Colman Domingo stars in Sing Sing, based on the real-life accomplishments of the “Rehabilitation Through the Arts” program at New York’s Sing Sing prison. How successful is the RTA program? Successful enough that many of the main cast are portrayed by formerly incarcerated actors, alumni of the program who are portraying versions of themselves.

The film follows The Color Purple star as John “Divine G” Whitfield, who comes into conflict with Clarence “Divine Eye” Maclin (playing himself), a hardened soul who nevertheless takes a chance and signs up to participate in the RTA program. Divine Eye must learn to shed his toxic masculinity and remove his emotional armor, while Divine G has to wrestle with his ego and this unorthodox new player, all while both men struggle under the state-sanctioned dehumanization of America’s infamous prison system.

While promoting the theatrical release of Sing Sing, co-writer and director Greg Kwedar sat down for an interview with Screen Rant. He talks about his introduction to the RTA program and how it inspired him to create the film, and how its themes of friendship and perseverance are universal to the human experience. He also talks about the film’s unique casting and how having real formerly incarcerated actors helped elevate the film beyond any “prison movie” that’s ever been made.

Director Greg Kwedar On The Transformative Power Of Rehabilitation Through The Arts

Screen Rant: The movie is incredible. I’m so glad I got to see it it’s one of a kind.

Greg Kwedar: Thank you.

First of all, did you have any involvement in Rehab Through the Arts? And what made you go, this has got to be a movie.

Greg Kwedar: It’s kind of wild. You know, I discovered the story over eight years ago. I was producing a short documentary inside of a maximum security prison in Kansas, and it was my first time ever behind the walls. And we were doing a doc about something else. But on a tour of the facility, I passed by a cell and there was a young man raising a rescue dog inside of a cell. And immediately, my expectations about prison and people in prison was upended because I saw the healing that was happening in both directions between this young man and this animal. And I was just desperate to know more about who was doing things differently in prison.

That began an eight year journey that ultimately led me to become a volunteer in the program with my creative partner, Clint. We taught an acting class. I’ve seen firsthand the power of this work and what happens in these rooms and how beautiful the energy is of all these people who are desperate for connection and to put down the masks and to really do this work and to allow their creative spirits to soar. We walked away from that experience feeling like, if we could just capture the energy of what it felt like, we’d have a movie. It just was really hard to figure out how to do that.

At the end of the day, the way we ultimately figured out how to do it was by inviting the alumni into this creative process, first with Divine Eye and Divine G, and then Colman and then the rest of the alumni that are in our movie. And by doing the work in a community way, like it actually happens, like, adapting that into the filmmaking process, it unlocked the energy. You couldn’t do it traditionally and capture that spirit.

It feels authentic in a way that so many prison movies don’t. They call them detention centers or rehabilitation centers, but the only rehabilitation that happens is when the people who are incarcerated do it themselves with programs like this. It’s so tragic and fascinating.

Greg Kwedar: It’s the power of these programs, theater being one example, a rescue dog program, like I witnessed all those years ago being another. It’s all about these doorways that start to open a possibility. Once you start, your spirit sort of comes alive and shows you not just where you are, but who you can be. A prison environment is designed to create a culture where you can’t possibly be yourself. You have to put up so many walls just to protect yourself. And this type of work is about sort of peeling those away. And what you might find there is actually maybe the most beautiful part about yourself, the thing that you were trying to protect for so long.

Sing Sing’s Authenticity Extends To Its Shooting Locations

And you shot in real prisons, too, right?

Greg Kwedar: We shot for a day at the real Sing Sing. So all the exteriors are the real place. It’s such an iconic setting. And there’s the juxtaposition between all of those walls and razor wire and then the Hudson River and the mountains beyond it. It’s also one of the only prisons in the world where a commuter train goes through the yard, literally through the yard several times an hour.

But the majority of our actual interior prison work was at a place called Downstate, which had closed a month before we went in there. We were the first sort of outside production to ever be in this place. And it was a facility that if you were going to serve a long bid in New York State, you would start at Downstate and then matriculate to other facilities across the state. So our entire alumni cast had been incarcerated there at one point in their life, which was something we were very sensitive about and aware od. And it was hard for our cast.

But what I’ve heard time and again from our alumni is that, whatever discomfort we were feeling, the purpose was greater, you know, of getting to tell our own story. And the transformation that starts to happen when, you know, the realization that these greens they’re wearing are just a costume to convey a character and not a mandate. And so there’s something liberating in that transition that happens through the process of making the film.

Sure. Yeah, it’s very well said. I think I grew up in Fishkill. I used to take the Metro North up and down when I was a kid. But you always are aware that, just a couple of stops down is Ossining, kind of an unassuming little place, where Sing Sing is.

Greg Kwedar: Oh, wow. Okay. And Downstate is actually in Fishkill, where we shot. It’s a little more hidden away. it’s kind of hard to miss Sing Sing, but Downstate is a rough place, tucked away in the hills there.

The movie is already winning awards, and everyone’s raving about Domingo Colman, as they should be. Tell me a little bit about that journey of now finally being able to share with everyone what you’ve been doing. How do you feel about the press that the movie’s been getting?

Greg Kwedar: Yeah, I mean, it’s very surreal when you start to realize that this thing that you’ve dedicated so much of your life to with some really wonderful people is now, it’s now bigger than us, you know. And also in a certain way, it doesn’t really belong to us anymore. We’re in this transitionary state where we’re handing off the movie that was so special to us. The process of making it is where our memories are, of the making of it.

Now, we’re in this liminal state where we’re handing the movie to the audience and we get to be a part of that exchange and doing these Q&As and these premieres and all that, It’s a joy to watch an audience start to feel the love and care that we had in making it. That they’re expressing it back to us is one of the beautiful things about the theatrical experience and being in this dark room together and having all of our feels.

I was thinking about the themes of the movie and how Clarence’s character had to make the choice to audition, even if he immediately regrets it. At the same time, so many people in prison are only there because they got unlucky, because they’re the ones that the cops tackled, or they happened to look enough like someone else. Is that something that you were conscious of while making the movie, just that idea of chance and choice?

Greg Kwedar: No, but I love the beautiful surprise of how artistic work is interpreted and that’s part of the exchange that we have, of you as a writer, having seen this film and it’s channeling on a wavelength that sometimes we’re not even conscious of as the artists making it.

I think what you’re raising is this idea of “leaning in,” and Clarence was someone who got respect for a long time through fear and yet had all this capacity for love that just no one ever asked of him until Divine G entered his orbit. And there was already something that the program itself was already creating this magnetic pull towards Clarence because it stood for something and it had values. And if you were ever in the audience for one of these shows, you felt the beauty of that process and that beauty is an invitation.

I think great things happen when people like Divine G stand for something, and then for others who hear that and overcome that nervous anxiety wanting to step in, but feeling afraid of what it might unlock. I think we just need to take that first step and someone else will take a step towards you.

It’s just that idea of letting that wall down, or even just removing a single brick so you can peek through is so powerful in the movie. I was talking to people afterward, asking, “When did you cry?” And the answers were all different, but they were all tears of joy.

Greg Kwedar: You know, the testimony of this film to friendship, you know, in all of its forms, you know, with Mike-Mike’s story being about the beauty of an old friend, of a lasting friendship and that shorthand you have. Sean San José plays Mike-Mike in the film and he’s Coleman’s real life oldest best friend. I mean, they’ve been friends for over 30 years and that comes across on screen, you know? And then there’s the beauty of the new friends, the ones that kind of come into your life and just sort of shake everything up and, you know, kind of move you into motion, you know, in terms of your own journey and in the shifting way that they can support each other.

I don’t know that I would have fully understood the value of that if I didn’t have my real life best friend as a creative partner, Clint Bentley. I mean, we’ve been doing this for so long that when one of us is down, the other one is up and extends their hand. It makes the peaks of moments like this worth it because you have someone to help through the tough times. And then, you know, the cameras turn off and people start stop asking questions and you’re back to the grind again. And everyone forgets who you are, except for that friend who still sees you and still believes in you. And that’s how we’ve been able to keep going all this time. I wouldn’t have been able to do it without him.

You and Clint are making the movie with these guys who have lived this unique experience. Did anything foundational change because of the input of these guys, your actors?

Greg Kwedar: Without question. Really, at every level. Even in the script phase, because I can’t really say that we wrote that, you know? We did bring everything we have to that material and really contributed a lot of significant work to it. But we told it in concert with the real Divine Eye and Divine G. I mean, they have a ‘story by’ credit, and that’s not just like a ‘thank you.’ That was really because of their active participation and telling their own story, as well as Colman, too.

He’s not just an actor, but he’s a playwright and a director and a screenwriter. And he brought so much amazing insight into the storytelling process, the dramaturgy as well as experiences from his own life. I mean, the script really became this vessel for us to put all of ourselves into it. And then we were able to sort of help curate that and harness it as writers. But it wouldn’t be what it is without the community effort. There are several sequences in the film that are just situations, you know, where we created a moment where a question was posed of the men of the room, and then we just turn the camera on. And these men spoke from the depths of their souls. I mean, no one could have written that. You could only have lived it.

When you’ve got these actors of varying experience and life experience and, you know, behind the camera or in front of the camera experience, does it does it all just kind of go away once the ball starts rolling? What’s that process like?

Greg Kwedar: It’s very alive.I mean, it’s electric, honestly, because you are you’re integrating, you know, a tremendous amount of craft with actors like Colman and Paul Raci and Sean San José with a room full of men who are actually from this program, who are real alumni, and they have a tremendous amount of craft from the stage. But many were acting in their first feature film. And so that kind of vulnerability and discovery was so attractive to be around. It kind of reminded all of us on set who have maybe been a little hardened by by the industry of just how beautiful a gift it is to be able to make movies. They brought so much. Every department had something to learn from these men.

About Sing Sing

A theater troupe finds escape from the realities of incarceration through the creativity of putting on a play in this film based on a real-life rehabilitation program and featuring a cast that includes formerly incarcerated actors.

Check out our other Sing Sing interviews here:

• Colman Domingo & Clarence “Divine Eye” Maclin
• Jon-Adrian “JJ” Velasquez & Sean “Dino” Johnson
• Cast & Crew at SXSW