Colman Domingo has had meetings before. He’s had many of them. He’s met with filmmakers, writers, and producers. It’s part of the business. But there was something that sparked with a sit-down with director Clint Bentley and screenwriter Greg Kwedar. The filmmakers behind the acclaimed 2021 indie drama “Jockey” couldn’t nail adapting the true story of a rehabilitation for the arts program at Sing Sing Correctional Facility into a movie. They were looking for a true creative collaborator and, unlike some other projects, they were serious about wanting to actually partner with him on it.
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Domingo recalls them stating, ‘We would love to see how we can collaborate on this with you.’ I said, ‘In what way?’ ‘Well, for you to star in it and bring your writing skills and your directing skills and producing skills and really help shape this and be a part of it in practice.’ People may say that, but they follow through. ‘Oh, you really want all that because I’m all those things. I’m going to bring everything.’ And they weren’t afraid of it.”
Over many Zoom meetings, “Sing Sing,” which debuted at the 2023 Toronto International Film Festival, and arrives in theaters this month, began to take shape. Initially adapted from John Richardson‘s 2005 Esquire article “The Sing Sing Follies,” the movie centers on a veteran of the program, “Divine G” (Colman), who attempts to befriend a talented newcomer “Divine Eye” (Clarence Maclin), earn his release while they stage an original theatrical production for their fellow inmates. Machlin, who is essentially playing a character based on his own experience, for his perspective but when they finally had a working draft ready to shoot, reality set in. Domingo’s slate seemed full. He had already committed to a significant role in “The Color Purple” and the title role in “Rustin.” These were two major career opportunities that were essentially shooting back to back. But Bentley and Kwedar were undeterred.
“There was so much passion and urgency and I really took that in,” Domingo recalls. “And I thought, ‘O.K., lemme look at my schedule.’ And I think my team probably even thought I was crazy. I said, “Well, I have 18 days in between ‘The Color Purple’ and ‘Rustin.’ That’s all I have.’ They said, ‘We’ll take ’em.’ I said, ‘There’s no way we can do this movie, come on. But they were like, ‘We really can get it done.’ I sat with that and it just followed my gut on it. My instinct, I thought, ‘This has to be done.’”

An eventual Best Actor nominee for “Rustin,” Domingo used whatever time he had to help get the movie funded. Moreover, the production found a “beautiful” way to make sure was an equitable experience for the entire cast above and below the line. That was important to Domingo. And as the process continued, it was obvious the Emmy-Award winner appreciated just how genuine the partnership was.
“They asked me my opinion on everything,” Domingo says. “And I think we created something that has so much grace and love and smashing tropes and stereotypes that I feel very proud of. And I think that I know there’s a lot of my heart in it and it’s a lot of Reagan and Clint and also my comrades who went through the RTA program. Everyone feels ownership of this film. This is a film that we all wanted to make and we want to make and give whatever we had. No one left anything behind. Bring all of it, interrogate all the work at all times when we’re staging work, when we’re filming, in the edits, everything. Every step along the way. So, it feels closer to me than most projects.”
It almost goes without saying, but Domingo is almost in every scene in the movie. That meant very few free moments during filming. But he was ready for it.
“I didn’t feel the weight,” Domingo reveals. “I can look at my own work, which is why it’s probably difficult for me to watch. It’s more raw than I think I’ve ever been, but I was ready for it. I feel like as someone who’d been working for a long time, I was sort of ready for that challenge. I had to liberate myself in a way to actually do the work in a different way. So. that’s why I feel like it feels more raw. It feels more unmasked, but also that’s what I needed to do. My castmates, 95% of them are formerly incarcerated men who went through this program, and I didn’t want to stand out like a sore thumb. I wanted to fold myself in and be as raw and a little afraid around the edges as they are in performance.”
At its heart, the movie is centered on the real friendship Divine G shared with Divine Eye. Domingo notes, “The theater is what got them together. These people who you thought would never roll together suddenly depend on each other. And that’s that bond of brotherhood that was built. So, I got to know John just by getting to know him, knowing his heart, and knowing how he advocated for others, which I thought was very fascinating. Someone who was wrongly accused of a crime who was in prison for years, who still believed that the system could work. He took himself to the law library on a daily basis to try to advocate for his own freedom. So that told me everything I needed to know about the character and how to sort of distill him down into my body, someone who still has hope, someone who early on wanted to be a dancer but had to fight. When guys found out that he wanted to be a dancer, this dancer was still there.”
In a film full of powerful and moving moments – warning spoilers ahead – “Sing Sing” ends on a genuine cinematic tearjerker experience.
According to Domingo, one of the most challenging scenes was that ending. Domingo has to carry the weight of Divine G’s entire experience throughout the film and this is the pivotal moment when his life completely changes. He jokes that Kwedar will let you know he rewrote the ending “like 20 times.”
“I can’t sort of act it and know exactly what the scene has. I just have to be and take the experience of the film with me,” Domingo says of his process. “And I didn’t know that Clarence would have his arms open the moment I got up there and I think you even see me [react] like, ‘No, I can’t do that’ because it’s overwhelming what I’m carrying. He just lays that bear hug and the sound that comes out of me is guttural. And that’s all the information I distill about people being in institutions or wanting to get out of need. And it all just came out like a roar. And then that last car scene that was written, written, and rewritten. And by the time we got to that scene, Greg understood what he had and he said it exists in silence.”
“Sing Sing” opens in limited release on July 12