The story behind Greg Kwedar’s poignant drama Sing Sing is as compelling as the film itself, with costume designer Desira Pesta and production designer Ruta Kiskyte deeply understanding the scope of this unique project. The film weaves the real-life experiences of formerly incarcerated individuals who participated in the Rehabilitation Through the Arts (RTA) program at Sing Sing Correctional Facility.
“I did so much research and picked apart every Department of Corrections website,” shared Pesta. “But only through talking to [the cast] was I able to really glean how they differentiated themselves and how they expressed themselves.”
Sing Sing delves into the experiences of John “Divine G” Whitfield, portrayed with heartfelt intensity by Colman Domingo. The film includes a number of non-professional actors and draws inspiration from a 2005 Esquire magazine article about an ensemble comedy performed by inmates at Sing Sing. It premiered to critical acclaim at the South by Southwest Film Festival, where it won the Audience Award.
Both Pesta and Kiskyte recreate the prison environment with meticulous attention that helps the audience immerse into prison life while reflecting the personal histories and emotions of the cast. The film’s production, shot in an actual prison, adds a level of realism that enhances the narrative.
“Everything you saw and things that you couldn’t even really see in the cell, everything was based on research and really extensive talks with our formerly incarcerated cast,” explained Kiskyte. “Nothing was really dressed for show in a classical sense of a movie. Our goal was to make it as authentic and as real as possible.”
Desira Pesta and Ruta Kiskyte spoke with Awards Focus about what they took away from the experience of working on the film, how the cells were dressed to replicate those of the formerly incarcerated cast, and how the positive energy on set enhanced the film’s production.
Awards Focus: I wanted to start with a question for both of you. What did you take away from the experience working on ‘Sing Sing’?
Ruta Kiskyte: First and foremost, I feel like everyone walked away from it just being a better person. Professionally, it resuscitated my belief in this industry and made me love my work so much, and reminded me why I’m doing this. I think it reverberated through the whole crew. I recently read this note from a production assistant about how working on this film made her stay in this industry.
Desira Pesta: I just got goosebumps a little bit because I think experiencing this project, through meeting the people involved who actually lived the story, and then getting to share that again with them, is something that is indescribable and so special.
We felt it palpably throughout the entirety of the shoot as much as we were working hard. I think all of our hearts were softened and touched, and it just like really bonded us in a way that is hard to describe, but it was just really special.
Desira, what was it like to fill out the costumes for each of the individuals, given their involvement in the program and finding their personalities within their clothing?
Pesta: It was wonderful in that I got to actually speak to and ask questions of those who were acting. That was something that I’d never encountered, so I did a lot of research. It’s hard to really get a handle on what happens inside unless you’ve been there. I did so much research and picked apart every Department of Corrections website, and we watched documentaries, but only through talking to them was I able to really glean how they differentiated themselves, how they expressed themselves, and what choices they made with what they were given.
Were the conversations with the actors about generating looks that were accurate to their experience or were they identifying with the character being played in the film?
Pesta: I think it was a little bit both. It depends on the person we’re talking about. Either they went in wanting to fully relive or honor the reality of what they did when they were inside. I think for certain people, I’ll just keep to myself that this was maybe the only safe way to enter back into the prison. Then we aged everything. It was all new costumes; we aged it, distressed it, and tried to honor how long each person had been there.
For you, Ruta, there’s a distinction between using a built set and using somewhere that’s already established. I’m curious about the conversations that led to filming in a real prison rather than in a built set.
Kiskyte: Shooting inside the prison, which was, in our case, the Downstate Correctional Facility, was something that our director and producers, Clement Lee and Monique Walton, had researched, and it was one of the first things they did once the production kicked off because they knew they wanted it to be grounded and set in inside a real facility. But there are just so many places you could shoot something like this, and shooting in the real prison from the story was not possible at all because it’s like a functional prison. We were at the tail end of Covid, so we were only able to get some exterior shots, and it was really just a skeleton crew.
All the cards just fell into place. That Downstate Correctional Facility was decommissioned weeks before we entered it, and they got permission to shoot there. And even though it’s not the real Sing Sing prison, it’s a place where most of our cast served time because it was a processing facility. So, they went there before they went anywhere else. Divine Eye actually served time in a cell right above his characters’ cell.
The cells had different shapes and contours, like Divine Eyes, which is a triangular shape. Did that affect how you were designing each of the cells?
Kiskyte: Everything you saw and things that you couldn’t even really see in the cell, everything was based on research and really extensive talks with our formerly incarcerated cast. We spent so much time talking with Divine Eye and Divine G, who’s played by Colman Domingo, and really recreated what they had, even though those cells were a little bit bigger than what they had at Sing Sing. Nothing was really dressed for show in the classical sense of a movie. Our goal was to make it as authentic and as real as possible.
The play features a large amount of costumes. Where did you source the different costumes, and how much were you replicating what had been used in the past?
Pesta: That’s a great question. We wanted to honor the ingenuity of the real plays. I think there was just so much that they put into it that I thought it would be a travesty not to try to replicate or try to have certain pieces. So, with that said, we watched the entirety of the original production, which was videotaped, and combed through all the photos. I kind of pinpointed what I thought was awesome but could be elevated for the screen. Then, it was what was feasibly possible to procure with the resources we had, which were not a lot. We had the great benefit of going to the same place where they had been able to borrow a few things 20 years prior.
A group of us, including Paul Raci, just went through this giant facility and somehow came up with a few things that had either been in the original, and I’m talking like they didn’t put it off on the side and say, this is saved for RTA. This was a student costume shop. So, we were able to find a few things that were amazing and then a few things that were not original to the production but could work. All the Hawaiian shirts that are in the pirate scene had been saved for 20 years. They were in a box. So, those were brought back out and we just tried to obviously amplify a little bit of it for the screen.
Before the dress rehearsal, there’s that one-shot behind-the-scenes going through each character as the camera moves around backstage. What was it like preparing for that scene, dressing up the backstage, and the chaos that’s happening before the dress rehearsal?
Kiskyte: Thank you for noticing that. It was an epic shot, really. We just rehearsed it so many times, and thanks to our first assistant director, Michael Toscano, he was really the ghost orchestrator of that shot. We made do with everything we had and dressed around the perimeter of that stage and inside the stage. So, it was really truthfully what was there for the play itself.
It’s interesting because that gives the film a documentary feel. For you, Desira, what was that scene like, having all the characters dressed in their costumes for this scene?
Pesta: We had a team of two for 20 of the 22 days. It was very cinematic and had an incredible array of amazing things that were captured on film. These were all the costumes that were in the real production, so we knew that eventually, we would do these vignettes. Everybody had something.
My favorite costume was the guy in the tower who had a long mop of dirty hair, and he’s in that great tower that Ruta and her team made. He had all these chains on, and that costume weighed like a hundred pounds. We made that out of mops because it was cheap, and it made sense that they could have made that.
What was the energy on set like on those days with all the men revisiting and replaying this version of their experiences?
Kiskyte: Oh, incredible. We drew inspiration from them, really. There was such a range of emotions, and they were also super supportive of each other because some of the stuff that they had to go through or revisit was really emotional. It was incredible to see how they would if somebody was going through something; they would dart to that person and go and support them. When you spend time with them, you understand how much guard you have up when they’re just so open to the world and to each other. It just makes you want to step up in terms of the production of the film.