The first and best reason to see Sing Sing, the new feature from Transpecos director Greg Kwedar, is for the lead performance of Colman Domingo. One year after receiving an Academy Award nomination for his title role in Rustin, Domingo is even better as John “Divine G” Whitfield, a wrongfully incarcerated inmate of Sing Sing Correctional Facility. An accomplished author, Divine G was a member of Rehabilitation Through the Arts (RTA), a program founded at Sing Sing in 1996 that “helps people in prison develop critical life skills through the arts, modeling an approach to the justice system based on human dignity rather than punishment.” It was through this program that Divine G worked with volunteer theater director Brent Buell on various productions including (as recounted in a 2005 Esquire article, “The Sing Sing Follies,” by John H. Richardson) Breakin’ the Mummy’s Code, a sprawling, time-traveling, throw-everything-at-the-wall-and-see-what-sticks ensemble fantasy starring many incarcerated individuals in roles as diverse as Hamlet, Captain Hook and Freddy Krueger. It sort of makes sense when you see it.

Casting formerly incarcerated individuals to play many of the inmates, Kwedar’s Sing Sing premiered at last year’s Toronto International Film Festival and is now in limited theatrical release, expanding nationwide on August 2nd, courtesy of A24. I recently spoke to Kwedar about how he got involved in telling this story, shooting on Super 16 and screening the film at Sing Sing.

Filmmaker: I read that years ago you were working with a friend on a short documentary set in a maximum security prison in Wichita, Kansas and that that’s what would lead to you conducting additional research and coming across the Esquire article that would inspire Sing Sing. But while you were working on what would become this feature, your collaborator Clint Bentley’s feature Jockey got the go-ahead first, so you went off to produce that film and returned to the idea of Sing Sing years later. When did it actually become, in your eyes, a narrative feature worth pursuing? I know it’s a big question…

Kwedar: It’s a big question because it’s like, “OK, where in eight years should we focus?” [laughs]  But a lot of what [I envisioned the film] could be all happened in one night, that evening in Kansas in my hotel room where I discovered that there were [prison] programs out there doing things differently. I was literally typing into Google, “Who is doing things differently in prison?,” came across Rehabilitation Through the Arts and that opened up a world that was like a deep well where, if you traveled down to the bottom with your questions, you’d still have more questions once you arrived at the bottom. That’s a sign that something contains a lot of possibility, narratively.

It also provided a lot of clarity, as I immediately saw the architecture for a potential feature centered around the casting for the opening night of a production. All of the major press RTA had previously received was about [the organization] having put on all of the classic plays, most of them dramas, and if you were adapting a story about RTA and telling the story of them [putting on] a dramatic production of King Lear inside of a very dramatic place (i.e. Sing Sing), you might yield a melodrama. However, when I read the Esquire article, there was something about the tone of it, the playfulness of putting on this time-traveling musical comedy called Breakin’ the Mummy’s Code inside of this facility, [contrasted] with the reality that surrounds them, that just felt like real life to me. It felt like it could be our version of One Flew Over the Cuckoo’s Nest meets a Michel Gondry film, and [Gondry’s] Be Kind Rewind was a movie I immediately thought of at the time.

So, we had this feeling, we had this tone, we had the needle that we were trying to thread through the hole, but then each of the intervening years [of pre-production] were about how to properly render it. It was a struggle because our first crack at the script turned it into this giant ensemble with no clear lead [character]. We were just interested in everything and the reality was that you could make a movie about each of the men I’ve known over the years…and the script reflected that [laughs]. It was kind of a nightmare because it had no focus. We then course-corrected in the other direction by writing a script with a very tight, single point of view from almost a composite character of the many men that we met. So then [the script] was about one man’s journey through the program, from the outside in, but then that was too narrow because this is really a story about a community. I think it was eight months before we started production that we had to start from scratch again. The breakthrough I had was imagining that, “Oh, this is actually the story of a friendship” and through this friendship. These real men who we knew [Clarence “Divine Eye” Maclin and Divine G] are two guys who would not have been friends but for this circumstance and for this program, and it’s because of it that they became closer than family. We could then let the [incarcerated] community orbit around that friendship and present something that felt like what we had seen of the program with our own eyes.

Filmmaker: Was it by reaching out and volunteering with RTA and speaking with Brent Buell that you were first introduced to Divine Eye and Divine G?

Kwedar: The night that I read the Esquire piece, I wrote to the journalist John Richardson and wrote to Brent (Brent recalls that I did this in the middle of the night, but I don’t remember it exactly that way—maybe it was!) and was very earnest. I so clearly remember getting on the phone with him and him telling me, “If you want to know what’s really going on, you just need to meet the men themselves. Come to New York, I’ll set up a breakfast, and we’ll sit around the table and you should just listen.”

Divine Eye and Divine G walked through the door of that first breakfast, eight years ago, and I still remember it so clearly. When he first walked through the door, it was like you could almost feel Divine Eye before he entered the room… he really had that presence about him, that aura that [movie] stars have. And yet he has a way of speaking that allows him to distill very big feelings in this sort of poetic way in his own voice that draws you to him like moth to a light. When Divine G walked through the door, I remember his soulfulness, his passion for justice in all of its forms and his mind. He has such a curious mind and it left a mark [on me], even then. I can almost remember how it felt in the room.

Filmmaker: Even with all of your extensive preparation and research into this world, I’m curious if you ever still felt like you were an outsider into this world. Was there anything that you as a filmmaker were hesitant about, or needed to be reassured about to know that you were going to handle these stories with the dignity and respect they deserve? 

Kwedar: Those things became more apparent with time. We started with a lot of excitement that we were going to make this movie, but as the years wore on [in pre-production], we’d go up and down the creative rollercoaster and get turned around, become lost and grow frustrated, oftentimes by our own industry. We were chasing this thing that was very specific, of what happens inside these spaces, but often, whenever we would share the script of the story with more traditional Hollywood [types], they would want it to bend back towards the stereotypes our industry typically props up. It came to a point where I almost felt like maybe I don’t have what it takes to help shepherd this and should go back to making things that I [know how to] make or that are expected of me. For a long time, I’d been asking the question of “What should I do next?,” but it came to the point where I was like, “I need to ask a new question: If I could only make one more film, what would it be?” And it was always Sing Sing. Once I allowed myself to embrace that, a lot of things started to click into place. There became a lot of clarity, finally, in the story and the [idea of the] friendship [between two men] occurred the moment I asked myself that new question. And I opened a notebook and wrote the treatment for that new story in about 10 minutes and at the very bottom I wrote, “Colman Domingo as Divine G.” It literally happened like that.

Filmmaker: Colman has talked about how having 16 days in between two other film shoots is what ultimately freed him up to star in your movie. When that brief window of time opened in his schedule, was that the final push your team needed to move forward? The fact that you would have to work rapidly around his schedule?

Kwedar: I think that when a movie’s time is right and you acknowledge and embrace it, the universe starts to conspire to help you make it. I wrote Colman’s name down in the notebook and made that intention known. My manager, Adam, happened to know Colman’s agent, so the two got in touch, shared the Esquire article between them (since we were starting [the script] over again, we didn’t actually have a script to share at the time), then we all got on Zoom together. Colman was like, “I read the article and have so many questions” and I was like, “Well, I want to tell you about the six years that happened from when we first discovered this article,” and then told him the story of this new version of the narrative we had thought up. Colman responded, “At this point in my career, I’m realizing that there are some projects that are trying to teach you something. You don’t know what it is but you just know that it’s trying to, and, at this point in my life, I’m saying ‘yes’ to those projects…and I’ve got three weeks open in July.” I responded, “We’ll take them.” 

A big reason why I had that confidence, honestly, is because of how Clint and I have evolved in our process of making independent films. We started on Jockey and were scaling it into Sing Sing, this community-based approach to financial structure and pay parity, which allows us to make our films at a much more approachable budget while making things more transparent and fair for the artists. [In addition to everyone who works on the film being paid the same rate, sweat equity shares—over 80 accumulated on Sing Sing—are paid out once the film’s distribution rights are sold]. And so on that Zoom (Clint was on there as well), I told Colman, “We can make this movie one of two ways: there’s the normal way where we pay you a bunch of money and need a studio for [financing], but I don’t know when we’re going to be able to make that film, if ever. Then there’s this other way that we experimented with on our last film that could really make for a beautiful process on this project in particular, one dealing with so many people who have been taken advantage of by [various] systems and are comprised of formerly incarcerated actors.” Colman responded, “Well, that sounds beautiful, let’s do it that way.” 

We had no idea where we were going to shoot the film. I mean, we didn’t have a script and didn’t have financing, but we recognized that it was time for the movie to happen and that there were people who wanted to be a part of this train that was leaving the station. Once you have real dates on a calendar that you can mark out, it creates an authentic sense of urgency that makes things move. We knew we wanted to work in real locations, as you can’t make a movie called Sing Sing without demonstrating what’s so significant about the place, how iconic it is. Its name has become almost synonymous with prison, and yet by telling this story, we’re trying to redefine its name for ourselves. It was important to show it in all of its specificity: its walls set against the Hudson River, the [Hudson] line on the Metro-North Railroad that travels through the yard several times an hour. But because we were a narrative production, not a documentary, we needed to have our own space [for the majority of the shoot], so we shot at Downstate Correctional Facility [a maximum-security prison decommissioned in 2022 after 43 years in operation], which we used [for] the interiors and stitched them together in the edit, along with a couple of other locations [such as Beacon High School] that we used for our scenes [in the] theater space. 

When you walk onto a location, if it taps into something almost primal and inspires ideas and speaks to you, I believe those feelings will also convey to each of the filmmaking departments and speak to them too. That’s why we sought out these locations—they’re priceless in their value. However, one of the things we had to think very intently about with this particular film was that we were working inside a facility, at Downstate, where our entire alumni cast had been incarcerated at one point in their lives. Could that potentially be re-traumatizing? How could we sensitively approach that? It was a bit of a “trust the process” approach, and as much as we could prepare, we did. We brought on a therapist to have on set who had worked with a lot of the men back when they were serving time, but the main healing experience involved in the making of this film was really how, despite the discomfort of putting the greens [uniforms] back on and going into this facility that many had been incarcerated in, this could be turned into an act of liberation in and of itself. How could putting these greens back on be about [putting on] a costume? How could this prison we were shooting in be looked upon as a set and as a place for creative expression? That was a beautiful transformation for all of us.

Filmmaker: Were you shooting on 35mm or on 16mm?

Kwedar: Super 16.

Filmmaker: While I know the film takes place in 2005, in part due to the that being the year the Esquire article was published, to me the film also feels of an even earlier time period. Maybe that’s due to the film grain, the softness of the image, or even the dirt specks that pop up throughout. Why the choice to shoot on film? 

Kwedar: All the credit goes to our cinematographer, Pat Scola, who really fought for that. As soon as we started talking about the story, he was like, “It just has to be on film”—and look, I know that’s something a lot of cinematographers will say, but he could back it up. For a movie that’s about the landscape of a human face, [shooting on] film really brings out the textures on people, and that became immediately clear as soon as we tested the medium. So much of the movie is about the process of finally bearing yourself, so film—being a truly physical, organic medium—contributed in a way that I probably can’t even put into words. You can just feel it. Clint and I have always wanted our films to feel like they’re equally of the world now while feeling like they’re existing outside of time. Prison itself contributes to that sensation too. Time is weird there.

Filmmaker: And most of these physical spaces were built in a vastly different era.

Kwedar: I mean, the term “the big house” originally came from Sing Sing and to “go up the river” meant you were traveling up the Hudson to prison. There’s all of this history—these ghosts, in many ways—within those walls. The way time passes when you’re incarcerated is also something I think film helps contribute to [showing]. They talk a lot about “slow time” and “fast time” in prison. “Slow time” is your feeling like you’re melting through a day very slowly. “Fast time” is the time you experience that you wish you could slow down, where you’re almost soaring beyond the walls and through your imagination, through an artistic process. [For these men], that usually happened when they were performing on a stage. That’s the only form of time I think a lot of these men wish they could slow down.

Filmmaker: When you first take us into the men’s makeshift rehearsal room, a large space filled with brick and chipped wood, the camera approaches the space from a low angle and on a track, slowly pushing in thru a narrow doorway and into this larger room with high ceilings where the next scene will take place. There’s a noticeable yet subtle glide your camera is doing in that moment and I wanted to ask what went into the planning of that shot.

Kwedar: I think that particular shot accomplished two things. One is that Pat and I were trying to recreate how it felt when we first scouted that location, how it felt when we first walked into that room and how cavernous, yet warm and inviting, it felt and how it took our breath away. I also think what that shot is saying, particularly being on tracks, is “Hey, pay attention here. This is where something is going to happen, this is the room where something really beautiful is going to unfold.” I think that the visual language helps convey that. I got excited about collaborating with Pat because he never believed in adhering strictly to one language throughout the film. We let the script and the storytelling tell us what a scene needed. There were clearer delineations elsewhere [in the film] where, whenever we’re in the more formal prison setting, especially early in the film, the photography is also very formal, blocked off, and trying to replicate the stillness involved in the way someone moves through the prison. It’s very confining, you don’t have autonomy, and every movement is mandated by someone else. We then took those feelings and let them blossom into the theater space where you have a sort of freedom of movement, where the camera, in turn, is acting responsive to that and is starting to dance alongside these characters. 

Filmmaker: I know you recently screened the film at Sing Sing for a group of incarcerated individuals. What was that experience like? 

Kwedar: First off, one thing that was important to all of us, but particularly important for our alumni cast, was that we can’t overlook one of the most essential audiences for this movie, which is incarcerated people. Our alumni had come to a [shared] vision of wanting to screen this movie in prisons all across America and, concurrently, to be in the room for each of those moments, to be able to be on a stage with an audience and start the discussion about what access to programs like RTA could look like and how we can work to expand the idea of what’s possible. So, if this was a big, hairy goal that we all wanted to hold onto as a team, we had to first bring the film to where it all started, which was inside Sing Sing.

For several weeks leading up to the event, I felt like I was preparing for what my emotional state would be like to go back inside. While I’ve gone to Sing Sing several times, I’d never actually been in the chapel, a room I had spent years trying to articulate on a page as a screenwriter but had never actually felt in my bones. Walking into that room [for the screening], I felt my body almost shaking a bit and was losing a grip on being able to control my feelings. This all came [to a head] when I introduced the film and was looking out into this audience of incarcerated men, most of whom were current members of the [RTA] program. I actually locked eyes with someone who was one of my former students when I was a volunteer teacher at a [different] facility and who was now [at Sing Sing]. I walked out of that room, broke down into tears, composed myself, went back in and sat down for the screening. Different things hit harder when you’re with men who are living through it right now. I’ll try to say this in a way without any spoilers but what freedom feels like and what it feels like to have the wind on your face again and to be outside of these prison walls is something you could feel everyone in the room yearning for. That was both beautiful and really hard to sit through, especially after it was all done. Half of the audience were civilians and half of the audience were incarcerated who were then told to stand up, individually counted and taken back to their cells.

Filmmaker: There was a hopeful aspect to the screening but also their current reality is…

Kwedar: Sobering, yeah.