“We All Danced Out of That Theater Into the Night” | Greg Kwedar, Sing Sing

Colman Domingo and Clarence Maclin star in Sing Sing. (Courtesy of A24)

This year, the Chicago Film Critics Association is thrilled to kick off our 2024 Chicago Critics Film Festival with Greg Kwedar’s Sing Sing, starring Oscar nominee Colman Domingo (Rustin).

Screening Friday, May 3, at 6:30 p.m. at the Music Box, as part of this year’s opening-night selection (get tickets now), this story of resilience, humanity, and the transformative power of art stars an unforgettable ensemble cast of formerly incarcerated actors. 

At its center is Divine G (Domingo), who, while imprisoned at Sing Sing for a crime he didn't commit, finds purpose by acting in a theatre group alongside other men who are incarcerated.

Kwedar, who directed and co-wrote the screenplay with Clint Bentley, will be in attendance for a post-film Q&A along with stars Paul Raci, Sean “Dino” Johnson, and Clarence “Divine Eye” Maclin (who also holds a story-by credit on the script).

Ahead of Sing Sing playing the Chicago Critics Film Festival, Kwedar graciously took the time to answer this year’s CCFF filmmaker questionnaire. Below, his individual responses. 

How did you first become interested in filmmaking? What was your path toward directing your first film? 

I dropped out of my accounting major during my senior year, in the middle of an exam, to become a filmmaker. I was then convinced I needed to attend graduate film school so applied to eight schools, got rejected from seven, and was waitlisted for the eighth. 

I was doing a lot of humanitarian work on the US/Mexico border and conjured up a wild plan with some friends to get a better understanding of the people we were working with on the border. So we bought a 1973 Cortez bus, which was a former traveling puppet show, and set out to drive the entire length of Mexico and work in communities along the way. The bus broke down halfway into the trip, we all split up, and I ended up in Guatemala City, working with an organization around the Guatemala City Garbage Dump, alongside these single moms who recycle trash in the dump to care for their families. I was convinced that I was going to stay and make a film about these women... until, that night, I got a voicemail that I’d been accepted into film school. 

I came home and, two weeks before shipping off to school, I had a panic attack, thinking that the financial debt I was about to take on was too much. I called the school and said I couldn't come, because it was too expensive. They then offered me a scholarship. And I thought…”Well, something else is gnawing at me.” I was being drawn back out into the world, versus coming back to a classroom. 

So, I called the head of the school and asked if I was messing up my life by not coming to this very famous film school where so many of my heroes went. And he took a long pause and then said, "Honestly, you could be pushing a hot dog cart in Santa Monica and come just as close to becoming the filmmaker you're meant to be as if you came to our school." And so I withdrew and set out into that world, and the first short film I made was back in Guatemala with those amazing women. And the first feature I made was back on that US/Mexico border. Life is a circle. 

Greg Kwedar, director and co-writer of SING SING. (Courtesy of A24)

What inspired you to make the film you're bringing to the festival? 

I discovered this story eight years ago when I was producing a short documentary for a friend inside a maximum-security prison in Kansas. It was my first time behind the walls and, on a tour of the facility, I passed by a cell and saw a young man raising a rescue dog inside of his cell. And it stopped me in my tracks. In that one moment, all my expectations about prison and incarcerated people were flipped on their head. A lot of those expectations had been built upon the movies I had seen. 

I saw the healing that was happening in both directions between this man and animal. As I left, I was desperate to know who was doing things differently in prison, and literally typed, "who is doing things differently in prison" into Google in my hotel that night. 

Near the top of the search field was this program, “Rehabilitation Through the Arts in New York.” They had been covered in all the major press and had done all the classic plays, but there was this Esquire article about one of the few originals they had done: a time-traveling musical comedy called Breakin' The Mummy's Code. 

I was immediately convinced I had to do a movie about this program and the production of this wild play. I sent it to my partner Clint, and he too was in from the moment he read it. But that was just the beginning of the journey…

Tell us about a film that you consider a guiding influence (whether it has informed your overarching vision as a filmmaker, directly informed the title you're bringing to the festival, or both). 

Y Tu Mamá También, by Alfonso Cuarón, came out right when I was becoming a filmmaker and had a massive influence on me. I just felt like the world was able to breathe into that film. I didn't know a narrative movie could dance that closely with real life. It had this vibrant energy to it, and it seemed to be about the most simple things, like getting laid and finding a perfect beach, but it was also yearned for the deepest things, the stuff of poetry.

Tell us about a location that's held significance to the film you're bringing to the festival: a setting where filming took place, a geographic area that provided a source of inspiration, or another type of space that comes to mind for you in thinking about the film. What made this place so special? 

Sing Sing itself. It’s one of our most iconic prisons. The term "the big house" came from Sing Sing, and going "up the river" to prison was a phrase coined from the barges that used to carry people up the Hudson River to be incarcerated at the prison. 

It’s one of the only prisons in the world where a commuter train travels through the yard, a constant reminder to the people inside that the world is moving on while they are staying in one place. And yet, despite the razor-wire and the walls and the trains that rumble through, the men in this program created staggeringly beautiful art. 

The theatrical experience brings us together to celebrate artistic experience and expand our horizons as human beings. Tell us about a memorable theatrical experience from your life. 

Clint and I were in Deauville, France, for the film festival there, with our first film Transpecos, and we caught a screening of Sing Street. It was a theater with 2500 people and, as the final scene played out and the credits began, the audience was on its feet, clapping in unison to the music. We all danced out of that theater into the night. 

Sing Sing screens Friday, May 3, at 6:30 p.m, as part of the Chicago Critics Film Festival (May 3–9, at the Music Box Theatre in Chicago). Get your tickets now.