Trust the Process: A Conversation with the Filmmakers Behind the Critically Acclaimed Film ‘Sing Sing’

Divine G (Colman Domingo), imprisoned at Sing Sing for a crime he didn’t commit, finds purpose by acting in a theatre group alongside other incarcerated men, including wary newcomer (Clarence Maclin), in this stirring true story of resilience, humanity, and the transformative power of art, starring an unforgettable ensemble cast of formerly incarcerated actors.

There are times when a film can give you a glimpse of hope about humanity, about the human condition that mostly goes unseen, and about real human connection with others. It can shape how you view the world and others. That's the deep impact films have - if you're lucky. And that comes wonderfully packaged in the beautifully poetic film Sing Sing. Living day-to-day behind those cement blocks and steel bars are humans – most convicted of unjust crimes or just at the wrong place at the wrong time – but human nonetheless. This film gives us an inside glimpse of what good can be done when we come together with compassion. 

Through the lens of director and co-writer Greg Kwedar, we witness a group of unlikely men coming together to play – seriously. They take the act of acting and diving into their imaginations in their whirlwind play that they conjure together quite seriously and with great earnestness. Underneath it all, a strong bond and vulnerable connection is developed and most importantly, lessons learned to carry them forward, if they choose. It’s all about trusting the process. 

And I'd be remiss not to mention a deeply profound performance by Colman Domingo as Jonathan 'Divine G' Whitfield (who recently won Outstanding Lead Performance from the Gotham Awards, and nominated for Best Actor by the Golden Globes), and Clarence Maclin along with the rest of the cast, who are also former prisoners and RTA alumni.

Greg Kwedar, along with Sing Sing co-writer Clint Bentley and producer Monique Walton, recently spoke with Script about their eight-year journey to making this film, based on the true story of former incarcerated people Clarence Maclin and Jonathan Whitfield, as well as the book written by their RTA play director Brent Buell. They also share insight into creating a safe space for the cast and crew, shooting in a real decommissioned prison, melding documentary and narrative storytelling techniques, and trusting the process as filmmakers. 

This interview has been edited for content and clarity.

Sadie Dean: When it came to finding this particular story – was it in the form of the book first, or an article that initially piqued your interest?

Greg Kwedar: We've been working on this at this point eight and a half years - so eight and a half years ago, I came across this story quite unexpectedly. I was producing a short documentary inside of a max security prison in Kansas and was my first time ever behind the walls of a prison. And on the tour of the facility, we were doing a film about something else, but I passed by a cell, and there was a young man raising a rescue dog inside of his cell, and it stopped me in my tracks, because it up ended all of the expectations I had about prison and incarcerated people that were built by the movies I grew up watching, our own industry - and here I was seeing healing that was happening in both directions between this man and this animal, and there was compassion in that room. So that night in the hotel room, I was just honestly, I was desperate to know was there anyone else out there doing things differently in prison?

And so, I typed that question into Google, ‘Who is doing things differently in prison?’ and near the top of the search field was this program in New York, Rehabilitation Through the Arts that was founded in 1996 at Sing Sing, and they had done all the classic plays and have been covered in a lot of the major press. But there was an Esquire magazine article that I read that night in Kansas all those years ago, about an original production of a time traveling musical comedy called Breakin’ The Mummy’s Code. [laughs] And I was just struck by the playfulness of the work, juxtaposing against the environment. The joy of the process was so apparent in those pages. And I was desperate to feel that in my own life.

I reached out to the real life, Brent Buell and RTA kind of in a flurry, and spoke to Brent very soon after, and had this wonderful conversation at the end of it, he was just like, 'If you really want to understand the story, you need to meet the men who lived it. Come to New York, come to my apartment, and we'll have breakfast.'

Clint Bentley: Greg sent me the article when he found it, and it was just as clear, like everything that he's saying, just came across as well. And thinking about Greg making that movie, it just seemed like a no-brainer and felt like something fresh to add to a genre that's full of a lot of tropes that are causing a lot of harm to the communities that they've made these films about.

Then over the next six years, it was a big process of learning, how do you translate everything that's special about it to a film? And so, we met the real Brent Buell. We met a lot of the guys who had been through the program, and now had come home. We met the real Divine Eye, Clarence Maclin, that first weekend, we met the real Divine G, John Whitfield. We met a lot of the people who ended up in the film, then six years later, when we shot it, we met on that first weekend. And that was really life changing, just getting to know them.

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And then over the course of that process, Greg and I became volunteers through RTA inside of a maximum security prison in New York, and it was really just a very long process of trying to figure out how to take that magic that they created and this joy that they had found in this awful place that they created for themselves, and how to translate that to a film. And we did draft after draft of the script that did not do that for a number of different reasons, we failed. And then it was only then years into the process, when we opened our writing process up to include Clarence and John Whitfield and Colman [Domingo], that it really coalesced into what it is now.

Sadie: There's something about this film that makes it feel like hybrid filmmaking, it could be a documentary, but there is that strong narrative structure and backbone. Monique, when you initially came on board as a producer, what resonated for you as an audience member, but also as a filmmaker? And then on top of all of that, being that anchor for your team and for this creative group, and creating that safe space for everyone involved, both behind the camera and the guys who are coming back to this place again and them sharing that vulnerability?

Monique Walton: I think you just touched on it - and I think one of the things that really stuck out to me when Greg and Clint first told me about this script, which was already six years into the process, [laughs] and they were like, 'Yeah, we're shooting this, no matter what in four months. Please join us.' [laughs] - was that vulnerability. And the first thing I thought when I heard it was this is about healing. This is about vulnerability. This is something that I haven't seen. And then, especially once I learned more about the play itself, and how silly it is and how playful it is, and how it's like you're really kind of threading a needle to tell this story in a way that captures that playfulness, but that also doesn't negate where they are and the environment that they're in, and the system that they're a part of.

And so, I thought that's a challenge as well, and I didn't fully know how it was going to work. And I always kind of look for things where it's like, I can see it, I can feel the core, and I can feel a world view, which is what I connect to, but I don't necessarily know exactly how it's going to happen, [laughs] and that's part of the fun of it. And so that was definitely a draw and compelling to me.

One of the first things when we thought about was, we're going to make this film very much grounded in authenticity. We're going to shoot in a real prison. One of the things we thought about was like, 'OK, how do we create that safe space for these men who are going back to this place of such trauma?' And had actually been at the decommissioned prison that we were filming in. 

The first thought was let's bring a therapist on board. So, I interviewed multiple therapists and talked to them about it, and we ended up finding a therapist who actually was familiar with a lot of the RTA alumni cast, because he had volunteered at Sing Sing before. And he said, 'We don't know what might happen, what might come up.' But he was able to come and join us on set, and we realized at that point that, in terms of like engaging with traditional therapy, that wasn't necessarily happening, but that there was kind of a built in safe space that we all kind of collectively created that was led by Greg in terms of creating the space where there was just kind of a looseness to the process and a way for everyone to feel empowered to engage in ways that they wouldn't normally do on a film set.

And then also, for the RTA alumni, they were kind of having a bit of a reunion and were able to be there for each other in the times that did get hard. But there were moments of catharsis that came up throughout that for many people. Clarence always talks about how he had an initial reaction about going back. Never thought he would go back into prison, but that he felt like the mission of telling this story was greater than those feelings. Like Mosi [Eagle], he got lost in the prison the very first day, it's like a maze, you're supposed to get lost. And we'd already had a talk about if things come up let's be there for each other. So, he already had that in his mind. And he said, ‘You know, I thought I was going to have a real visceral reaction, but then realized that I could open any door that I wanted. I could turn the lights on and off. I could move freely throughout the prison.’ And so, it became something else, and having that freedom was very cathartic for him. I think it was a collective effort, in the end, for all of us to figure out how to support each other.

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Sadie: For me as a viewer there seemed to be a very set thematic anchor. And it was something repeated constantly, “Trust the process.” And it’s greatly brought to light when their director Brent says “Men don’t get to be vulnerable with each other often.” Basically, trust the process. When it came to trusting the process of filmmaking and producing this film, and the joys of producing – the many unexpected fires, even if it’s a smooth production day - what was that like?

Monique: I learned to really trust the process on this movie. [laughs] That definitely became a mantra, that was something that came from RTA, and now it's like a mantra for my life. [laughs] Like every time there's anxiety or uncertainty, it's just like, ‘trust the process.’ And I think that because Greg and Clint both are very process-oriented and knew that the process was actually, which is kind of like what the film says as well, it's about the process. That's what's more important than the actual finished product.

And so, it's really embracing that, was something that I learned to do on this because it's true, you don't know. We're shooting on film. Most of our cast had never acted in a film, they've acted on stage, but not on film before. So, as a producer, you're already thinking about, 'OK, what is our budget coming in - we're going to blow up our budget on burning film, because we have to do many takes.' But I think that one of the things Greg did really well is just create that space, create that balance of the narrative structure and the narrative backbone of the film remaining intact, and the vision of the film remaining intact. But then also prioritizing the space for everyone to play and for these moments to happen that were improvisational, and again empowering people to say, ‘This is how we should do it,’ or to give their thoughts and really saying, 'This is what's going to make this film feel alive and feel real.'

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Greg: I think the process is where the life is. We say this often, it's important to question the process, not just kind of blindly inherit it, and make sure your process is reflective of the values of what you're seeking with the project, and as an artist and as a person, it's all woven together. And within that, it took us a long time to figure out how can fiction and documentary and stage and screen…we felt that they belonged in the movie and that the movie wouldn’t be what it is without the sum of all these parts, we just didn't know how it would all work together. That was the kind of risk in the swing of it. Would this be a hot mess or would the alchemy of all this transcend into something profound.

And even underneath that, the kind of humor and tragedy, sometimes happening within the same scene, would feel like it'd be dissonant and not work, but somehow also feels true to this world that we're operating within. There's all of these strange contrasts within this movie and within this environment. You have this sort of stunning natural landscape outside of these walls, but then you have these walls and this razor wire and all that. So, it's kind of everywhere you look, these things are kind of clashing together, but in the clash, there's kind of a strange poetry that emerges, and we just learned to kind of trust that and go with it.

And that was reflected in the script itself, in terms of where the ultimate sweet spot we found of having really traditional scripted scenes, which was largely between the friendship of Divine Eye and Divine G made it the spine the movie, and then the production of Mummy's Code, we would loosen our grip, and there'd still be scripted moments relevant to the overall story we were telling. But then in the actual making of the play, we would allow for more situational writing to emerge.

Clint: I think what Greg said about also questioning the process is an important thing, because we did that, not only within the script, where we kind of broke apart the way we had written scripts in the past, and the way scripts are traditionally written in trying to honor the people's stories that we were trying to be make the script a vessel for. And so, we would write a block of scenes and then present them to, on Zoom, to Colman and Clarence. And they would read these scenes cold, give us notes, give us feedback. We would go back and forth with them, and then we would go write a new block of scenes, and we would rewrite those. And so, it was a process of the script evolving as we were going along and doing something very different than anything we had done in a way that you can't see. You don't know if it's going to be a failure or not, but you have to trust that it's working on any individual part, and so you hope that that will add up to something bigger.

And then also in the way we structured the film itself of pay parity across everybody. We've spoken a lot about this, but just approaching the entire production in a very new way. We had done it on a smaller scale, but it wasn't something that anybody was used to in terms of paying everybody the same and sharing equity and really trying to make it a community-based project. And when you're doing something like that, you just have to trust that it's going to turn out OK, and to Greg's point, not be a total mess in the end. And anytime, I think for all of us, anytime we found ourselves letting go of that traditional control, it yielded something much better for any one of our units or departments that we would have been able to find without doing that.

Greg: I think a lot of it is fear driven on knowing, when a question gets asked, the director is supposed to know the answer, and if they don't, then that's a weakness. But I think we all collectively and really embraced that unknown and the power of saying 'I don't know' and then as a community, searching for whatever the answer was that day. And that's what yielded, I think, some of the beautiful surprises in the movie, that I think are some of my favorite elements of the movie.

Clint: It also yielded, in terms of talking about the writing, some of the best lines in the film come from the actors themselves, just riffing on something. Even what you just talked about of, of that Paul Raci as Brent saying something like, 'We don't get to be vulnerable often' that line was never in the script. That was just something that was happening. We created a space, and Greg created a space in the direction that things like that could come forth, that could clarify a scene or clarify the movie in itself. And that's some of the best-written stuff. And you can't as a writer take full credit for that, [laughs] you didn't write it. But something about that process yielded it, which is what you needed.

A24 is re-releasing Sing Sing in Theaters on January 17, 2024.