The Soft Beauty of “Sing Sing”: A Must-See Human Film

Coleman Domingo and Clarence Macklin star in Sing Sing, a prison film that serves as a tender reminder of our shared humanity.

1. The Performances

Sing Sing is about a theater group at one of New York’s most notorious maximum-security prisons. Within these hallowed walls, a group of incarcerated men gets the opportunity to perform. The cast, led by the dynamic Coleman Domingo, portrays men yearning for an escape—a moment of humanity that allows them, even if just for a moment, to feel free.

The performances are stellar. Most notably, Clarence "Divine Eye" Maclin, a formerly incarcerated actor, plays a version of himself. He, along with Coleman's character, Divine G, crafts a heartwarming and ever-changing portrayal of Black male vulnerability rarely seen on screen.

Each moment matters. Every conversation is an exploration of the fight to be seen and respected—a struggle many Black men face, whether bound or free. Along with the rest of the cast, many of whom play versions of themselves, they all find moments of softness that allow their humanity to shine through.

Each performance deserves a round of applause.

2. The Writing

Within the walls of the prison are myriad stories, some harrowing and others humorous. The screenplay, which took roughly six years and numerous page-one rewrites, was beautifully crafted by screenwriters Clint Bentley and Greg Kwedar.

What’s more impressive is the depth and authenticity of the language, as well as the well-structured screenplay that continually raises and redefines the stakes, making us feel hopeful one minute and completely hopeless the next—a daily refrain for our brothers and sisters caught in the prison industrial system.

Even though the writers don’t share the cultural context of the characters they portray, the common thread of humanity and Black male intimacy they’ve injected into this project is profound.

After struggling with the script and the dearth of characters, they enlisted the help of Macklin and opened up the process. From it, they’ve created something necessary to add to the film canon that features Black men in lead roles.

Bravo!

3. Big Questions Are Asked

At the center of the story lies a powerful theme that asks: Are we acting?

On its face, the question might not seem profound, but the exploration of this narrative in Sing Sing certainly is. Prisons are microcosms of the worlds we live in. 

As with every environment, survival is key. The stakes are raised according to the mission, danger, or purpose.

As the film goes on, the question becomes bigger, eventually leading us to a deeper contemplation of the idea of acting—pretending. For Black creatives, the idea of pretending is often a determining factor in who we work with and the environments in which we either shrink or thrive, because “pretending” is exhausting. 

At our core, we seek the safety and exploration the prison group in the film created for one another.

A space of forgiveness. A space of truth. A space of freedom.

What if Hollywood was that place? What if Hollywood didn’t force us to act?

What if. 

4. White Filmmakers (Properly) Shape a Black Narrative

I think this is important to witness. As I watched the film, it was more than apparent to me that a Black screenwriter had to have been involved. Bottom line: They got it right.

I was gobsmacked to realize this was not the case. However, after watching Clint Bentley speak about the construction of the screenplay on Film Courage, it showed me the beauty of collaboration. He stated that it was only when they opened the door to the process that the script was able to thrive.

That’s an important underlying narrative about this project. Mostly explored through group sessions, Sing Sing showed that community was the great equalizer.

With the skill of the writers to understand structure, motifs, and theme—combined with Mackin’s lived experience and knack for rich dialogue AND incredible acting—they created a safe space for everyone to thrive. 

The success of the picture proves that if more Black creatives were invited behind Hollywood’s closed doors, we could benefit the world and do what film was designed to do: change how you see the humans you don’t know.

Sing Sing is a powerful, rich film experience that should be seen by all. There’s no way possible to leave this experience unchanged, unless you choose not to participate. 

Welcome to The Mainstream!