Clarence Maclin never expected to recite Shakespeare as his job.

Growing up, Maclin liked to draw comic-book characters, and he briefly took up the flute. But these hobbies, picked up as a child in Mount Vernon, New York, in the 1970s were the extent of his artistic interests. “I just never thought about acting,” he says.

That’s hard to believe after watching Sing Sing, A24’s new movie about an ensemble of inmates at a maximum-security prison who start a theatrical group. Acting alongside his Academy Award–nominated co-stars, Colman Domingo and Paul Raci, Maclin, 58, shines in his feature-film debut as Divine Eye, a brooding prisoner who joins the troupe. He discovers a hidden talent—and affinity—for the stage.

Divine Eye’s story is partly based on Maclin’s own life experience. Growing up with a single mother and two younger brothers, he often got into trouble. “Childhood was rough for me, because we grew up poor,” says Maclin. Poverty pitted him against middle-class residents in his neighborhood. “I had to fight for my younger brothers. I had to fight all the time.”

Clarence Maclin in a scene from Sing Sing.

Maclin earned a G.E.D. in 1984 in lieu of graduating with his Mount Vernon High School class. “The next few years, I was on the streets,” he says. “I was taking money. That was my thing.” In 1995, at age 29, he was arrested for participating in a four-man armed robbery at a local grocery store. After a trial, he was convicted of first-degree robbery, among other charges. In 1996, he began a 20-year sentence at Sing Sing Correctional Facility, in Ossining, New York.

That same year, an organization called Rehabilitation Through the Arts (R.T.A.) was started at the prison by Katherine Vockins, a former marketing consultant. Her goal was to give prisoners an emotional outlet and foster the development of life skills through theater.

Maclin happened across an early R.T.A. performance. “It made me feel good in a way that I couldn’t really put a finger on, or explain,” he says. “I needed to get up there and find out what this was about.” To join R.T.A., Maclin needed to avoid receiving any “tickets,” or infractions, for an entire year. “That was really difficult for me, because I was always getting in trouble. But I did it.”

Though Maclin wasn’t given major parts at first, he immediately took to the productions. “I remember the feeling that once we got into this space—this room, with nothing but us in there—it was a different world,” he says.

Despite having never delivered lines—let alone soliloquies—prior to his conviction, Maclin starred in numerous plays, from Sophocles’s Oedipus Rex to August Wilson’s Jitney.

In Sing Sing, Maclin acts alongside Colman Domingo.

While the national recidivism rate is over 60 percent within three years of release, the rate among R.T.A. members is less than 3 percent. Maclin believes this is because R.T.A. “does not paint morals and principles on you. Rather, it draws them out of you.”

In 2012, Maclin was released from the correctional facility. Soon after, he began mentoring at-risk men with the nonprofit Lincoln Hall Boys’ Haven, in Westchester. He taught them many of the same acting exercises he’d learned from R.T.A.

In 2015, Maclin and his fellow R.T.A. members were approached about turning their story into a feature film. Brent Buell, a playwright who had worked with R.T.A. during Maclin’s sentence, and Greg Kwedar, Sing Sing’s director, were inspired by a 2005 Esquire article about the theater program. Maclin signed on immediately, even though he hadn’t performed since finishing his sentence.

The film, which premiered at the 2023 Toronto International Film Festival, has finally hit theaters. Maclin hopes that audiences “take away that the people in prison are exactly that: people. They’re human beings.”

While Maclin intends to act more going forward, he has to make time in his schedule. Maclin still mentors at-risk men, now with 914United, in Yonkers, New York. “Working with young brothers like me, I could realize exactly what they’re going through because I did it already.”

“Everybody has the ability to change,” he says. “Sometimes it takes more than two chances. Some guys just need a shot, and somebody to trust them, and trust that they’re going to do the right thing.”

Sing Sing is in theaters now

Jack Sullivan is an Associate Editor at AIR MAIL