The Real 'Sing Sing': A Maximum-Security Prison that Puts Incarcerated People Center Stage

Rising above the Hudson River in the quiet town of Ossining, N.Y., Sing Sing Correctional Facility has long loomed large in the American imagination. Built in 1826 when the nation was still experimenting with how to punish and reform, the prison quickly became a byword for confinement. The phrase being sent “up the river” for incarceration was inspired by Sing Sing’s riverside location.

The prison’s fortresslike walls and narrow cells reflected the 19th-century belief that discipline, isolation and hard labor could cleanse the criminal spirit. Visitors came by the thousands to see the “House of Fear,” drawn by equal parts curiosity and dread. For generations, Sing Sing’s name evoked fear and finality. But the acclaimed 2023 film Sing Sing tells a different story—one born inside these same walls, where a group of incarcerated men found hope and humanity through performance and art.

For much of its nearly two-century history, Sing Sing housed some of the nation’s most dangerous incarcerated individuals, including serial killers David Berkowitz (aka the Son of Sam) and Albert Fish. For decades, it was home to “Old Sparky,” New York’s electric chair. More than 700 people were executed by electric chair at Sing Sing, including convicted spies Julius and Ethel Rosenberg, before the state abolished the death penalty in the 1960s. 

Life inside was harsh and rigidly controlled. Early inmates quarried the stone used to build their own cells. Silence was mandatory; a whispered word could bring solitary confinement. By the mid-20th century, prison reform efforts had softened some of the most brutal practices, but Sing Sing remained one of the nation’s toughest maximum-security prisons. Its population swelled with men serving long sentences for violent crimes.

Yet even within its grim walls, there were flashes of humanity and attempts at rehabilitation. Educational and vocational programs taught reading, carpentry and other trades. In the 1980s and 1990s, new initiatives began focusing on emotional and creative expression. 

In 1996, a volunteer organized a theater workshop at Sing Sing with a small group of inmates. Over the next several months the group worked to write an original play, which premiered the following year. The play’s success inspired the creation of Rehabilitation Through the Arts (RTA), a nonprofit launched inside the prison.

The idea was simple but radical: Theater, writing, dance and music could help incarcerated men find confidence, discipline and empathy. Over time, RTA expanded to several other New York prisons and became a model for how the arts can change behavior and reduce recidivism.

Inmates wrote scripts, built sets and performed for audiences: other inmates, family members and staff. Participation was voluntary, but those who joined often described it as life-changing. Through rehearsals, they learned to listen, collaborate and express emotion—skills that traditional prison life discouraged.

As one RTA member noted, “Art allows you to think differently, so you behave differently, so that you can get different results. To me, that’s the definition of rehabilitation.”

RTA’s impact has been striking. Participants are far less likely to return to prison after release, and disciplinary infractions among active members are rare. More importantly, it has reshaped how both inmates and staff view what’s possible.

That transformation of men finding identity and dignity through art became the heart of Sing Sing, the 2023 film directed by Greg Kwedar and starring Colman Domingo. Based on the true story of RTA’s founding, the film featured several real program alumni, including Clarence Macklin.

Domingo plays Divine G, a composite character inspired in part  by John “Divine G” Whitfield, an RTA member serving time at Sing Sing who later helped bring the project to life on screen. Rather than portraying inmates as faceless or broken, the film shows them as complex men using creativity to rebuild their sense of purpose. Inmates improvise, joke and console one another as they mount an original play inside the prison theater. The result is tender and deeply human—far from the violent images typically associated with maximum-security prisons.

Critics praised the film not only for its artistry but for its authenticity. Filming took place at several decommissioned prison facilities. For audiences unfamiliar with the program, the movie offered a rare glimpse of a world where art and confinement coexist. The film was shown at more than 1,000 correctional facilities across the country and earned three Academy Award nominations, including Best Lead Actor for Domingo. 

Nearly 200 years after the first inmates quarried its stones, men still wake each day behind its walls. But now, some of them also step onto a stage, reciting lines that tell their own stories. For some, Sing Sing is a rare example of hope in a system often defined by despair. For others, it’s a reminder that meaningful rehabilitation still reaches only a small fraction of the incarcerated population. Either way, the story of Sing Sing, both the real place and the on-screen version, captures the contradictions of American justice. It is a place built for retribution that has, through art, found glimpses of redemption.