Awards Insider Exclusive

Inside Sing Sing, the Colman Domingo Prison Drama That Will Break Your Heart

Domingo may be headed back to the Oscars for his incandescent performance in A24’s innovative film, in which he stars opposite several formerly incarcerated men.
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Courtesy of A24.

Colman Domingo had three weeks. He was about to go into production on The Color Purple musical film, with pickup shoots for the biopic Rustin scheduled for shortly thereafter. But in the small break between those projects, the actor was theoretically available. He said as much to writer-director Greg Kwedar over Zoom, in their first conversation about Sing Sing.

There was no script yet. No financing. Still, those three weeks looked good to Kwedar. “I was like, ‘I’ll take them,’” the director says with a laugh. “‘I guarantee you we can be ready to shoot.’” Domingo recalls being taken aback—and impressed: “It was crazy, but I liked that spirit. I like people who are on the edge that way.” That leap of faith has resulted in one of the year’s best, most innovative, and surprising films.

In 2016, Kwedar and his longtime cowriter Clint Bentley were introduced to Sing Sing Correctional Facility’s Rehabilitation Through the Arts program, which immerses incarcerated people into the worlds of theater, dance, and more. The pair shadowed RTA’s leadership, taught workshops, and got to know some of the program’s alumni. They saw how it quite literally saved lives. Sing Sing is the product not just of that extensive research period, but also the direct testimony of people who were formerly incarcerated and rediscovered themselves through the program. Marking Kwedar’s first directorial effort since his feature debut Transpecos (2016), it’s a startling, raw piece of work.

Yet the timing of Sing Sing’s world premiere at last year’s Toronto International Film Festival seemed potentially unfortunate. Fewer eyeballs than usual were on the event due to the SAG-AFTRA strike, which prevented most talent from attending. Sing Sing was also an especially unknown entity as it sought US distribution. But the independent movie had secured an interim agreement from the actors’ union, meaning Domingo, an executive producer who also plays the lead role, could attend the fest (despite not being able to support his other movie there, Netflix’s Rustin, which would go on to net him his first Oscar nomination). Some supporting cast joined him—no small feat, since 13 of the Sing Sing actors are RTA alumni, and anyone convicted of a felony is not typically permitted to travel to Canada. After six months of work with top immigration attorneys, five actors were ultimately cleared to fly just two days before the screening.

How did it go? Well, nine or so months later, I’m sitting with Domingo and Kwedar in Los Angeles’ London Hotel, where Sing Sing is screening for Academy members and press. The movie was a smash in Toronto, swiftly acquired by A24, and is slated for a July 12 release. It’s been playing all over the country at regional festivals since, meeting teary standing ovations from coast to coast; the awards buzz is already deafening. But perhaps more importantly, audiences are discovering and falling hard for the film. “We have a long, long road ahead,” Domingo tells me. “But I love the way the seeds are being planted for this. It feels very organic and very thoughtful—it’s not just a big blast. It’s letting it be something for the people.”

Kwedar agrees: “It mirrors our process of how we made it.”

The big idea for Sing Sing was to recapture the big feelings of the RTA program: the energy, the heartbreak, the triumph. But every time the filmmakers started outlining a screenplay, it felt all wrong—an “imitation,” Kwedar says, of what they witnessed in those spaces. Then they landed on the real-life story of two RTA members who formed a profound bond: John “Divine G” Whitfield, a dancer and aspiring actor who says he was convicted of a homicide he did not commit, and Clarence “Divine Eye” Maclin, once among Sing Sing’s most feared individuals. They met in RTA and supported each other through some of their darkest moments. Their bond would be the heart of the film.

“I wrote a treatment out in about 10 minutes of that story, and at the very bottom of that treatment, I wrote, ‘Colman Domingo as Divine G,’” Kwedar says. “I just manifested that shit.”

Domingo wound up being one of only a handful of professional screen actors to appear in the movie, a short list that also includes Oscar nominee Paul Raci, who plays the program’s director Brent Buell, and Domingo’s close friend Sean San José, who portrays Divine G’s roommate in prison. “I realized that if I’m one of the rare film actors in it, I’ve got to continue to find a place to be generous and help my partners,” Domingo says. “But also, they’re going to help me do something different. Land me in a different space of performance that maybe I haven’t been in ever before.”

He’s not kidding. Domingo has certainly showcased his transformative abilities in projects like Rustin, The Color Purple, and Zola—but here, he is utterly, emotionally naked. You can feel the ensemble keeping him on his toes too. “How hard to both command every scene but to be generous at the same time and to lift everyone up around you—I marvel at it every time I see the film,” Kwedar says softly, turning to Domingo between sips of his old-fashioned. “There’s so much of you that exudes through this performance—you’re someone who rightfully takes up space, but knows everyone in the room, and looks everyone in the eyes and listens.”

Kwedar’s visual approach centers his actors, appropriate for a movie about the power of theater and acting. “[Cinematographer] Pat Scola was like, ‘Oh, this is a movie about the landscape of the human face,’” Kwedar says. “What happens when you look someone in the eyes, in an unflinching way? What stories does the face tell?” Domingo has nowhere to hide in this movie, and makes every moment count. The same goes for his costar, Divine Eye himself.

Kwedar with Domingo.

Courtesy of A24.

Clarence Maclin was a self-professed “yard bandit” in Sing Sing until one day, when the prison yard was shut down, he wandered into Chapel and saw some peers putting on a play. It took him a minute to realize that the same people he was seeing every day were on that stage, disappearing into new worlds. “I said, ‘Oh, I’ve got to get up on stage—I’ve got to be a part of this,’” he tells me. “Then I had to stay out of trouble for a whole year in order to qualify, to get into the program, and it was a difficult task for me—because at the time I was getting into a lot of trouble.” He managed, going on to play Oedipus in Oedipus Rex, sing in West Side Story, and chew on August Wilson’s dialogue in Jitney.

“I was unloading my own baggage through these stories,” he says. “I was dissecting whatever I was going through.” Now formerly incarcerated, Maclin works as a consultant and ambassador for RTA—and may have a bright future onscreen ahead of him, if his rather astounding debut in Sing Sing is any indication. In the movie’s opening act, Kwedar holds patient, painterly shots on Maclin simply sitting and taking the world in, as if to tell the audience: Pay attention to this guy and this performance.

Maclin and Whitfield joined the writing process early on, since they were intimately involved in the basis for its script: the mounting of RTA’s original play Breakin’ the Mummy’s Code, a time-traveling musical comedy that also includes a Hamlet monologue. Kwedar and Bentley would write out a scene, then they’d get on a Zoom with their two subjects. They’d share their screen, the script would pop up, and Maclin and Whitfield would react. “They would read it cold, talk about it—what was resonating, what was off, but also where could it go from there.” Maclin says his main contribution was ensuring authenticity in dialogue: “They don’t really know the prison language, how we carry and conduct ourselves every day,” he says before chuckling to himself. “There’s certain things we would never say, like, ‘Gee whiz! Golly!’ We would never say that.”

Maclin and Whitfield received a “Story by” credit on the screenplay, and are also executive producers. Along with the rest of the cast and crew, they participated in a novel parity-pay model that Kwedar and Bentley piloted on their previous film, Jockey, wherein everyone (including Domingo) is paid the same rate and gets an equity share.

For Maclin and others, there was apprehension about getting involved in Sing Sing at all. While they trusted Kwedar, signing on would mean filming at Downstate Correctional Facility, an intake prison that at one point held all of the RTA alums in Sing Sing. “One of the scenes that I shot in there, I was right downstairs from a cell that I was actually in when I was in this prison,” Maclin says. Filming the movie could be painful, but just in signing on, he understood its necessity. “I’m a lot more than just an ex-offender, a prisoner, and we need the world to see that,” he says. “A lot of men behind these walls [are] a lot more than that three-second mistake that they made, that took their life away and brought them here.”

Clint Bentley, Kwedar, Domingo, Monique Walton, and Clarence Maclin at the Sing Sing world premiere in Toronto.

Jemal Countess/Getty Images

Kwedar tells me and Domingo that he’s going to duck out of our interview a bit early to watch the end of Sing Sing with the audience. The climactic scene, a startling moment of connection between Divine G and Divine Eye, ends with Domingo in an almost primal state, making a noise so guttural he can’t even recall where it came from. “I wasn’t aware of it, what that sound was—it was uncontrolled,” he says. He’s not quite ready to watch it again.

Before he leaves, Kwedar reveals to Domingo a secret about the making of that scene. Before filming began, Domingo pulled the director aside and said, “This is too much.” He asked Kwedar to promise that he’d tell Maclin not to touch his scene partner, to give Domingo his space. Kwedar promised. “I’m sorry but not sorry,” Kwedar says now. “I then went over to Divine Eye and I said, ‘Colman is in the middle of something right now, and he’s asked me to promise him not to touch him—and all I’ll ask of you is that, whatever happens, do not let him go. Pull him close.’” He believed Domingo and Maclin’s bond was strong enough to give the actor what he actually needed—closeness. Domingo smiles and appears on the verge of tears as he takes the news in: “That was the right thing,” he says.

One could also view it as the culmination of the “signpost” that Domingo gave Kwedar, way back in that first Zoom: to make the film “tender.” This is the most radical thing about Sing Sing. Its depiction of men who are incarcerated elicits tears not because Kwedar traffics in prison-drama clichés, but because each character and performance is approached with an open heart. “To watch men of color—mostly hetero—be tender is an act of revolution,” Domingo says. “I think that that’s what these men are reaching for, to redefine themselves in the world…. There are so many stigmas and tropes and ideas about men of color, and I want to help do my part in debunking that, and show that we hurt and we feel frail.”

Maclin started out in Sing Sing with a reputation for violence and manipulation. Same goes for the Divine Eye we meet in the film. We get to know him and watch him change deeply from there, which feels like a revelation. That’s what Maclin hopes, anyway. “If we never take the time to invest in others, we’ll never see the beauty they possess on the inside,” he says. “That’s where the world misses out.”


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