"If I could only make one more film, what would it be?”

A conversation with Greg Kwedar, the writer/director of SING SING.

---

Sipping a soda water inside a local Austin coffee spot, filmmaker Greg Kwedar is a creative with a big heart. Alongside his creative partner, Clint Bentley, Greg has produced three narrative features, all centering around real people in real, misunderstood places.

From his exploration of the U.S. Border Patrol to his deep dive into horse jockeys, Greg is committed to listening and learning from a community long before he puts his pen to the metaphorical page. With his new film, SING SING, Greg and Clint explore a group of incarcerated men who create a theatre community inside a max-security prison.

As a gal with a theatre degree, this film touched me to my core. SING SING is seven plus years in the making, and it's involved countless hours of research, collaboration, writing, and rewriting. Greg and I met up at Austin Film Festival 2023, and we talked all about his creative process, including his incurable curiosity and commitment to telling stories. 

​Here is a snippet from our conversation, and I hope it inspires you to get up and create!

--
Career Beginnings:
PR: When did you first realize that you wanted to be a filmmaker and what dreams did you have that you hoped to accomplish?
 
GK: Well, I was an accounting major in college... I was a rugby player and I was overseas in Australia in Sydney. It was the first time that I had just pure quiet to start to listen to my own inner voice… and I just kept remembering this teacher in my junior of high school in my AP English class [who] was just like, “You have a really interesting voice, you should try writing!” I dismissed it back in high school, and six-plus years later, it was coming back. It was just playing in my head again.
 
I started to write in a journal and just was writing little short film script ideas... I found there was a film school in Sydney pretty nearby to where I was living at the time, [and] I went on a tour of the school. At the end of the tour, we were in the basement of the building, and these two women were casting their student short film and just handed me the audition sides and were like, “Hey, can you read these?”... After we were done with the auditions, they were like, “What are you doing in two weeks? You want to be a PA on this short?” And I was like, “I don't know what that is, but sure.”
 
I showed up on the set, and it was just like this curtain got pulled back, and I just witnessed with my own eyes, like, the greatest artistic collaboration on Earth is happening in real-time in front of me. I came home to school, and in the middle of my first accounting test my senior year, I dropped out to be a filmmaker.
 
PR: Wow. I'm picturing a huge dramatic moment. What did it look like? Did you go tell your teacher?
 
GK: It was a big lecture hall. We were all on Scantron, and I was halfway through the exam… and all of a sudden, I started hearing… it sounded like everyone was using their pencils on the Scantron almost in unison. The sound just got louder and louder in my head… Before I realized it, I was halfway to the front of the lecture hall with my test, and I just handed it in halfway finished and walked out.
 
PR: That's a short film right there in itself!
 
GK: But to your question on what dreams still persisted… right at the beginning, because I came from a business background, I wrote a business plan for my career as a filmmaker. A lot of it is nonsense, but the mission statement that I wrote down is still applicable almost fifteen years later... I wanted to tell stories of human connection in impossible places. And that is something that I continue to find new dimensions of, continues to inspire me, continues to challenge me, and it continues to be a North star for me.
 
Choosing Stories to Tell:
PR: All of your projects seem to have this real-world connection... I was wondering what draws you to telling these real-world stories, versus, I don't know, magic or something?
 
GK: Yeah. I don't know. I'm curious if I ever try [magic], you know. But, for me, I'm really drawn to worlds that most people think they understand. Any other storyteller maybe would go through the front door, but we come in through the cellar door or the side window and present an entirely new understanding of this world that was hiding in plain sight... I come from a documentary background, and so does my creative partner, and we like to say is we are journalists first and then narrative storytellers. We're telling a story with [a community]; we never want it to be a transactional experience, but [for it] to be an exchange. And so, our process is oftentimes going into a community that's interesting to us and building it from the dirt up, really learning and listening first… Sometimes, it can take a very, very long time to arrive at the story we want to tell.
 
PR: What do you see as the two sides to the exchange? What do you receive and what do the other people receive?
 
GK: Well, we receive the gift of whatever the special knowledge is that that community possesses, and whatever they have to teach us about what it means to be human. Whatever expertise, you know, that might be tied to that community… whether it's horse racing… or the theater process… [or] the deeper poetry of their purpose... And I think that what we offer is to elevate their story so that the rest of the world can look in and find common understanding and inspiration.
 
Balancing Creativity and Career:
PR: How do you balance having what seems like a full-time job of interviewing and volunteering while also maintaining your life? 
 
GK: I am still trying to figure that out. But it's through having a number of projects at any given time… After my first movie, Transpecos… I sort of started to get involved more in the industry, [and] I was really listening to the voice in my head of like, "What should I do next?" I got to a point where I hadn't directed a film in seven years. And I was in this kind of like crisis of meaning and I was like, "Oh, I'm unhappy! I have been listening to this voice from myself and from everyone around me of what I should do next. I need to ask a new question…"
 
And the new question was, "If I could only make one more film, what would it be?” As soon as I did that... It was crystal clear, it was SING SING. It finally was the light switch going off that put everything else in motion to finally make that film... But, we're trying to find ways that we can maintain a process like this but still sustain ourselves and have, you know, flourishing professional lives.
 
SING SING: Development Process:
PR: What kind of research was involved in the process of developing a project like [SING SING], and how long did it take?
 
GK: We worked on [SING SING] for over 7.5 years. The origin story is that I was producing a short documentary in a maximum-security prison in Wichita, Kansas. It was my first time ever going inside a prison, and on the tour of the facility… There was a young man raising a rescue dog inside of a cell. Immediately in this passing image, I saw the tenderness that was happening in that room, and I saw the healing that was happening in both directions... The dog provides a path to healing to a young man, and the man provides healing to this animal. It just completely upended all my expectations of prison and prisoners largely built up in our own industry. The film industry has perpetuated a lot of stereotypes through the canon of films.
 
I was in the hotel room that night, and I was desperate to know more about who was doing things differently in prison, [so I] just typed it into Google. And at the top of the search field was this program in New York: “Rehabilitation through the Arts”. They had been putting on plays inside of SING SING for over fifteen years at the time, and they've been covered in the New York Times, The New Yorker and NPR, and they've done all the classics... But there was an Esquire article about one of the only original productions they'd ever done, which is a time-traveling musical comedy called Breaking the Mummy's Code… There was something so fascinating about this bonkers, wacky play inside of such a dramatic world that it felt like this unique tone, you know?
 
Because if we were to do a film about the production of Hamlet, which is inherently such a drama inside of a very dramatic setting, I think it could yield a melodrama as a movie. But this weird play inside of this dramatic world could be like our One Flew Over the Cuckoo's Nest meets a Michel Gondry film. And I was really captivated by the possibility of that.
 
And so [Clint and I's] first thing that we did was we made a bunch of outreach. [We reached out] to the journalist who wrote the article, the theater teacher who wrote this play, and RTA and just started building some initial interest around the idea of us potentially collaborating on a movie together… Brent, the theater teacher, was organizing these breakfasts in New York where we would just have coffee and start hearing stories from a lot of the people who were in the movie... We met at those coffees.
 
The next step in that evolution was we became volunteer teachers inside of the prison. It was another max security prison that RTA works in in New York called Green Haven. We taught a film acting masterclass for several years and actually saw firsthand the power of this process… we went into a dark, dark, dark prison, and at the end of all of these gates closing behind us, you step into this classroom that is just full of love and light and a group of men who are so desperate to have access to new ideas and new opportunities and the creative process and workshops… We walked away just like, “If we can just capture the feeling of what it felt like in that room and then share that with the widest possible audience, then this will all have been worth it.”
 
The journey since then has been a big up-and-down roller coaster of trying to capture that feeling on the page. We failed a lot and wrote a lot of different versions of the scripts… [Through] getting to know two particular alumni from the program, Divine Eye and Divine G, [who] were so different from each other but, through the process of the program became closer than family. And I was like, “That's it. It's the story of a friendship.” Once we understood that, we were kind of off to the races and made it pretty quickly after that.
 
SING SING: Casting:
PR: I wanted to ask, SING SING stars a lot of people who aren't really film actors. What was the decision to cast people who were actually in the RTA program?
 
GK: It was very much a desire from the jump because we were introduced to the talent that was there... and there was something about when someone's telling you a story from their own experience and from their own voice... there is just a power to that… So that was always there, but we weren't sure to what degree we would do it.
 
Our previous film… we took three actors and brought them into this real-life racetrack and then integrated real-life jockeys and trainers into the storytelling. There were a couple of scenes that were so profound that I wanted to double down on this. How far can we push this approach? And so, with SING SING, you know, it became a central component of it, as you've seen, that the majority of our cast are from the formerly incarcerated guys who are playing like a version of themselves. The co-star of the movie is Clarence.
 
SING SING: Directing Actors:
PR: He is so good... When you're directing newer actors or newer film actors, do you take on a different approach than you would for professional actors?
 
GK: Well, I would say any actor has a process that helps, and I think it's important to be in tune with that and try and support that. The challenge in directing is [that] there are no two processes that are alike: You have to find some way for all that to be working in harmony… In this movie, in particular, the fact that that Colman is a highly established professional actor and a lot of our cast had never been in a movie before wasn't that incongruent honestly. And Colman especially was just a gift… he's a teacher at heart, and so, he very much was there in service of helping transition our cast to the camera; how to use it, and how to be in a scene.
 
SING SING: A24 Distribution:
PR: Now that SING SING has been picked up by A24, what happens now?
 
GK: The first thing that happens when you get acquired is you start to have initial vision conversations around like, “When is the release date?” “What other festivals are you going to play?” “Who could be various champions who could help lift the movie into the cultural conversation?”… It's all of these things that require a ton of effort and coordination... I think a lot of filmmakers aren't aware of what's required of them after they premiere their work and it gets picked up.
 
But, I really think a filmmaker's voice is really critical to kind of ensure that the core part of the movie is maintained, across all of its phases of life. Thankfully, I've been so amazed so far in the early interactions with A24… they're a company that is going to care for the movie with the same love and sensitivity that we made it with. That’s been very clear.
--

It's also been very clear after meeting with Greg what a kind, giving individual he is! Thank you so much, Greg for your time and expertise. Can't wait to see SING SING in theaters!