“I’m going to make you cry,” Colman Domingo promised as he sat down across from his “Sing Sing” director Greg Kwedar for the first conversation in TheWrap’s Visionaries video series. The Oscar-nominated actor from “Ma Rainey’s Black Bottom” and “Rustin” said his days as a journalism student would come in handy during the hour-long conversation, in which the two men got passionate and emotional as they discussed what led them to their careers and what led them to the indie gem “Sing Sing.” (Spoiler alert: Kwedar did cry, but Domingo cried first.)
The film is a moving and compassionate drama set inside Sing Sing Correctional Facility in New York and focused on a group of inmates in the prison’s real-life Rehabilitation Through the Arts program, in which incarcerated men put on theatrical productions. It’s based on an actual production and features a mixture of professional actors — Domingo, Paul Raci — with formerly incarcerated men who were once part of the RTA program themselves, including Clarence “Divine Eye” Maclin, who’s won raves for playing a character based on himself.
While the film would be entertaining and touching regardless of its backstory, it’s also startling for its financial model: Every person who worked on the film, from Domingo to the dolly grip, was paid the same flat rate, and everyone has an equity stake in the movie.
TheWrap’s new Visionaries series will pair collaborators, colleagues and competitors across the spectrum of films and crafts. This discussion is edited for length and clarity.
COLMAN DOMINGO The way you tell story and the way you bring people together is unique. Where does that come from?
GREG KWEDAR Well, both my parents had jobs, but their passion was they were coaches. My dad was a rugby coach, so it was about being part of a big team. My mom was a golf coach, and her point of view was more a Zen thing of “You’re not playing an opponent, you’re not playing the course, you’re playing yourself.” I lived among many sports metaphors my entire life. (Laughs)
DOMINGO It’s now making more sense. You do like the idea of a team (where) everyone has a job to do.
KWEDAR And within that was the future of being a storyteller. I think the seeds were there. I wanted to be a doctor when I was a kid, so I would take my stuffed animals and cut them open and put things inside them and sew them up with my mom’s sewing kit.
DOMINGO OK. That’s a little dark, though.
KWEDAR When you say it out loud. (Laughs) It seemed like I was on the path to being a surgeon, but it was actually more psychopath.
DOMINGO (Laughs) The same thing in our industry.
KWEDAR But in hindsight, I was more interested in the story and the creativity than the profession itself. And in junior high school, my AP English teacher, Mrs. Smith, read an essay of mine and said, “You have a voice. Keep writing.” But I pushed that aside for many years. I went to college and I was an accounting major.
DOMINGO I feel like we owe a lot to the Mrs. Smiths in the world. My first acting teacher told me I had a gift. I’m not knocking my parents, who were such loving, caring parents, but no one told me I had a gift in anything. But that one person says, “You have a gift.”
KWEDAR Did it resonate right then? And did that alter the course of your life?
DOMINGO It did. I was a journalism student at Temple University, and I grew up very shy, very bookish. I was a bona fide nerd. I went to college and I wanted to write. I wanted to go to war-torn places and write about it. I wanted to be that kind of journalist. I was concerned about the world and wanted people to know what was going on. My mother early on always inspired her kids to take part: “Don’t just sit back, do something about it.”
But when I was at Temple, I took an acting class as an elective because I was so shy. And my teacher pulled me aside towards the end of the semester and said, “Colman, have you thought about acting as a profession?” And I thought, I don’t even know what that is. How would I do that? So I said no. He said, “I’d be very curious if you pursued this path, because I believe you have a gift.” And that changed my whole DNA in that moment.
KWEDAR It honestly took a while for me. That message from my teacher was something I shrugged off for about five or six years. I was chasing those prescribed paths that you get ushered into when you enter college. I got into accounting just because it was the prestigious program in the school and it was a guaranteed job. And actually, I was on the precipice of accepting a job in accounting. I was in New York. I had put on an ill-fitting suit to go to an interview in the financial district, and I was on the 50th floor of this office building, looking down onto the ruins of the World Trade Center. The memorial hadn’t been built yet. And after my interview, I walked uptown from the financial district. I was in Washington Square Park, around all these artists: people selling weed and other people reading books and other people dancing and all that. And I was like, “I love this city, but I don’t want to be in a city wearing this suit.” That was the moment that was starting the break from (accounting).
That summer I was in Sydney, Australia, playing sports. I was in a café and I pulled out a notebook instinctively. The voice of my teacher started playing in my head, and I just started to write. And then I looked up this film school in Sydney. I got a tour of the facility, and in the basement, these two women were casting their short film and they handed me the sides (and said) “Hey, can you read for the actors coming in?”
So I read for a couple hours and then after we finished, they were like, “Hey, we’re shooting in two weeks. We need a PA. Will you come?” I was like, “I don’t know what that is, but yes, I’ll be there.” And once I stepped onto that set and felt the energy of all these artists working together, I was like, “This is for me.” I went home and dropped out of accounting.
DOMINGO Wow. Are you good with accounting and books?
KWEDAR It helped shape my entrance into this business. I was seeing a lack of transparency and I started looking at the process. That then led to Clint Bentley and I, years later, developing the financial model that’s behind “Sing Sing.”
DOMINGO That’s phenomenal. I love the fact that I’m just finding this out.
KWEDAR A lot of times people think that these chapters of our lives (are separate). But everything accumulates. Everything is a tool in your belt that you can use.
DOMINGO This is something that a lot of young artists don’t understand. They don’t look at all of those things as being part of the makeup of an artist. But it is. I know that me being a bartender for 15 years is very much a part of the way I know how to talk to people.
KWEDAR How much time did you spend bartending while you were a working actor? How long before you were able to let this fully sustain your life?
DOMINGO Yesterday? (Laughs) Honestly, I had always found it was best for me not to have a 9-to-5 job. I always needed a job that was flexible. So I started off waiting tables and then I moved into bartending because you had a bit more power at the bar. The world circled around the bartender. But I always taught as well. I would coach people on their monologues for auditions, you name it. I also had a side hustle doing headshots. Oh, I was a great headshot photographer.
I always had these flexible jobs, bartending and things. Bartending was my favorite because I love talking to people. I’ve had some of the most profound conversations and moments in my entire life at a bar.
KWEDAR Do you remember any of those conversations?
DOMINGO I can tell you one in particular about my friend Rodney. He was a homeless guy who would come in every night. We closed the bar about 4 o’clock in the morning. He would usually come in about 3:15, 3:30. This was a very small bar in the West Village. He would come in and put up the chairs and sweep. And we would pay him $5, $7. If we made a lot of money that night, we might tip him $10. He had a limp, he had a really bad leg and he always looked terrible.
And this one night, he came in. It was a cold, cold winter night. I was going through my stuff as an artist. I wasn’t booking work. Both my parents were ill. I was having a really hard time. I get emotional thinking about it. He came in, and something was going on with him, too. And we were both very quiet that night. I was playing Donny Hathaway’s album, and he was sweeping, putting up chairs. I got him a ginger ale (because) he liked ginger ale with bitters in it. I’m singing this Donny Hathaway song, “Someday We’ll All Be Free,” and I hear him singing it as well. It (went from) a solo to a duet to a trio. We sang at the top of our lungs, and we both were crying. And he was like, “Thank you for that. Thank you.”
I feel like it’s cinematic because cut to: I didn’t see him for months. And I didn’t know what happened to this man. One spring evening the door guy says, “Hey Colman, there’s somebody who wants to see you.” I go out and it’s Rodney. He’s cleaned up, he’s in a wheelchair. He looks like a young college professor. He said, “I can’t thank you enough. After that night, I went home to D.C. to my family. I told them I needed some help. And it was hard for me to finally get to that, but there was something that happened that night.” (Pauses, wipes eyes)
He had one of his legs amputated, and he was on the healing path. And literally, it’s the last time I saw him again. I don’t know if we had a lot in common, but we had our humanity in common. We had music in common. And we just shared this open-hearted moment.
KWEDAR I love your heart.
DOMINGO Oh, thanks, man. Yours too. I’m surprised I cried before you! (Laughs)
KWEDAR I was thinking about that as you were telling the story. I was like, “You first!” No, but it’s indicative of the whole conversation. We’re talking about moments where you pause and actually engage.
DOMINGO Like that moment when you were (shooting in a prison) and you saw a guy working with a rescue dog. That little moment changed your trajectory and helped you create Sing Sing, right?
KWEDAR Yeah. I was producing, I wasn’t directing, and we were making a short doc. It was my first time ever inside of a prison in Kansas. Because of all the stereotypes around prison and incarcerated people, your body is operating on a lot of fear and anxiety. But on a tour of the facility, when I saw that young man in that cell, I think the reason it stopped me in my tracks was because it was so decidedly against the current of all those expectations. What was happening in that room, and it’s a word we used often through the journey of this project, was healing.
DOMINGO And care. I think most people never associate that with folks that are incarcerated.
KWEDAR Right. That’s profound. What was it like, first hearing about this project?
DOMINGO I’ll be very honest, I didn’t know what I was getting myself into, really.
KWEDAR Well, there was no script. (Laughs)
DOMINGO No script. But even reading the article (about the RTA program) you sent me from Esquire magazine, I thought, these guys are holding a space of tenderness in such a dangerous space for that, where they’re absolutely not supposed to be vulnerable or open up their hearts or talk about their feelings. I thought that was extraordinary, maybe (because of) my own work as a man to connect with other men and tear down the walls of all this toxic masculinity because it doesn’t serve anyone. It doesn’t serve our families, it doesn’t serve our communities, it doesn’t serve our partners.
KWEDAR What’s so radical about this program and our film is that prison has become very effective at defining someone by a single moment in their past. Our movie is about allowing us to feel them in the fullness of who they are. We can be vulnerable and share the moments of our lives that have made us as well as start to have a shared imagination of who we can become.
DOMINGO I don’t even know what’s next for you. Are you gonna try to take some of this energy into it, or are you directing the next Marvel film?
KWEDAR (Laughs) Well, I think it really depends on how many of them will get to star Colman Domingo.
DOMINGO Perfect answer.
KWEDAR I mean, I think making “Sing Sing” has set this whole new standard. Not just for “Is a movie good or not?” but how you feel when you’re making it. And I just want to feel like we felt, as well as how I feel when we share this movie with the world. I think “Sing Sing” is a movie about hard-won optimism. I think we need more of that in our world, and I want to be a part of telling stories like that. What about you?
DOMINGO I feel the same way. This is gonna sound a bit like a Pollyanna, but I do mean it: I want to love the people I work with. You and I, we love each other, and I love Clarence and I love the cast and crew. It’s not about what you can get from something. It’s what can you give to it to be of service. It’s about the collective. It does feel somewhat radical, because the nature of this business is a little selfish, you know?
This story first appeared in the Race Begins issue of TheWrap’s awards magazine. Read more from the issue here.
