There’s more than one way to escape a prison. For the individuals incarcerated at Sing Sing Correctional Facility, Clint Eastwood’s spoon shovels are relics of a bygone era; enter Rehabilitation Through the Arts (RTA), a non-profit program offering another kind of escape hatch.
Since 1996, RTA participants at Sing Sing and beyond have staged theater productions ranging from Shakespearean classics to zany potpourri plays, extricating an artistic freedom independent of anything the merciless carceral system has taken from them. Deprived of their liberty, they have not – cannot – be deprived of their humanity, a fact RTA proves by providing a literal stage on which to be fully seen. Even in here, they can sing, and act, and dance. Even in here, they can be.
There’s also more than one way to make a prison movie. It’s not surprising that director Greg Kwedar and his co-writer/producer/creative partner, Clint Bentley, would take an empathetic approach to an often pitiless genre. After all, 2016’s Transpecos was a border-thriller defined by the grace notes of human decency that speckle such a harsh landscape, and 2021’s Jockey met the unforgiving sport of horse racing with unexpected forgiveness.
With Sing Sing, a new docu-fiction about RTA, they find their entry point into a traditionally tough world via the tenderness the program embodies. Together with like-minded producer Monique Walton (2019’s Bull, another story of unlikely connection), they worked with John “Divine G” Whitfield (a former RTA participant, novelist, and playwright portrayed by Colman Domingo in the film) and Clarence “Divine Eye” Maclin (another former RTA participant, who portrays himself in the film) to flesh out an inspiring story that dodges tropes by reflecting the true experiences of countless RTA alumni, many of whom join Maclin in playing themselves on screen.
If that sounds a little artsy, that’s the point. For people several barbed fences removed from all that they call home, art is a luxury they can afford, and there’s something especially moving about the way the men of Sing Sing embrace the vulnerability of theater in an environment seemingly designed to suffocate empathy. They hardly talk about the crimes they did or didn’t commit; instead, they volley the word “beloved” back and forth, leaning on their art (and each other) to build a collective bridge to the world they’re missing.
Far from stunt casting, the abundance of self-portraying RTA actors proves the program’s point; this is not a hope untethered from reality but drawn from it. That honesty means any happy ending is contextualized by the less happy ones that play out in Sing Sing and prisons everywhere, but the artists of RTA (and of Sing Sing) don’t let the existence of so much suffering preclude the persistence of beauty. To quote another ode to theater, it doesn’t matter if they don’t always understand the play – they “just keep telling the story.”
Ahead of the film’s release, I spoke to Kwedar, Bentley, and Walton about telling stories, hard-won optimism, and the necessity of art.
Despite being set almost entirely in prison, I feel like this movie is anything but a typical prison movie. I’m curious if you and the team, in prepping, turned to any classics of the “prison movie” genre, or if you looked elsewhere for inspiration?
Monique Walton (producer): I feel like that’s a great question for Clint and Greg.
Clint Bentley (co-writer): Yeah, it’s funny… the one we did talk about was not a prison movie. And I think more often it was about avoiding a lot of the tropes of prison movies. There’s a lot of stereotypes that are perpetuated throughout prison movies and prison shows. We wanted to do the opposite of that, and it was actually kind of difficult over the years of trying to get this made. When we were trying to find financing, we would go out with a script that did not have these prison tropes in it, and it would be rejected. And whatever development exec would be like, “Well, we just need a little bit more of, you know, violence,” or whatever… the thing that we’re so accustomed to seeing.
Mostly, I think, it would be in terms of just trying to do the opposite of those things, because we knew these people and we also taught inside of a prison as research for the movie and saw the exact opposite. The one [example] Greg would point to at times was feeling like it could be a cross between One Flew Over the Cuckoo’s Nest and a Michel Gondry film, and kind of finding how those two things can live together.
Greg Kwedar (director and co-writer): And things outside of the canon entirely, too. An early influence for me, right when I was starting in film, was Y Tu Mamá También. And I think the reason it knocked me out was like… movies can be made like that.
One thing I think that’s sort of imbued in a lot of our work is letting the world breathe into the film, creating space for the world to breathe into it. And I think that project, that’s why it stands apart in time and resonates even to this day. And I remember so clearly being in a theater and being so opened up by it and seeing so much possibility as an artist and feeling so much connection to it within my own taste.
It’s also a movie about the simplest things of just finding the perfect beach or getting laid. And yet it’s also about the deepest things at the same time, and the stuff of poetry. And that really has always stayed with me as we’ve grown as artists. So we were looking more into the well in that place, or like Kieślowski films. Short Term 12 was a more contemporary work that’s also kind of tapping an energy that feels appropriate to the work we’re doing.
Well, I mean, speaking of “outside the canon,” there’s a lot of Shakespeare in this movie: Midsummer Night’s Dream, King Lear, Hamlet. I’m curious if it was important that it wasn’t just theater speaking into the lives of these men, but specifically Shakespearean theater.
CB: So many of these things we were trying to just… not even translate, just be a vessel as storytellers for what they were doing inside. And that’s something that was echoed by a lot of the RTA members that we met, what an impact Shakespeare had on them.
Divine Eye says a version of it in the movie, but it comes from his real story, which was: he read some King Lear before he ever got into the program and had never been exposed to it, which says a lot about our education system in the country. But he’s sitting in prison, he’s reading King Lear, and not only was struck by the language, but then also felt like this was speaking specifically to his experience. And there’s something very wild and magical about that. Something that I think a lot of people think of as kind of stuffy is something that really was inspirational to him and a lot of the men in the program.
GK: Yeah. We were sensitive, though, not to kind of overwhelm the story with Shakespeare. Because that was something early on when I first discovered the program, which is now over eight years ago: in reading about it, I felt immediately the potential of the world and the architecture of a story, from casting to opening night behind the prison walls—that was all sort of right there in the beginning.
But if you were to dramatize this true life story, and the work that was being put on the stage was a drama or a tragedy or one of the classics—which they’ve done many of—inside such a dramatic place, it could yield melodrama as a movie. And so there’s something so potent and special about Breakin’ the Mummy’s Code, this time-traveling musical comedy, because of what it was speaking to in terms of tone… the playfulness of the work juxtaposed with the environment that it was set within.
Also, how it was this kind of madcap comedy with, like, dance numbers and rap numbers and a Hamlet soliloquy just thrown in there and the Black Plague and Roman gladiators and all this crazy shit. To us on the outside, as observers, the stakes might feel fairly low, putting on a show like this. But for the people inside doing it, it’s life or death to them. And we as visitors, as an audience, embrace the same sort of belief and beauty and passion that they feel for the work that they’re doing, and I think that’s something that we were drawn to as well. How do we recognize that the classics are alive in the world today and can have new meaning inside even Sing Sing, and yet at the same time, see the power of what originating something, and what throwing everything at the wall can still have?
Yeah, totally. I mean, I think that segues into what, to me, is one of the core themes of the film: this idea of art as a bridge between people, both in the sense that you’re talking about where these men are connecting to each other through the art that they share—be that Shakespeare, or breakdancing, or mummies—and then now, people are going to come see y’all’s movie and feel a new connection to these men and to men like them who’ve been incarcerated and beyond. What do you think it is about art writ large that gives it that connective power?
MW: What is it? I mean, I don’t know. Art is life.
I think one of the things that has become more defined in terms of making this film and talking about it and then seeing how people react to it is just this idea that art is necessary. It’s a necessary part of being human, the creation of art.
One of the mantras of RTA is “Trust the process,” which you hear in the film. And just this idea of approaching the film in that same way that RTA approached the process, where the goal was not to put on the most amazing play, the goal was the process of making the play, and what that brought out, and how that could bring out your humanity or help you deal with things in your life.
And so I think that in making the film, it created a way for us to really look at the process of making a film as like, let’s trust the process of making this film and create a collective experience for us that feels like the process itself is gonna benefit the artists that are actually creating it.
So I think that… I mean, art is just necessary. It’s just a necessary part of life. And I think it allows for space for us to kind of deal with things that are really hard to deal with without it.
So taking a step back: Monique, with Bull, and Greg and Clint, with Transpecos and Jockey and now Sing Sing – you all seem drawn to these stories of unexpected, even radical grace in some pretty hopeless places… or unexpected places, at least. And I think Sing Sing especially foregrounds that idea. What is it about these ideas of grace and mercy that seems to pull you all back? And how do you tell a hopeful story like this in what could be such a dark place?
GK: I mean, that’s a great question. Well it’s just funny, even the way you’re framing that is something we’re very conscious of now, and have been really from the beginning of our careers. When I came into the business—and you know a little bit of this, Justin—I was an accounting major dropout who was starting in film, and the first instinct was to write a business plan for my life or career, because that’s what business majors do. And the business plan was a bunch of nonsense, but the thing that has stuck with me, and now us, is the mission statement that I wrote down, which was to tell stories of human connection in impossible places. Which was like an instinct then, because I was just a baby filmmaker, and is now much more of a committed practice.
And I think it’s an evolving phrase, and you’re learning new layers with time and with every project, and I think at this point in my career, at least what it means to me—and maybe all of us can kind of answer in our own words on this—but I’m just interested in work that has a hard-won optimism. [Work] that’s not shy, and is actually very readily going into the spaces where connection with someone else might be most difficult, and the wounds are great, and there’s a lot of darkness, and it’s shitty. And yet, despite that, and in there, we can still find light.
And if you can come out of that hole and still have love and still believe… because what happens when you’re down in the depths of despair is it’s either going to crush you and you’re done and you’re just broken, there’s no coming back for it, or you climb out.
And if you climb out and you can still have love in you, I think it’s a more powerful kind, because we can all kind of recognize it in other people; we can see it and we trust it more than when it’s naive. The ones who have that earned optimism, it resonates for me.
What do y’all think?
MW: Yeah, what you said, Greg, it totally resonates with me too. And that’s something that we learned we shared as a worldview, this idea of these unlikely stories and connections happening in difficult places. But also just trying to reflect the world around us, taking this realist approach and trying to search for the honesty and the truth in the reflection of the people that we put on screen.
And in order to do that, it requires building relationships in a way that you don’t typically do. You actually do it more in documentary, I think, if you make documentary films in a certain way. But it’s not an approach that’s really taken in fiction because fiction filmmaking typically— especially an indie film where the resources are so limited—is all about efficiency and how to do something for the smallest amount of money possible.
But the work, and I think the work that Greg and Clint did on Sing Sing that really made itself into the fabric of the movie, the DNA of the movie, is the six years of development where it’s writing, and building relationships, and volunteering in prison, and meeting these guys where they are and understanding who they are.
And so I think that’s what really deeply compels me in my work, is how do you tell these stories in a way that feels honest and true, and involves the community in a way that feels mutually respectful, and a way that can really just enrich all of us.
CB: Yeah, these two have said it so well, there’s not much to add. We all share that desire, and I think that’s what’s connected us to all want to work together, that desire to show the world as it is, and take this neorealistic approach.
But then you spend so much time on a movie. You spend years of your life on it and you’re asking people to invest their time in it. And I think going back to something Monique was talking about earlier, to your question about “What is the point of art,” or “what do you hope that it can do?” – if art is just showing you how shitty the world is, that’s really probably not that helpful in this day and age, where every day we’re being bombarded, every time you open your phone you’re reminded of how shitty things are. But if you can show somebody, inspire them to step up out of that shittiness, showing that hard-won optimism or that hard-earned love, then that feels worth taking somebody’s time for.
Well, you kind of answered it there, Clint, but I was going to ask: I heard Colman say that if there were one thing that he hoped people could take away from the movie, it would be this idea that we’re more alike than unalike. So Greg or Monique, do you have an answer for the purest takeaway [from Sing Sing], if you could put it into people’s heads?
MW: It’s hard to answer for the audience because I think everyone brings their own reflection of themselves. I think for me, one of the things that I continue to sit with, with this film, is just how much our society and system is such that the people behind the walls of prison are supposed to be invisible. Like, it’s built for that. We ignore it. We don’t think about it very much.
And yet, we still, and still, have the most incarcerated population in the world. And so I think this is just another way to look at that, to really consider the human beings that are there. And I always think that any sort of change of mind or heart comes from imagining what a future could look like where this is not the case in this country.
GK: Yeah, beautiful.
[This interview has been edited and condensed for clarity.]