Interview: ‘Sing Sing’ Director Greg Kwedar Talks About the Power of Colman Domingo and Protecting His Formerly Incarcerated Cast

There are not many films this year that have been as critically acclaimed as the Greg Kwedar-directed Sing Sing. The film premiered to rapturous acclaim at Toronto International Film Festival in 2023, finding a critical response that almost instantly declared the film as a front runner for the 97th Academy Awards and Colman Domingo as a favourite for Best Actor. In the run up to an inevitable For Your Consideration campaign, Sing Sing is now being slowly spread out to audiences across the world. A vast difference to Kwedar’s first film, Transpecos, which premiered in competition at South By Southwest in 2016 and took home the Audience Award before releasing on VOD a few months later. 

Kwedar’s sophomore feature Sing Sing, based on John H. Richardson’s Esquire article “The Sing Sing Follies,” premiered out of competition at the newly revitalised Edinburgh International Film Festival. The film follows the story of a theatre group that exists within the confines of New York prison Sing Sing. John ‘Divine G’ Whitfield (Colman Domingo) is a founding member of the Rehabilitation Through The Arts, a program designed to allow those incarcerated to channel the pain of their lives into theatre. The group usually perform the works of wrongfully imprisoned Divine G, whose cell has become a canvas for his literature, but the introduction of newest member Clarence Maclin (himself) disturbs the status quo. A power struggle occurs between Divine G and Clarence; the former seceding control of what the group perform, the latter in seceding to the groups rehabilitative power, while both take emotional chunks out of the other for healing. Instead of a Shakespearean drama like Divine G wants them to perform, they take Clarence’s idea of comedy and create ‘Breakin’ The Mummy’s Code,’ a sprawling time-traveling romp featuring (and not limited to) Hamlet, the wild wild west, Ancient Egypt and Freddy Kreuger and is directed for the stage by Brent Buelle (Paul Raci). The cast of Sing Sing is populated by the same formerly incarcerated men who partook in this original stage performance, with the exception of Mikey Mike (Sean San Jose).

I sat down with Greg Kwedar at the Edinburgh International Film Festival (EIFF24) to discuss Sing Sing, a film that works as an antithesis to decades of negative portrayals of those incarcerated in the American prison system. We chatted on how Colman Domingo and Clarence Maclin helped each other and both deserve their flowers, Super 16 film, his position as a white filmmaker taking on Black stories and his state of mind following an extended press tour that has months of For Your Consideration work still to go.

Connor Lightbody: It’s been nearly a year for you since the film just exploded at the TIFF Premiere. No one knew about it, now everyone knows about it. So I’d just like to check in. This is now the UK premiere, and the film has Oscar buzz so how are you doing mentally and figuratively, before that consideration campaign begins?  

Greg Kwedar: Wow, that’s a great question. I’ve done Q&A’s before, I’ve done press before. There was a familiarity to that. But what I wasn’t prepared for was the volume, the scale of it, you know? The reach of the conversations that I was having. I got a little freaked out from the level of exposure. You know, it was something far beyond what I’d ever encountered before. And you feel just a lack of control in a way, even though control is really an illusion. But with the conversations I was having, I at least knew and could see the reach it had, oftentimes in the same theater. You know, a lot of my early work didn’t travel as widely as this, and I got a little overwhelmed by the amount of information coming at you. The amount of reviews and interviews coming out. But the thing that honestly brought me back down to earth was that I remember flying home from that press tour, and I just closed my eyes and saw the faces of everyone that worked on the movie. It brought me immediately back to just this place of gratitude. Like it removed the pressure of all of this and there was an element of just letting go and being open about wherever this goes, wherever this travels. The movie now belongs to the world. What we have was each other, the process, all those faces, that’s what the experience was for us. 

CL: It has been quite a long press campaign so far and this hype and attention has felt at the moment very natural, which is good for a film that is as warm and empathetic as Sing Sing. It’s also very much a crowd pleaser, which I think comes from the film’s distinct lack of physical conflict. Was this a deliberate effort on your part to avoid prison tropes, specifically that of Black prisoners being violent?

GK: Without question. We felt like we were on this tightrope when making the film. Like if you fell on one side, you would fall back into the tropes and stereotypes that we were actively seeking to prevent. We wanted to present more dimension and complexity of the human beings that are incarcerated and the beauty still inherent within them that just needs to be reclaimed or rediscovered. And on the other side of that tightrope, it could be overly sentimental and feel conjured and not honest, you know? And so we were navigating that and not having debates about it because when you’re doing the work, you’re really just in the room with people trying to find something pure and it would be artificial to stop that. 

CL: Speaking of rooms, the film is liberatingly bright. Can we talk about achieving that and also the decision to shoot on Super 16 film?

GK: I mean, so much credit I have to give to the team of artists that brought the movie to life across all the crafts. Shooting on film came from our cinematographer Pat Scola, who came to it from a practical sense. Because we didn’t have the budget to sort of fully build out these worlds – the digital eye sees all, you know – and a lot of film is very forgiving. It can kind of fall away so we only really have to build out what we’re truly focusing on. But more importantly, the movie is really about the landscape of the human face. I think that the film medium is so loving for the textures of people and shooting on film allowed that to beautifully come to life. In acting, there’s a term for being in the moment, being present. Film forces you to do that because you don’t have the digital feedback to immediately go and check your work. You have to wait a full day for this film to be processed and scanned and it really does cause you to just be there for what’s happening and what’s unfolding.  

CL: I read that you once left the camera rolling after film had run out

GK: What you’re speaking about there were moments with our formerly incarcerated cast, where they were bringing forth something very deep from within themselves that they had actually lived. On film, there are times that you’ll literally run out of film. Normally on a set without the pressures of time and money and all that stuff, you would just say, “cut” (laughs) “new mag”, or, you know if it’s digital, you’d put in a new card. But what was happening there for that man was bigger than the movie we were making. And so there were times where, yeah, we would run outta film, but I wouldn’t call cut ’cause you know, that person needed the space to bring forth what was happening for them.

CL: Would you say the process for the actors was a form of therapy itself?  

GK: Isn’t it always? Why do we create art and why do we act? It’s a need for expression and connection to try to make sense out of a strange mystery of being alive? And I think it’s just more crystallised for this particular group of men who in many ways found their freedom behind these walls, through this work. They got to revisit those experiences and the community that they found that was so vibrant despite their environment.  

CL: You said they were revisiting experiences. What kind of precautions did you take in that regard to avoid re-triggering them in those scenarios?

GK: That is something we were very sensitive to, especially because of the locations we were shooting in. Particularly a max security prison that had been decommissioned a month before we went in, called Downstate. The entirety of our alumni cast had been incarcerated there at one point in their lives. So it was an active conversation. It wasn’t something that we were forcing upon the production but collectively with the men that were starring in the film. That being said, we still looked for traditional means of support. We had a therapist on set who had done work with these men when they were incarcerated at Sing Sing. But the surprising trigger that I wasn’t prepared for was when they were putting their greens back on again. Not even the setting that we were shooting within but them putting that uniform back on. You know, Divine Eye told me once that his body itched from putting that clothing back on. I think the power though was realizing that the purpose was greater than the discomfort. That transition of migrating from this being at one point in their lives a uniform that was mandated, to now being a consensual costume to express a character. And in that transition, there was a lot of empowerment that came through that clothing. Then the setting itself. Having freedom of movement in a place where you used to not have it was its own kind of purpose, a new opportunity to use a setting that was once something that was dehumanizing to something that’s very humanizing.

CL: There’s a real camaraderie with the cast. No doubt through the time they were formerly incarcerated together, but Paul [Raci], Colman [Domingo] and Sean [San Jose] were not. How did you help them slot into that dynamic?  

GK: It really starts at the top of the call sheet. I mean, Colman Domingo is an actor at the point in his career that he has full access to his powers. He could have come into this and use that as a form of leverage and control and to kind of take over. But he instead came in with a posture of being both a teacher and a student. There was a lot that he had to offer our alumni cast who had never acted in a film before, but recognized that he also had a lot to learn from these men about what it really felt like [in prison]. You can see that in the performance. It’s commanding but also generous to ensure that other people can shine. Then Paul really leaned on the real Brent Buell who was there every day on set. They were in this active dialogue and Paul had the humility to constantly go to Brent and ask him  “what would you have done in this situation?”, and “What would this feel like?” Then he would watch Brent actually interacting with the alumni that he had once taught so it was a very active and alive process. Sean had a very important role in providing a ballast for Colman because Coleman was coming into this experience that he had never done before of acting amongst all these people with lived experience. And Colman told me early on in prep that “I think I need a friend to come with me through this”. Sean is actually Colman’s real life best friend of over thirty years so he really provided a sense of comfort and security for Colman in this very unfamiliar form of working.  

CL: Colman is extraordinary and on track for a best actor nomination but I was most taken with Clarence Maclin  

GK: He’s a revelation.

CL: A complete revelation. What was the process in helping someone like him who was non-professional bring out such a strong performance in comparison to a consummate professional like Colman?

GK: I really hope they both get their flowers because I think the performances are what they unlocked in each other. It was the dance of it and the power bloomed collectively. They helped each other rise to new heights. Clarence was someone I met eight years ago at a breakfast at Brent’s apartment. When he walked through the door I felt that he was a star, you know, even then, all this time ago. He’s someone that has that special aura, the it factor thing. An indescribable magic, you know?

CL: Completely agree, he’s got this weirdly powerful gravitas to him

GK: Yeah he’s got charisma, but a real depth too. There’s a world-weariness to him, but it’s not a crutch; he still has light in him despite his trials. And all of that wrapped together is what makes him so special as a performer. He’s also someone who is just so observant about what’s happening and curious. He is constantly growing. The actor that he was on the first day of set had evolved into an entirely different one by the end. 

CL: Kind of reflects the character’s journey

GK: Yes, a very meta experience for us making this movie

CL: Dolly DeLeon is mentioned in the Special Thanks. Could you talk about what involvement she had in the process?  

GK: She is represented by one of my managers, Adam Kirsch, and happened to be in Austin, Texas on the press tour for Triangle of Sadness. They came to my house and watched the early cut of Sing Sing and she gave feedback on the movie. 

CL: In terms of the script: everything feels very easy and flowing throughout and authentic, as you said. Was there a kind of tangible script in place that people had to follow or was it a case of just letting them breathe and let them riff?

GK: Yeah, there was a script but the script really had three pillars. The story of the friendship between Divine Eye and Divine G was very scripted and developed through a unique process of writing and rehearsing at the same time with Colman and Divine Eye; then the production of Breaking the Mummy’s Code, which still had scripted elements throughout of things that were pertinent to the dramatic arc of the story but we tried to loosen our grip on it a bit and allow the chaos of putting on a show to come into the process and allow freedom for the actors to kind of find things in the moment while there was still structure; and then there were truly unscripted moments such as the Perfect Place exercise in the movie. Which was just a prompt from Brent, that then in turn the cast were answering that solely in their own voice and from their own stories.  

CL: The Sing Sing prison has a train running through it. How does that work logistically?

GK: The way it works is the Sing Sing complex is almost bisected by the train tracks, and the MTA North that comes from Manhattan and goes upstate actually goes through the complex. There are walls on either side and then walkways that are covered in razor wire over the tracks. So that’s what connects the two parts of the facility. It’s a constant reminder too, for the people inside, that they’re in one place and the rest of the world is in another, and continuing to move around them. So it is very unsettling for a lot of people who are inside. You can also just hear it through the walls and feel it throughout the place, several times an hour.

CL: There is a lot of discussion about who should be able to tell stories that aren’t necessarily their own. Could you go into why you chose to tell this story, especially as a white creative telling a Black story?

GK: Well, I gained my confidence to be involved in this project really through how the program itself functions inside. You know, prison is one of the most segregated places in the world, and yet despite that environment, the program was a place where you could put all of that aside and do something together. And within the process of making this film, I felt this was something that people from all different kinds of experiences could unify and tell a story about. Not just about what it means to be incarcerated but in its more concrete idea about what it means to find connection across our differences and tell a story about the joy that can be found in that despite the harshness of the world. The other thing I would say about your question is that I don’t personally subscribe to an auteur theory of filmmaking, where one filmmaker is the author of this whole story. This movie was made as a community in every sense of the word. I was one of many leaders of this project but in charge most specifically was the men who really lived it. They had the autonomy and the control over what was told about their own story.

Sing Sing had its UK premiere at Edinburgh International Film Festival and will be released in UK cinemas on August 30 by A24, in conjunction with We Are Parable. It is currently in select U.S. theatres.