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Colman Domingo first met Clarence Maclin on a Zoom call in 2022. Domingo’s slate that year included playing Mister in the remake of The Color Purple and the title role in Rustin, a biopic about Civil Rights activist Bayard Rustin that would earn him an Oscar nomination. Maclin, by contrast, was a decade out from serving his sentence of 15 years in New York’s notorious Sing Sing prison for robbery. “We started talking about the bonds of brotherhood that Shakespeare illuminates,” says Domingo. Shakespeare, they agreed, was key to the film they were about to make together.
Sing Sing, director Greg Kwedar and co-writer Clint Bentley’s prison-set drama — more than eight years in the making — first screened to rave reviews at the Toronto Film Festival in 2023. Now, after a slow build, it is a buzzy Oscar contender. Domingo plays John Whitfield, A.K.A. Divine G, a leading force in the prison’s theater group, supported by New York’s Rehabilitation Through the Arts (R.T.A.) program. Maclin, known since his youth as Divine Eye, plays a reworked version of himself; he’s the hard man of the exercise yard. It was the real G who persuaded him to join the theater troupe which, he says now, made it possible for him to turn his life around.
Kwedar read about the R.T.A. when he was working on a documentary in another New York state penitentiary, Green Haven. The organization had been helping prisoners put on plays since 1996. It seemed to work — the recidivism rate for R.T.A. alumni was 3%, compared with an overall rate of 60% — but what really inspired him was an Esquire magazine account of one production, “a time-traveling musical comedy” called Breaking the Mummy’s Code.
That play, written with the prisoners by professional director Brent Buell, had everything from zombie mummies to Freddy Krueger. “There was something about the playfulness of the work juxtaposed against its environment,” Kwedar says. “The joy of the process that just leapt off the page. I wanted to experience some of that joy myself.”
He contacted Buell, who had stayed in touch with many of the old Sing Sing gang. Buell invited Kwedar and Bentley to meet them over breakfast. “Around that table, there was just a special energy,” says Kwedar. “Just the camaraderie, the New York accents, the humor, the deeper vulnerability. And we were just like, ‘If we could just take how this feels and put it in a movie we’d have something.’” He started working with the R.T.A. himself as an acting teacher; meanwhile, he and Bentley labored over the writing.
For years, it wasn’t working. What they should have done, they realized, was work the same way the theater group did. “We needed to open up our writing process,” says Kwedar. “It couldn’t be so traditional. Because we were making a movie about a community, and so our process needed to embrace that mindset. And so, the real Divine Eye and Divine G came into the storytelling process with us at that point. And immediately it was alive on the page in a way it just never had been before.”
The Sing Sing cast includes 13 former prisoners and three professional actors. Everyone, including all the crew, were paid the same. On one corner of the script, Kwedar had written the words “Colman Domingo”, not expecting that bit of dream casting to come true, but Domingo jumped at it. He wanted all of it — the flat payscale, the mix of professionals and R.T.A. alumni, the themes, and the fact that Kwedar wanted him to bring every skill he had: writing, producing and directing as well as acting. “They really asked for everything of me, and I gave it all,” says Domingo. “Leading the film, and finding the soul of the film, and highlighting these men who are usually not examined in their fullness. And because I’m with those men, I thought I can’t just put on a performance. I have to bring a bit more of myself.”
Above all, he brought the positivity that illuminates Divine G’s sad story. The real John Whitfield struggled for years to prove he had not committed the crime for which he was jailed. The parole board rejected his appeals repeatedly but, as the film shows, he never gave up trying. Domingo found a parallel with his years when he was struggling and penniless, long before he became a leading theater actor, star of Euphoria and Oscar nominee. There were dark years.
“When I learned that about him, I thought, Oh, I understand that man. I understand him deeply,” says Domingo. “And that’s the part of myself that I brought to this film. What happens when things are hopeless or dire? I’ve had those moments where I didn’t have money, or success. I guess the answer that you need to sort out in your soul is: what keeps you going? And I kept going because of faith, believing that there was something for me.”
He never interviewed the former prisoners or asked direct questions. “Instead of interrogating them about their experience, I just said, ‘Let’s sit and have lunch.’” Maclin describes it as a “subtle enfolding”, saying that he seemed simply to absorb the real Divine G until he began to look like him. “You’d be looking out of the corner of your eye and catch a glimpse of Colman, and you’d swear that was Divine G. And he did a lot more listening than talking, when he could have come in, like, big. He’s Colman Domingo!”
Neither of them sees Sing Sing as a prison movie. It doesn’t deliver the clichéd shocks of a conventional prison drama: there are no stabbings in the shower block, no rapes in the corridor. If anything, it is more like one of those Judy Garland-Mickey Rooney films where a bunch of kids put on a show. For Domingo, Sing Sing is about the redemptive power of making art. “You do know that outside of these rooms, in the safe spaces that they created, there’s violence, there’s terror, there’s sort of hell on earth of the prison industrial complex,” says Domingo. “But inside this program, there’s grace, and tenderness, an opportunity to be gentle, and to use language, and art.”
They shot the film primarily in a prison that had only been decommissioned two weeks before they moved in. It was grim. “You knew how it all felt: how the air was stale, how you couldn’t find your true north, and what that does to you psychologically,” says Domingo. “Every time we had a break, I needed to go outside. While you’re in there, you’re like, ‘This doesn’t feel like a place for human beings, no matter what they’ve done or not done.’” People might reasonably expect the film to be gloomy. “But what I love is that there is so much light,” he says, “and joy, and hope. And it’s really funny.”
Kwedar says simply that he can’t believe how far they have come. When Sing Sing had its premiere in Toronto, A24 snapped it up the same week. After that… silence. A 2024 release was always planned, but Kwedar was worried that the magic dust would wear off, that it would just sit on a shelf forever. “And then we came back at SXSW, and it was almost more overwhelming.” There was even a screening in Sing Sing itself, in the theater space where Breaking the Mummy’s Curse was originally performed. They screened it in San Quentin. And now it’s in the Oscar race. “Anytime I pause and really think about what’s happening with this movie,” Kwedar says, “I just lose my breath.”
