Greg Kwedar’s Sing Sing is a truly rare gem – a deep and heartfelt examination of the healing power of art, performance, creativity, and friendship in truly tough circumstances. Based on the work of the Rehabilitation Through the Arts program inside Sing Sing, a maximum security prison in New York, it documents the production of a play staged, directed, and performed by the men who are incarcerated within its fenced walls. Though it is led by Oscar nominees Colman Domingo and Paul Raci, its cast is primarily made up of the men who, once, were a part of the program and saw it as a saving grace – a way to make friends, a way to express themselves, a way to escape.
It’s a truly sensitive, deeply felt, and emotionally resonant work, which is able to communicate so much about life within the prison system without falling upon tired cliches about doing time. After all, the men on screen lived through this: It is hard to default to a writer’s imagination when confronted with the reality of the justice system each day on set.
Vanyaland Film Editor Nick Johnston spoke to the director earlier this year, when Kwedar was in town to show his work at IFFBoston. The discussion is below.
Vanyaland: You started out as an accounting major at [Texas] A&M, right?
Greg Kwedar: Yes, I did. I’m an accounting major and an accounting dropout who left in the middle of the test in my senior year to become a filmmaker. And then, yeah. I really cut my teeth in documentary producing. But the thing I was always chasing was film. But that education I had in these other lives really shaped what my creative partner Clint [Bentley] and I have uncovered, which is this journalistic approach behind the curtain of worlds that oftentimes are ones you think you understand, but most people travel through the front door. But by going through the cellar door or the side window, we can present, hopefully, an entirely new understanding that was hiding in plain sight.
Yeah, absolutely. You’ve done a variety of different things in filmmaking, and I was wondering, how did your work in the documentary sphere affect this as a narrative film?
One of the things that we’ve started to discover with our first feature, Transpecos, was when someone is a subject in a documentary. They’re on camera for the most part; there are some rare exceptions, but for the most part, people immediately start to curate their story, self-edit, and try to present a version of themselves. But when we started to research these stories, we did not have cameras. We would preface that this was also going to be a work with fiction and that there was someplace for expansiveness and curiosity; people would say things to you off the record that were so much closer, to me, to the truth of, I think, what was happening in the story. And it just felt like a keyhole into these worlds that really fit my imagination. I’m also just someone who came up in a documentary, but I was really shaped and have a love of narrative. But I think that early training enabled doing the types of narratives where you let the world breathe into the films. And in that alchemy, something really magical happens for me personally, as an audience member.
That leads in well to the writing process, when you have a few people actively collaborating prior to shooting. I noticed there were, I think, four credited writers.
It’s based on a couple of sources, and then the story credit is shared between Clint and myself, but also the real Divine G and Clarence “Divine Eye” Maclin. And that wasn’t just a “Thanks for letting us tell your story” credit. It was integral to the process because, early on, we’ve worked on this for over eight years. Early on, Clint and I really tried to just do it ourselves. We would have all this research if we were volunteer teachers in the program. But then, we would go away, and we were like, “Let’s be writers now, and let’s channel all this and put it in our words and conjure it ourselves.” It always felt just like an imitation of what we had experienced as volunteers and in conversations with a lot of the alumni. It was always at arm’s length from what it felt like and was disappointing. And it was only once we opened that process that we brought the same community spirit that the program actually has to the storytelling, and it was like, “Ah, that’s what it was meant to be.”
Yeah. Given your experience with the program, I’m curious about the way you built trust, because you have your trust in your performers, and your performers should have to feel safe in a situation that’s emotionally charged like this. I imagine you have so many different pitfalls you could fall down. How did you go about establishing that trust with your cast?
Yeah. I don’t know that there was a specific conscious step-by-step path we traveled down. Trust can be something that you can earn fairly quickly if people feel your intentions align with theirs, if you sense, even in a first conversation, that there is a kinship and alignment of values. But however easy it is to gain it, if you lose it, it’s almost impossible to recover. So, really, it’s about staying consistent and really honoring the promises that you’ve made and protecting the space that you’ve built because it’s a very fragile veil from the cruelty of the world beyond that space and the sacredness of what’s inside of it. And if you threaten that, you may not ever be able to reclaim it.
I can imagine it must have been an experience for those guys to go back and shoot that. Were there moments in which you had to confront that?
Yeah. We, as a leadership team, were really nervous about what we were actually asking this cast to do, to come back inside a place downstate. Where we shot most of our interiors was a maximum security prison that had closed a month before we shot there. And all of our cast, at one point in their journey, had been incarcerated there, because most people begin their long bids in New York at this place. And so, Clarence has shared that the cell that we shot his scene in… I didn’t learn this until the Q&A circuit. He was actually incarcerated in a cell right above it when he was there.
Wow. That’s insane.
We took lots of precautions, and we were very open in dialogue, and we had a therapist on set, and it was all of that. But really, the therapy was the process. And this transformation of one of the most traumatizing things was actually putting greens back on, for many of men. A lot of our cast have never actually worn green in any part of their wardrobe since they’ve been home.
Jesus.
And so, going back and putting that on again… At first, Clarence also says that there was an itch, whether it was real or just in his mind, across his body when he put those on as if his body was almost rejecting them. But in his words, the importance of the work, the message, and what he wanted to put out there was worth more to him than the discomfort he had. And then, slowly, it becomes like, “Oh, this isn’t a mandate. This is not a uniform anymore. This is a costume and a means of creativity and expression, and I’m using this on my own terms now.”
It’s just so interesting, I think, when you see those interiors, and you see the spaces that you use. It must’ve been an interesting challenge to block some of those scenes. You’ve got a 10 to 12 person cast on screen at any time? Aside from the main auditorium, you have relatively cramped locations. How did you prevent that from ever getting out of hand or becoming too difficult to manage logistically?
Yeah. I was really nervous about that going into the project, “How will we achieve scope [in such a small location]?” And my first film, Transpecos, was set in a desert where I had 360 scope and openness. And now, we were behind walls, and razor wire, and tight corridors, and this labyrinth of what these prisons are designed to be. And then, conversations with our cinematographer, Pat Scola, really leaned on in the storytelling process, which is the realization of where we would find our scope in the landscape of a human face. And so, it was about drawing close to these people and the thousands of stories behind their eyes.
Exactly. I think that’s one of the things I really appreciated about it. I’ve always liked it when filmmakers get to shoot their shot in 70mm, and then they go out, and they make movies that are just all in medium close-up. You have such a rich emotional detail in the relationship between the camera and the subject and it all comes out, I think, in the performances. So in terms of just individual, say scene-to-scene, on-set, every day, all that stuff, how was the collaborative process between you and the cast? And then your other actors, who are incredibly talented but are holding court with hold court with Paul Raci, an Oscar nominee, and Colman, who was nominated for one last year?
I know. I think the confidence and the excitement came from the exchange of that. I think if we had just had two of our great actors, Colman and Paul, on screen, there would be an absence from this film that only the people with lived experience could have filled. And then, our established actors are able to [help bridge that gap]. Particularly, Colman is the eyes that we see this movie from. It is an extraordinary responsibility to be our guide through this multi-textured world and all of these people, stories, and faces. He really grounds the whole movie.
He does something that’s like how he is so commanding and yet generous, allowing everyone else to shine. That was a very hard needle hole to thread, as a performer, I think. And he really helped me distill this whole process of this ensemble down to three pillars, “To let it be honest, to be elegant, and to be tender.” That became a bit of a mantra for me, alongside the one within the film, which is, “Trust the process.” In their words, “It can be a shit show through the whole rehearsals, but then the magic can happen opening night if we focus on the work, and if we create the space, and if we take care of each other.”
Absolutely. When I walked out of my screening, I started to notice there were men there who had been struck emotionally by the film in a profound way. And I’d only seen that kind of visceral emotional reaction in a lobby after leaving two specific genres, and it’s always war films or prison films. I read your thesis quote on your site and what you make about people coming together in extraordinary circumstances.
Human connection in impossible places.
And I was thinking those genres are both defined by that. You’ve got, on one level, the battlefield, where you’re trapped and in immediate danger, and on another level, you’ve got a prison, where you’re trapped and in less immediate danger. It breeds a certain kind of connection between the people there. So, how do you honor that? How do you depict male friendship in a way that isn’t toxic? It’s a thing you engage within the film itself, where your characters are talking about, say, using “beloved” instead of more derogatory colloquial names for one another. So, how did you approach that?
Honestly, we just captured what was happening. We weren’t conjuring that. It was really there. It was there in between takes. It was there when we showed up in the morning, and that’s the community that was built. In a place like a maximum security prison, vulnerability is seen as a weakness. And so, all of these masks come on, and walls come up, and you hold on to that really tight.
But I think the program really became a space where you could actually put those aside, and you could start to see each other, and start to realize that that’s actually a position of strength. And then, once they started to perform for the entire population, to be celebrated for that… Because I think everyone out in that crowd is realizing like, “Oh, we’re also playing characters here.” The person inside also has the same needs to be seen, understood, and recognized. And so, that affirmation from the incarcerated audience to our cast on stage really, I think, enabled these men to hold onto that and carry it into their lives on the outside.
It reflects well in the way Divine G cameos in the film. That’s such a heartwarming moment in retrospect.
Yeah, once you have it put together, it’s really him asking for an autograph of his own book [from the person portraying him on screen]. There’s a lot of meta stuff in this movie.
I can imagine that. So, I’m curious: did you film the entire play?
[laughs] I’ve been asked this before. If you can recall the scene in the movie when he drops the scripts on their desk, it was a 147-page script.
[laughs] Absolutely.
That would’ve been impossible unless it was like a David Lean film or something. [laughs] No, but it was hard to figure out what was enough to both have in the spine of seeing that production unfold. You need these structural benchmarks: “What can we gather from when the play is first spitballed and where the idea took shape?” The ideas that were tossed around were wild and contradictory. You needed to see some expression of that later on paid off, particularly Freddy Krueger, and how Hamlet somehow is oddly wrapped up into this with the soliloquy.
But then what we really need to charge, we need to charge Divine Eye’s progression through that, and then him nailing it in rehearsals, and that being the fullness of the soliloquy. But then, to see the odd version of it on stage is maybe the thing to show at that point. And so, it was really about harnessing the visual dynamism of that production. That was one of the things I was first taken when I first discovered they actually did this. It was the collision of all of these tones, sets, and costumes, and you felt the childlike joy of it all. And I think I just wanted to translate that, at least give people a little taste. And then, maybe at some point, we’ll remount Mummy’s Code for the world.
I would love to see it.
[laughs] Yeah. So would Brent, I promise you.
On the one level, you’ve got the scenes within the compound, where people are just in their day-to-day lives, and then you’ve got the play itself. I imagine it must have been an interesting mix of emotions for your cast to go back and do those plays again. Was it a good…
To go back and do this particular production of Mummy’s Code, or?
Yeah, or just to see an echo of what they had done themselves back then.
Yeah. It’s like, “Wow, we were kids then.” But yet, I think not realizing how much they missed… Their incarceration, I don’t think anyone missed that, but they missed the magic of what this program was and the closeness of those friendships. Mummy’s Code, in particular, always held something in their collective memory. It stood apart. They had done a lot of classic plays, and all of them had a meaning to them, but this was this real bright spot in their time inside. And so, there was a fondness of the memory despite the circumstances they were in.
Yeah, totally. It’s an imaginative and wonderful little piece. It definitely is funny as hell, too. It’s right there. And you’ve got all that wonderful archival footage that you use at the end.
There is something really quite profound about that footage, about why it even exists, in that the reason those performances are actually taped is that they are sent home to their families.
Oh. I didn’t realize that.
And Dino, who’s so wonderful… In the movie, he’s the one who says, “We’re here to become human again.” He was one of the standout performers in his time inside and the star of many productions, and all those tapes went home. His son grew up watching those and actually just graduated from the Yale School of Drama.
Oh my God, that’s incredible.
Yeah.
Oh, man. And he is so good in it, too.
Yeah. He’s been doing a lot of work with at-risk teens, and that’s what he has made his career on the outside, as a community leader. But this has re-instilled his love of the screen and stage. He and Clarence Maclin both have representation as a result of this experience. And I think you’ll see a lot more from them soon.
Did they go to TIFF with you guys?
Yeah.
That must’ve been a crazy experience.
Yeah. For the audience, too, honestly, because this thing starts to happen as you watch the film. And if you get to experience it in a festival environment or a special event, at a certain point in the movie, you realize like, “Oh, wait. No one could have written that. Only someone could have lived it.” And then, you see that archival footage, and then you see that the majority of this cast is playing some version of themself. And then, to have that person walk from behind a curtain, on stage, in front of an audience, it is electric.
Man, that must have been a roar from that crowd.
I’ve seen this enough time… I mean, that was the first time, but I’ve seen it enough times now to know, “Yeah, everyone’s going to laugh at this moment, and this moment’s going to be like, ‘Ooh, ouch.'” But when it’s, the ripples between every little laughter and every emotional moment are palpable… That happened that night. I’ve heard anecdotally from a few people who have been going for 15 to 30 years that it was the longest-standing ovation that they had ever seen at a theater at TIFF.
I can imagine that. It’s well deserved.
Yeah. It was also an exchange between that audience who wanted to show their love and what was manifested inside themselves through watching it to that group of men. It was just this beautiful display of affection and energy. That was magic.
Yeah. It was even the same thing, just leaving my own little theater after the press screening. And I think that’s one of the things that I’ve really liked about telling friends about this is they-
Keep doing that. [laughs]
Trust me, I will. I put the word out to a group I’m in. They were like, “Oh, Oscar bait,” and then it faded away once they heard what it’s actually about. It’s like, “Oh, I got to go see this now.”
Yeah. Yeah. There’s a kind of earnestness to it of… It’s unapologetic about its emotion, and the spectrum of that, the joy of it, and the harder emotions to express and let go of. I think people… Because it wears its heart on its sleeve, I think… There’s a lot of work coming out that has, I think, a cynicism to it, and we’re feeling the darkness that surrounds us. And I’m personally growing more drawn to what I think of as a hard-won optimism. And not a naive one, but one that’s earned. And I think this movie travels that road.
Yeah. I genuinely, completely agree with you. And just as a final question, I guess, are you the kind of filmmaker that watches your movies in the theater? Because I would be way too shy.
I love it. I actually do. And I just realized how much of a privilege it is. I’m eight years between films that I directed, so I know that they don’t come around often. And I also know that with this movie, this opportunity might never come around again. It’s lightning in a bottle. And it makes me feel good to be with people in a dark room. I’ll leave you with this. This is a movie about the friendship of two people who came alive inside of a theater. I think that in these dark spaces, we watch these films, and the same opportunity exists for us as an audience. And so, whenever I can, I want to be there. I mean, now I at least have to watch the last 20 minutes. If I’m doing a Q&A, I need a vibe check for coming out.
This interview has been condensed and edited for clarity.