Sing Sing: Where Prison Meets the Stage, and Hamlet Speaks

by Justyna Madenska

“There is nothing either good or bad, but thinking makes it so.”
(Act 2, Scene 2) Hamlet. William Shakespeare

When I watched the movie Sing Sing, I was captivated from the very first frame. It is so powerful that there isn’t a single moment where you can take your eyes off the screen. The words, the raw emotions of the people—it’s all laid bare, unfiltered, and undeniably real. You can feel the intensity of their experiences as they perform, making the connection between Shakespeare’s Hamlet and the prisoners’ own conflicts impossible to ignore. There’s a reason Hamlet was chosen for this story. Its themes resonate deeply within the prison walls and the lives of those trapped inside them.

We all know Hamlet as one of Shakespeare’s most famous plays, a masterpiece of tragedy filled with conflict, hesitation, and doubt. But doesn’t that sound familiar in a much more modern context? It’s the same emotional turmoil felt by many men and women who enter prison. They are thrown into a world of the unknown, grappling with inner conflicts, madness, and, ultimately, tragedy. It’s not just their personal tragedy, either. It extends beyond them, affecting their families, loved ones, and entire communities. Watching Sing Sing, I realized that the emotions in Hamlet—doubt, fear, confusion—aren’t confined to the stage; they’re a reflection of real life for many incarcerated individuals.

The film, which portrays the true story of prisoners at Sing Sing Correctional Facility in New York who participated in the Rehabilitation Through the Arts (RTA) program, shows how these men find a way to express their struggles through the power of theatre. What stood out most was how these individuals, who society often labels as hardened criminals, could so deeply embody the characters of Shakespeare’s play, especially Hamlet. Like Hamlet, they are conflicted, struggling with who they are and what they have done. They question their choices, their futures, and the forces that led them to this place. Their inner turmoil mirrors Hamlet’s famous soliloquies, where he wrestles with existence and revenge, paralyzed by doubt and haunted by the weight of his decisions. For many of these men, stepping onto the stage was not just about performing. It was an opportunity to confront their own demons, much like Hamlet’s confrontation with his father’s ghost. The uncertainty of their pasts, the madness that surrounds them in prison, and the consequences of their actions are all magnified under the spotlight. For those who have never experienced prison, this film offers a deeply emotional insight into a reality that is often hidden from the public eye.

Yet, what makes Sing Sing more than just a film about prison life is the humanity it brings to the forefront. The men in the RTA program are not just inmates; they are individuals trying to make sense of their lives. The emotions they pour into their performances are not simply lines from a script—they are expressions of the pain, regret, and hope that still exist within them. Just like Hamlet’s struggle to avenge his father’s death without losing himself in the process, these men are trying to find a way to survive and, if possible, redeem themselves.

The story of Sing Sing began with a 2005 Esquire article written by John H. Richardson. Richardson visited the prison to witness the RTA program firsthand, and what he found was both jarring and eye-opening. He watched men, convicted of serious crimes, nervously rehearse lines, laugh, sing, and perform. As Richardson saw the humanity beneath the prison labels, he noted the conflicting emotions of recognizing these men as individuals while knowing their past actions. “Shouldn’t these guys be punished?” he asked himself, before realizing the redemptive power of art.

What makes this movie so unforgettable is that Sing Sing isn’t just about the men in prison; it’s about the ripple effect their incarceration has on everyone around them. Their families are just as much a part of the story. The tragedy of prison life doesn’t stop at the prison gates. Mothers, fathers, siblings, children—they all live with the consequences, just as Hamlet’s actions lead to the downfall of nearly everyone he cares about. There is madness in prison, but there is also heartbreak for the loved ones on the outside, watching helplessly as their son or daughter disappears into a system that offers little room for redemption.

Sing Sing doesn’t shy away from this harsh reality, but it also reminds us that even in the darkest places, there is room for transformation. Theatre offers these men a way to confront their pasts and express their emotions in a way that few other avenues allow. And it reminds us of a simple truth: everyone, regardless of their mistakes, deserves a chance at redemption, a second act in the play of life.

Like Hamlet, the men in Sing Sing wrestle with their actions, their future, and their identity. It’s a story that stays with you long after the credits roll because it reflects a reality many of us are too afraid to confront. The film invites us to question our own beliefs about punishment, justice, and redemption. It shows us that sometimes, the most profound transformations happen when we least expect them, even in places where hope seems lost.

The driving force behind the RTA program is Brent Buell, an actor and director who devoted himself to helping incarcerated men and women find their voices through theatre. In the film, Buell is portrayed by actor Paul Raci, who embodies the compassionate, determined educator that sees potential in the prisoners when no one else does.

The film doesn’t just focus on the prison system’s failings or the grim reality of crime and punishment. Instead, it highlights the complexity of the human condition—the ability to change, to find light in the darkest of places, and to connect with others through shared creativity. It’s a powerful testament to the idea that no one is beyond redemption and that art can be a vehicle for that change.

As Sing Sing gains recognition for its heartwarming story, it brings attention to a broader conversation about the importance of rehabilitation in a society dealing with prison overcrowding and recidivism. While the film doesn’t delve into the perspectives of the victims’ families, it argues that separating a man from his actions is a step toward healing.

As I sat down to write this piece, my thoughts wandered beyond the confines of legal documents and into the realm of human suffering, hope, and perseverance. I’m not a journalist by trade, but a lawyer. Yet, in writing this, I found myself deeply moved, perhaps more profoundly than I expected. In a world where justice is supposed to be blind, we often find it distorted and corrupted. The case of Jon-Adrian “JJ” Velazquez is one such story—one of a wrongful conviction, a flawed legal system, and a man who spent nearly 24 years behind bars for a crime he did not commit. For decades, JJ Velazquez maintained his innocence, even as he languished in prison, wrongfully convicted of killing a retired NYPD officer during a robbery in Harlem. Despite shaky evidence, inconsistent witness testimonies, and his alibi—he was on the phone with his mother at the time of the crime—he was convicted in 1998 and sentenced to 25 years to life. But his story doesn’t end in despair. It’s a story of how the truth, no matter how buried, can eventually rise to the surface. And, it’s a story of the power of art and advocacy to bring about change. Despite years of legal battles, rejections, and disappointments, hope finally came in the form of clemency. On September 30, 2024, Velazquez walked out of prison a free man after spending nearly 24 years wrongfully incarcerated. The decision came after relentless advocacy from his legal team, the media, and activists who continued to fight for his exoneration. And in a rare and deeply significant gesture, President Joe Biden personally apologized on behalf of society for the grievous wrong done to Velazquez. The President’s words carried the weight of not only one man’s wrongful conviction but the broader issue of systemic injustice that continues to plague our legal system.

JJ Velazquez is not just a symbol of the failures of our criminal justice system—he is a testament to the strength of the human spirit. His journey is a reminder that even in the darkest of places, hope can thrive. There is power in advocacy, in never giving up, in speaking truth to power, and in finding ways to survive the unimaginable.

The film Sing Sing, which features real-life former inmates including Velazquez, brought his story to the world in a way that transcended the walls of the prison. The film became a powerful testament to the transformative power of art and the resilience of the men who participated in the RTA program. Watching the movie, it’s clear that these individuals are not defined by the crimes they were accused of or convicted for. They are human beings with stories, emotions, and the capacity for change.

Velazquez’s release marks the culmination of years of struggle—not just for him, but for everyone who believed in his innocence. His story underscores the urgent need for criminal justice reform and raises critical questions about how many others like him remain behind bars, wrongfully convicted or serving unjust sentences. It is a sobering reminder that while justice may be blind, it is not infallible. But at least in this case, after more than two decades of wrongful imprisonment, one man’s nightmare has finally ended. JJ Velazquez is free.

In conclusion, this film serves as a powerful reminder of the intricate and often precarious nature of life, akin to the themes found in Hamlet. It sheds light on the unsettling reality of wrongful convictions, emphasizing that anyone can find themselves entangled in such a tragic situation. By watching this movie, audiences are encouraged to reflect on the fragility of justice and the importance of empathy in understanding the human experience.

Sing Sing reminds us that no matter where someone is in life, the world is a stage, and everyone deserves a second act.

In the end, Sing Sing and Hamlet are both about the human condition—the choices we make, the consequences we live with, and the possibility of finding meaning in the midst of tragedy.