the walls of a prison, as well as the subtle forms of cruelty inflicted on those incarcerated by the system itself, then you should see it. Most of all, you should watch it to hear the stories of those behind bars and to see the incredible talent of the formerly incarcerated men featured in this film.