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Oscar-nominated Sing Sing filmmaking duo Greg Kwedar and Clint Bentley have been a partnership for as long as they’ve been making features. Back in 2016, their first film Transpecos, about border agents in the desert, cemented their like-minded connection, as they found they each approached narrative storytelling with the journalistic outlook of a documentarian.
Kwedar and Bentley regularly trade roles with each other, too. For Transpecos, Kwedar directed, then on their second feature, Jockey, Bentley took the helm. Kwedar directed Sing Sing, and now, for their next project, the Joel Edgerton-starrer Train Dreams, which recently debuted at Sundance, Bentley directs—such is the equal balance of their working relationship. And that true egalitarianism extends across their whole filmmaking process, through all the cast and crew, as they run equal-pay-and equity-for-all sets, an initiative they call Ethos. In conversation with Deadline, Bentley and Kwedar, who are Academy-nominated in Best Adapted Screenplay, with their lead, Colman Domingo, nominated in Best Actor, explain their hope for the future of independent film. And they unravel the beginnings of Sing Sing—the true story of men who find hope and community in writing and performing a play—and why making the film changed them both forever.
DEADLINE: Congratulations on the Oscar nominations. What was the spark that brought you together in the beginning?
CLINT BENTLEY: We’ve been working together now for I think coming up on 15 years. And we met both right after college. We graduated around the same time, but didn’t go to school together and neither of us went to film school either. My parents had moved to Texas when I was in college and I was visiting them. They were living out in the middle of nowhere and they met some people down in the same small town and I got to know their daughter. I had done some short documentary work, student film work, along the US-Mexico border and that was a big passion of mine.
Then this young woman, I was talking to her about all of that, and she said, “Oh, well you have to meet my friend Greg, who I went to school with.” He had a big passion around the US-Mexican border. And we hit it off fairly quickly. And we just started working together by being friends who wanted to be filmmakers, and supporting each other on our short films and things like that. Greg had an idea for a film called Transpecos that he wanted to write. He had a short film script and wanted to turn it into a feature. And we started collaborating on that. And then I ended up marrying that young woman who introduced us. So, it all worked out, really.
DEADLINE: I love how the story ends! Greg, maybe you can answer this one? What do you feel is the kernel of the thing that makes your working relationship functional and productive and creative?
KWEDAR: Clint got the easy one.
BENTLEY: Yeah, exactly. Greg gets the philosophical one, but you’re better at those anyways.
KWEDAR: I think our relationship is sort of foundational to how we began as filmmakers. We began together and we began trying to figure out how to tell a story about a world beyond what you could find in the news or reading a book. We were after some deeper understanding of a place and of people there. And so, our process was forged together. We were discovering how to be storytellers and how to become filmmakers in step with each other as we were becoming best friends at the same time. And making that first film took over six years, to the point where we actually shot it. And a large driver of that was we almost realized that we were trying to become journalists into these worlds first, and really peeling the curtain back and what we call building the story from the dirt up. Really coming into these worlds as people first, and listening, and befriending often the subjects of that world in a way that’s not transactional, but an exchange. And it just led to something that the essence of what we were seeking and then the next film… And I think the other thing that’s important to distinguish of a kernel that’s allowed for longevity is the fact that we write together and yet we’re both different directors. And when one of them as directs the other works in support often as a producer. And I think what that allows for is both a shared artistic journey that’s deeply meaningful because it’s shared. Being a filmmaker is often a very lonely enterprise, that you’re lonely in two ways. You’re lonely when it’s rough, and you’re here in the trenches, and you don’t think you can keep going and endure.
It’s also lonely at the rare peaks when you have something to celebrate, but you have no one to celebrate with. And so, to have that in place and yet, by being different directors, both still have that moment of being able to call the shots and actually follow your true instincts, but you have someone there who understands you and who you trust that can help support that vision coming to life. And I think what helps us be better directors is because we’ve had to work in support of someone else and be humbled by that too. And so much of our filmmaking, we’ve started to coin as community-driven filmmaking, of caring about the community we’re working within, as well as the community of our artists that surround us. We’ve seen the fruit of that, and the work that it takes to nurture that. And then that leads it into our projects, our sets, and the types of stories we tell.
DEADLINE: One of my major takeaways from Sing Sing was that we live in a time where I think there’s a lot of concern about where men are at in terms of mental health, and Sing Sing offers an answer with connection and community as it shows the men taking part in the Rehabilitation Through the Arts (RTA) program. Greg, you had heard about the RTA program while you were making a documentary, and then an Esquire magazine piece came out about the RTA. When did you see the story as a film?
KWEDAR: Thank you for what you’re saying about finding connection and the importance of that in male relationships. Tenderness was a key word throughout making Sing Sing that Colman [Domingo] helped us identify. But connection is actually kind of a cornerstone of Clint’s and my work. We actually wrote a mission statement down almost 15 years ago that we were going to tell stories of human connection in impossible places. It was kind of an instinct then, and it’s more of a committed practice now. It just has grown more urgent and vital to us the longer we’ve worked. And it’s something we always talk about, whenever we’re setting out on something. We honestly willingly go into some pretty dark places for our stories, but we’re looking for the light that is there.
DEADLINE: First you met the real guys behind the Sing Sing story. They had put on a play at Sing Sing and that became the foundation of the film, starring those formerly incarcerated men. What did you learn from that first meeting with the guys?
KWEDAR: Actually this past Monday night, an abridged version of that original play, Breaking the Mummy’s Code was performed at the New York Theater Workshop and I was there. It was with the original cast it was the first time it had been performed on a live stage in 20 years since the last time it was performed was when it happened at Sing Sing in 2005. With all the same actors.
DEADLINE: I can’t imagine how emotional that was for you, being there with those guys, after having made this huge film about them.
KWEDAR: It took me back to that feeling honestly, of first being exposed to the story. Which was, yes, when I learned about RTA, I knew it had the benchmarks of a story architecturally, of a story from casting to opening night. But it didn’t feel like something we had to do until I read about the production of this play, of Breaking the Mummy’s Code, this time-traveling musical comedy, which is just a totally bonkers play. But the genius within it, I think, is recapturing, playfulness, that first exposure you had to creativity as a kid, and the joy that you feel, which was something that had grown a little stale, or maybe I’d had my heart broken a little too much in this business.
But reading about that play and the way that the men felt putting it on in the environment that they were in, that was like a lightning bolt and just something that I felt like I needed to experience and that I’d lost something. So, my heart was sort of yearning to touch their joy, and I think that was the thing for me. And joy is an interesting thing because, and it’s clear that that’s the word, but it’s not happiness, which I think can be a fleeting thing. Joy sits deeper in the body and it’s something that can’t be shaken by your environment and it can’t be shaken by circumstance. It is something that belongs, that’s yours, and that no one can take from you. I don’t know what you thought, Clint?
BENTLEY: I remember when Greg first saw the young man with the rescue dog in the cell and thought about prison differently at that point and then found this article and sent me this article in the middle of the night. It was immediately clear there was a film there and that it would be an interesting film and feel different from the canon of prison films that is so tired and stale and really kind of destructive to the people and their families who’ve gone through this. Then the other thing is, we met a lot of resistance in getting this film off the ground from the industry side of things because Greg had made a film [Transpecos] that was a thriller, or had very much thriller bones to it, and they were just like, “No, more of that.”
Then we met the real Brent Buell [Sing Sing co-producer and the playwright who worked on the original Breaking the Mummy’s Code] and he set up this group of meetings for us in New York over a weekend. We met the real Divine Eye, we met Clarence [Maclin, who would star in the film], we met the real Divine G, John Whitfield [who would be played by Domingo]. We met Dino that weekend, we met Dap. A lot of the guys who ended up being in the film, we met that weekend. We met a lot of others who didn’t end up being in the film, but I just remember at the end of that weekend, we just spent a ton of time talking to them and to your point, we treated it like we were journalists: let’s discover just as much as we can and not go in with preconceived notions of, O.K. let’s find a plot, let’s find this. It was just like, let’s learn from these people what their lives are like, and what their thoughts and their hearts are like. I know I speak for both of us here, that our lives were changed after that weekend. Making a film at that point was important, but even if it had never happened, our lives were changed by being in concert with those people.
I think it’s a testament to what Greg has done as a director with this, it’s the same feeling that people have when they come out of this movie is that feeling that we had. And it’s by being in concert with these men who have been through this program and who have opened themselves up so miraculously… It’s almost revolutionary how much they open themselves up and how they’ve taken their masks off. And I distinctly remember that of just not only my world view was changed, but also, and I had different thoughts on what does it mean, a lot of the stereotypes that you develop just by being a person in America. No matter how liberal you are, a lot of the stereotypes that you have about what an “ex-convict” is or what that person is like, not only were those washed away, but then also just from a heart perspective, I wanted to be a better person because of being in concert with those guys.
DEADLINE: I’m curious about the resistance you got to the film—it’s not just because of the existing work that Greg had done directing, there’s also got to be this idea of, “How can we sell this perspective where there are no good or bad people? What do we do with that?”
BENTLEY: We were told it was not sellable. We were told this was not a good film to make or from a business sense.
KWEDAR: Or if you wanted to make it needed to conform to the stereotypes. And that was harder because you got the temptation of, well, we want to make it and what is the greater good? And maybe we can we did flirt with that, honestly. There were earlier drafts of scripts where we would try to weave in more some of the classic expected narratives into this thing that, but the movie didn’t want that and would always be pushing it out. And it felt false, it read false, it was not aligned with the experiences we had with the men we knew and as we became volunteer teachers ourselves in this program, we saw this firsthand. And we had a lot of accountability structure, the real Brent Buell, lDivine Eye and Divine G, who would read these things and hold us to a higher standard.
Again, we did this as a community and the community preserved the honesty that lies at the heart of the story. And I think it’s also important to point out that the stereotypes we have about incarcerated people are largely due to the movies we all grew up watching. So, our own industry has built this perception that we have about people inside. I think the power of a story like this is that it can expand that imagination, that there’s so much more that we can all be to each other. We’ve seen directly how that can work inside and outside the walls now that the movie is making its way into the world.
DEADLINE: I know that you opened up the writing process and shared it with the men whose story you were telling. I know that casting Coleman Domingo as Divine G was a dream come true. What was a peak experience for you both in the whole process?
BENTLEY: Just watching all of the guys from the program who, a lot of them in Sing Sing together at the same time, most of them had been in this play together and were now out and were now coming back together. And they had all kept in touch, but it was very rare that they had all gotten together like this. And so, there were a lot of days just seeing them hanging out, partying together, playing music together, catching up, just the overwhelming joy. It was a hard film to make. We were shooting it very quickly. But it was never hard emotionally, or it was never taxing. And a lot of that was because of just the joy that those guys were having together. And I remember on our last day, just feeling like if somehow the negatives got lost in the mail or the facility burned down and we lost all the negatives of this film, it was still worth it for everything that we’ve done with these guys and everything these guys have gone through. I just remember that overwhelming joy. It changed my view on not only what does it look like to make a film, but also just the value of art in our lives. It was so life-giving that it was all worth it.
KWEDAR: As Clint said, there were moments you’ll remember for the rest of your life that transcend the process that we normally go through when we make a movie. One example is we told the actors we were going to ask them some personal questions and that we wouldn’t reveal them until they were on set. So, they were prepared for that. But the questions would range from, why do you love acting? To, what roles have you played in other productions actions? Tell us a childhood story? What are you afraid of? Fight an imaginary gladiator… And Dino [Sean “Dino” Johnson, who stars as himself] had his audition and it got to the point where he was asked to tell a childhood story. It’s not in the film because it felt like to break up the story he told into a montage, it lost its power. But he tells the story of riding his bike and skidding behind the courthouse. And when he was doing it, a prison bus pulled up and he was like, Oh, that’s what the bad guys look like. But not a few years later, when he was 16 years old, he was on that same bus. And he looked out the windows and there were kids doing wheelies on their bikes. And he was like, I now realize what this one guy who I caught eyes with when I was a kid was trying to tell me, because he was looking at me like he was trying to tell me something. Basically, we have the ability to be our best and we have the ability to be our worst. And it’s something I think about to this day. Anyways, after he did this moment, the cameras stopped rolling, the set was kind of quiet and he just walked to a window and just stood there for a while. And then after a little while, Brent comes up beside him and just puts an arm around him. And then Mosi Eagle came up beside with him, put an arm around him. They just stood there by the window. And then he came back, and he fought an imaginary gladiator. And that’s what’s in the movie. These things that were just for these men and there were things that were just for our community, and it all is part of the fabric of what this became.
DEADLINE: Tell me about the decision to move forward with Ethos, your equal pay and equity initiative. You started it a while ago and it worked so well with Sing Sing.
BENTLEY: I think the film being done on this equity plan and equity model, that was very much we had done it with Jockey and seen the success of it, not only the success and the numbers, but the success of what it did for the crew and for the cast. And it just felt even more important to try and do that with this film, because of how it was structured and because of how many men were baring their souls. We had thoughts of maybe making a shingle of our own and trying to help other filmmakers do this same thing. And we did and still do want to, if we can ever get a second to catch our breath, we’re going to open source a lot of this information. We’ve been very open with it, just put some documentation out there that other people can just maybe download a packet.
Then there was such a call from the filmmaking community that there was such a desire to use this model from so many other filmmakers, and we had the desire to be able to help if possible. And so that’s just really where it came from, of wanting to, in one sense, get this out there as much as possible and empower as many other filmmakers to do it as who want to do it, and that’s really just where it came from. It seems like it’s not the only answer, but it’s maybe an answer that can make a little corner of our industry more healthy.
KWEDAR: It’s kind of similar with Sing Sing at its core, there’s a message of wherever people have access to art, they thrive. Again, it’s not rocket science that it works. That RTA has a recidivism rate of less than 3% against 60% nationwide. These are not groundbreaking ideas, it’s just what’s groundbreaking about it is actually following through and doing it. And I think what we’ve seen is, quantitatively and qualitatively, you can make movies at a lower risk, and by lowering the risk, the artists can be more bold in casting and creatively. And what’s I think surprising about it, and counterintuitive, is that through pay parity, it can be create a more level playing field for artists while also lowering risk and rewarding artists with equity.
Once you do that, there’s this mindset shift. This is where the qualitative happens, in the mindset shift of moving someone from an employee to a partner mindset. And just this idea that you’re going to take better care of something that belongs to you. You start to see artists thrive in the creativity and feel like when they’re a true stakeholder, the way ideas are offered, the level of work output and quality of work rises that makes the movie better. That then gives a chance for it to work out in the world and be profitable for everybody involved, which it has been for Sing Sing and Jockey. And to be able to write those checks, nothing feels better than that.