Examining both the dehumanizing experience of being in prison and the healing power of the creative arts, writer/director Greg Kwedar’s deeply moving drama Sing Sing is based on the real-life Rehabilitation Through the Arts (RTA) program at Sing Sing Maximum Security Prison (the program has branches in prisons throughout the country). The film centers on a group of incarcerated men who regularly put on theatrical shows for their fellow prisoners; the experience teaches them discipline, how to control and redirect emotions, and how to work with others toward a common, artistic goal.
The film stars veteran actors like Colman Domingo (Rustin) and Paul Raci (Sound of Metal), but most of the characters who surround them are men who were formerly incarcerated and are alumni of the program. Domingo plays John "Divine G" Whitfield, who had some exposure to theater writing and acting before going to jail, which makes him invaluable to the program. Raci plays Brent Buell, a non-inmate who effectively runs the group and gives acting classes. Throughout the course of the film, Divine G is also eager to find out if his parole will be granted.
Writing the screenplay with Clint Bentley, Kwedar explains in a recent conversation his first exposure to the story of these men who are incarcerated, and how he enlisted the help of producer Monique Walton to help cast the film with veterans of the program and the penal system, as well as how the film has become one of the year’s most celebrated since its debut at last year’s Toronto International Film Festival.
I’ll soon have another interview to share with some of the film’s cast members, but until then, please enjoy this conversation with Kwedar and Walton about getting this movie made. This interview was conducted just before their appearance at this year’s Chicago Critics Film Festival. Please enjoy…
When the original article in Esquire came out, obviously it’s a terrific story, but what about it said to you that it was a cinematic story. It really only takes place in a couple of locations, and we almost never leave the walls of the prison, so what about it said to you that you could make a movie out of it?
Greg Kwedar: When I first discovered the program, it felt cinematic to me in terms of exploring the prison system being wrapped up in stereotypes. Yet within this program, you have the architecture of casting to opening night, and it felt like the skeleton to explore something quite complex. All of the productions this program had done in the past were dramas, the classics like Shakespeare, On the Waterfront, A Few Good Men, and I had this fear that if you did the telling of a dramatic play inside such a dramatic world, it would feel like a melodrama. So the Esquire piece, detailing the putting on of this madcap time-traveling comedy, the wildness and wackiness of that play became a counterbalance to the darkness of the environment; it felt like that to me. It felt like it had a One Flew Over the Cuckoo’s Nest energy, but also a Michel Gondry film, like Be Kind, Rewind—a collision of those things. We didn’t necessarily know if it would be cinematic in the end; it just felt like a deep well and I would have more questions at the end of it than I began with, which is usually a good sign that it’s something worth exploring.
I don’t usually read press notes, but I consumed the press notes for this film to find out how much of this story and these characters were real, and I was surprised how much of it was based on reality. Monique, one of your earliest jobs on the film was calling up various alumni of this program and trying to get them in this movie. Tell me about how you explained it to them. Was there anyone who resisted? Or was it fairly easy to get people on board?
Monique Walton: It’s always interesting; that’s one of my favorite and least favorite parts of casting, especially when you’re casting people who haven’t worked on a film set before. You’re also trying to explain it in a way that makes sense, but also set expectations because it’s a small film. This film in particular had lots of different layers to it because it’s about a play that many of them were involved with, it’s about performing the play but it’s also behind the scenes, so you play yourself in the play but you also play yourself in real life. And there’s time travel in the play .
There really wasn’t much resistance. The one thing about the alumni is that they were all super open from the moment I picked up the phone and told them about it. They were just showing up with their full selves, and I had to match that and meet that. It really became figuring out if they could do it, if they were available, and on the creative side, we were trying to create the ensemble. Everyone was talented and bringing something unique to the film, so we had to figure out what our ensemble looked like.
It’s my understanding you first reached out to people who had been in this production.
GK: Right, but Dino , for example, wasn’t in this production, but he was such a legend of RTA, and there were so many exceptional performances that he’d done over the years. By and large, there was a lore to this particular production, and the ones who were in it had this fondness, despite what the play was, the experience making it stood apart. And the love that the cast had for Brent Buell, the volunteer teacher, was also a big determining factor. He wanted to be engaged and was a big part in helping us make this movie, and we really relied on him because he held tight and maintained these lifelong friendships after so many of them had gone home. Many of them lived with him in his house until they could get on their feet.
Since most of the actors didn’t have stage and screen experience, did you have to lean on Colman and Paul to show these guys the differences between the two types of acting?
GK: There was that, but I would say it was an exchange. Our established screen actors would be able to say “You have stage experience, but it’s all happening inside of this frame, and subtleties can come across in the way that a camera can pay close attention to what’s happening.” That was a learning process for most of our cast, and we leaned on our lead actors to help introduce them to that. One thing to say about Colman’s performance: to be as commanding as he is in this film, he’s also so generous. That’s a high-wire act that’s hard to pull off. And then our alumni cast, they’re bringing this tremendous life experience in these settings. “This is what it felt like, this is what it looked like. This is what is sounded and smelled like.” They’re helping shape that for the rest of our cast in ways that we would never have been able to introduce them to.
I know that you’d been working on this for seven or eight years. What was the thing that finally cracked the screenplay?
GK: The script went through three main iterations. One where we just tried to retell the article in many ways with this giant ensemble, and the movie didn’t really have anyone attached to it. Then we swung in the other direction, with a really tight point of view, a subjective experience film, but that lacked the spirit of community. So the final breakthrough was to tell the story of a friendship, and through this friendship, you could feel the power of community and introduce the family around them and tell a more complete story. Honestly, the breakthrough and why it took so long, was that Clint and I had these experiences with the alumni and conversations with volunteer teachers, and we’d go away and write our version of it.
We would try to conjure and invent it on a page, and it always fell short, it felt like an imitation of what we experienced when we were there, and the things that finally opened all this up was to step aside and let the community come into the storytelling process. Once we shifted into that approach, which is a very radical way for us to write that we’d never done before—literally in concert with Divine G and Divine Eye and also with Colman—it started to recapture that special energy that actually exists within the program.
You shot this there, in Sing Sing, right?
GK: Partially there. We had four locations.
Right, I remember seeing different locations in the credits. But they were all prisons. What were the disadvantages or challenges with that, and what were the advantages?
MW: We always knew that we wanted to film in real prisons. Part of it was that the space tells the story; you can't really re-create that, in terms of the authenticity that we were trying to show. Of course, initially we were looking to see if there were any prisons we could film in, and then we found a downstate correctional facility that had recently been decommissioned. We were the first production to film there, and it was the official intake prison for upstate New York, so all of the alumni cast had been to that prison.
Once we realized that was the place we wanted to film, we immediately started talking about how to create a safe environment for our cast. We didn’t know what was going to happen when we got in those doors. We talked about therapy and we found an actual therapist who had worked in Sing Sing with a lot of the alumni, and he came to set and talked to everyone. We told everyone that we had this therapist coming to set, but they didn’t end up using therapy in a traditional way. We found that the process of making the film itself had a therapeutic aspect to it. We also used a lot of the RTA principles in the making of the film, being in this exchange and being very open, giving space for catharsis to happen. So that was something that was a revelation that happened once we started.
GK: We were shooting this downstate in the summer, 10- to 12-hour days, it takes a toll, even on us as crew, but on everyone there. I can only imagine for our alumni cast, having to revisit these places, even though it was cathartic, it had an impact. I just can’t imagine the time that some of our men had to serve in a place like that, after we were there for a small stretch, after it was decommissioned, it was enough to give you nightmares. I had them for a while, really weird ones about being stuck in a cave. Humans aren’t meant to be caged like this.
MW: No one was upset when we moved out of that location, and we had to start there.
GK: That was the really special part of the production plan. We left the shoot in the theater space and the freedom of that. We would wrap at 3-4pm in the theater space, and we burned through those scenes because it was so welcoming and we were so excited to be there and have the world of the prison behind us.
I’ve seen the film twice now, and I noticed the second time how many different tones are going on. Some of it is funny, some is heavy, you have actors who have no film experience playing versions of themselves but the versions that don’t know how to act as well, especially Divine Eye, but you have these seasoned actors playing real people. There’s a lot going on. In the end, was the balance easy to strike or did you really have to work on that?
GK: It often felt like we were trying to hold it all together, just as Colman says in the one scene, “Dying is easy, comedy is hard.” The comedy came quite easily because the chemistry of the cast was happening between takes, so that was the spirit of that ensemble. Yes, we were accentuating that in the script, but the drama, particularly when Colman has his breakdown on stage, I remember being in the wings of that stage with tears rolling uncontrollably down my cheeks because of where he went to with this role. He brought so much to communicate those feelings.
What do you hope people leave the film thinking about?
MW: There is a lot to think about because the movie touches on a lot of things. On the one hand, it lets you sit with people who are incarcerated and you think about how many people are and how the number keeps going up every year. This country has the most incarcerated population. I think shifting your mindset to what the exposure to the arts did for these folks, having a life that is not punitive, it’s hard to do because we’ve created this stigma and we’ve disappeared these people from our society. I hope people would consider that. And just like we’ve gone through this catharsis and found a way to connect with each other, how might we imagine creating more opportunities for that?
GK: For me, someone said that our films tends to lean into issues that can be debated through a deeply human lens. Our movies have a message, you just can’t write it down. And I love that you didn’t ask what the message of the film is, because this is the kind of movie that’s making an emotional argument, and the strength of the argument is about drawing close to someone and looking them in the eyes and knowing someone’s story and seeing that they have a name and face and history. Through that exchange, they can’t be anything but human.
Both of you, thank you so much for being here and talking with me.
GK: Thanks for the great conversation.
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