The Rehabilitative Power of Art in Sing Sing
Oscar nominee Colman Domingo teams with Austin filmmaker Greg Kwedar in a story of transformation behind prison walls
By Richard Whittaker, Fri., Aug. 2, 2024
Sometimes a film feels like more than just a film, and in being so becomes less of a film. Sometimes a movie gets bogged down in the self-importance of its message.
And sometimes there are films like Sing Sing, the latest from Austin-based director Greg Kwedar and his co-screenwriter, fellow Texan Clint Bentley. There is no overt call to action in their drama about Rehabilitation Through the Arts, the theatre program for inmates at New York’s notorious Sing Sing Correctional Facility. Instead, the film glows with an inner light that illuminates what the program has meant to the men it has helped heal. “It smashes tropes about the people inside the prison industrial complex,” star Colman Domingo says. “They found how art helps them transform and heal.”
Kwedar’s first movie also looked at the legal system, but from the other side of the process, as dusty noir Transpecos examined the day-to-day grind of life as a Border Patrol agent in Texas. It was a small production, basically a three-hander shot on location, and far removed from the experience of Sing Sing. Since its premiere at last year’s Toronto International Film Festival and through its current release by A24, the film has already been talked about as one of the year’s most impactful. “Aw, man,” Kwedar laughs over Zoom. “It’s wild. Just to be in a hotel room that’s dedicated to interviews? Come up in the world.”
It’s been an even wilder ride for Bentley, Kwedar’s longtime creative partner, who is balancing press calls for Sing Sing with pickup shooting in Washington state for Train Dreams, the new film he’s directing starring Joel Edgerton and William H. Macy. “We’ve been working on this film for eight years,” he says. “I’m glad that we’re getting to elongate the process so much because I get to stay in interaction with the film.”
There’s a sensation around Sing Sing. Kwedar recalled walking around New York City a few days after the film had wrapped, “in this strange, delirious daze of being aware that this feels bigger than us already.”
But he’s not talking about himself and his career, or reviews, or box office. As Domingo (an honorary Austinite after filming three seasons of Fear the Walking Dead here) explains, “It feels like we’re putting a film out into the world, and it’s becoming a movement. It feels like a big, open heart being put out into the world, and it’s being received as such.”
For Kwedar, this all comes back to the idea of transformation. “You hear the words 'Sing Sing,’ you think of prison,” he said. “Through making this film, if people around the world can hear the words 'Sing Sing’ and it becomes synonymous with art and community and joy, that inherently felt like such a rebellious act, and thrilling to contemplate.”
Becoming Yourself Onstage
In Sing Sing, that community and joy flourishes on and off the RTA stage in the true-life story of the friendship between one of the troupe’s oldest and most committed members, award-winning writer John “Divine G” Whitfield (Domingo) and newcomer Clarence “Divine Eye” Maclin. It’s a revelatory screen debut from the real Maclin in the part, but far from his first performance. After all, he, like many members of the cast, is playing a version of himself, inspired by his own experiences as a member of RTA and by his own time behind bars and on the stage at Sing Sing.
Their presence gives the film the kind of lived authenticity that is impossible to replicate, much as Bentley experienced when he used real people from the world of horse racing for his directorial debut, Jockey. “We saw how much that film came alive and was so much better by using the real people from the track. ... It was clear from early on that there was nothing we could write in terms of what these guys could bring on a daily basis.”
Make no mistake, says Domingo. Those RTA veterans are no less actors than he is. “It is a craft, and you can get your training anywhere,” he explains. “You can get it at Yale, or you can also get being a journeyman actor like me. ... They got their conservatory training six months out of the year in an institution with the RTA program.”
Those same RTA alums were also the people who gave Kwedar the greatest confidence in the film. “You talk to any of the alums in our film, and they’re like, 'Oh, yeah, this is going to be worldwide.’ That kind of confidence was so infectious and helped carry you through the roller coaster of bringing this to the finish line.”
From the Rio Grande to the Shores of the Hudson
It was around the time of Transpecos that Kwedar first read an old Esquire article by John H. Richardson, “The Sing Sing Follies (A Maximum Security Comedy).” In it, he found out about the world premiere of a time-traveling screwball comedy play called Breakin’ the Mummy’s Code. However, it wasn’t just mounted on any stage but at one of the most iconic prisons in the world: Sing Sing. The 198-year-old prison 30 miles north of Manhattan has defined the American popular image of a prison. It was the original Big House, literally the genesis of slang like “getting sent up the river,” and there have been so many films and TV shows shot there that Warner Bros. built a soundstage on the property in the 1920s. However, it is also where Rehabilitation Through the Arts began. In 1996, marketing executive Katherine Vockins started visiting the prison when her husband began teaching there. She followed suit by giving up her job to help a group of inmates, dubbed the Theater Workshop, to write and stage a play called Reality in Motion, a study of their lives and experiences inside the penal system. The play was such a success that they did it again, and again, and again. Since being renamed RTA in 2001, the program has spread to five other prisons around New York and has had astounding, life-changing results.
The numbers don’t lie. Nationally, 60% of people released from prison return to jail within three years. In RTA alumni, that reincarceration rate drops to 3%. But more importantly, it’s a space – as one character in Sing Sing explains – in which they learn how to be people again.
While Kwedar knew immediately this was a story he wanted to tell, he wasn’t sure how to tell it. The early pitches, he admits, “were jumbled, especially when you’re trying to pitch it to the cast, and to our alumni cast particularly. 'It’s about a play that you were in at one point in 2005, and you were doing the play, but it’s not really about the production. It’s really about you guys and the community, and you’re playing a version of yourself, but not really yourself, and there’s a script, and then there’s unscripted moments.’”
Domingo explained that when Bentley and Kwedar first approached him, they didn’t have a script yet. Instead, they had what he’s always looking for in collaborators: “A curiosity and a kindness and a great work ethic and the possibility of creating something unique together. It felt like they wanted to build a community that I wanted to be a part of.”
Both Bentley and Kwedar recalled that early drafts lacked focus. According to Kwedar, there was a dearth of “characters that you could really attach to,” while Bentley recalls that “they were either too broad and inaccessible” by trying to cram in the entire ensemble, “or too narrow and just focusing on one character and their journey through that space, but feeling like that, in focusing on that one character, you’re missing so much that they’re not experiencing.” However, they always knew exactly what kind of story they were telling. Bentley explains, “It wasn’t like in some iterations it was super-violent or a heist movie. The tone was always there, and we just couldn’t seem to find the right storyline with it.”
Knowing the tone made it easier to avoid the tropes of prison movies, like evil wardens and breakout schemes, that had no place here. Kwedar recalls, “We would get notes from development executives wanting us to put that stuff in here. They’d be like, 'I know it’s a cliche, but audiences need that,’ but it felt like it would cheapen it.” Moreover, those tropes are just not real. “When we would talk to the guys, they would complain about them and say, 'That’s just not how it is.’”
For Domingo, that openness to discovering what the story should be was a positive, especially as Kwedar didn’t walk in the room with the conviction that he had all the answers. “He’s liberated himself,” says Domingo, “to say, 'It’s OK if I don’t know, because I’m surrounding myself with people who are curious to find out.’” Equally, knowing he would be working with an ensemble allowed Domingo to liberate himself from the bolder, big-swing performances that made him a standout in films like Zola, The Color Purple, and Rustin (for which he was nominated for an Academy Award this year). “I want to fade in with my fellow colleague in this film. I didn’t want to stand out as, 'Oh, people know my work.’ I need to be a part of the ensemble and give room for other performances that are mighty and gorgeous and find space to play the notes that I need to play.”
That egalitarianism was built into the final script, which Bentley describes as having three components. There is the traditional story structure, but within that there are also places designed for improvisation, to allow the same playfulness and discovery as RTA nurtures in rehearsals. “It was about making space for what we knew would be very magical. Whatever they did would be better than whatever we could script.” On the page, those moments almost read like improv prompts, such as when play director Brent (Paul Raci) asks the troupe to describe a perfect place. “It’s only two lines on a page, but it winds up this magical six to eight minutes on the screen.” Finally, there are the scenes from Breakin’ the Mummy’s Code, taken straight from the original script, and that was the easy part. “It was bonkers enough as it is. It doesn’t need any embellishment from us to make that play crazy.”
Over time, the creative team homed in on a simple yet rich narrative core of the complicated relationship between Divine Eye and Divine G. As the filmmakers spent time observing their bond, “it clicked,” says Bentley, not least because it allowed the film to explore both sides of the RTA experience. “You could get the newcomer who’s never seen this program before, and it seems kind of silly at first, and then you have the more seasoned veteran who knows the power of it and knows the ins and outs.”
According to Kwedar, what made their bond stand out from all the other relationships forged in RTA is “this very real friendship of these two men who couldn’t have been more different from each other but because of this circumstance became closer than family.”
The nature of their friendship is all the more remarkable because of where it happened: in a maximum-security prison, which Bentley calls “the darkest of rooms. .... What they’re creating in there is such a source of light and optimism that’s so affecting in a way that’s hard to put into words.”
Playing at Being Real
Sing Sing is inspired by real life, yet not wholly biographical, so while Domingo was still able to talk to the real Whitfield, “it wasn’t like I was interrogating him. I did not want to pry into a person’s past life. ... We just had conversations, and I observed and downloaded some information about him that I was able to translate into action and story. The fact that he was always in the law library and he was a founding member of the RTA program, for me that tells me how much of a hopeful person he is. ... He was actively doing the work in a kind and gentle way, and I wanted to show that on film, too, give a sense of how gentle that program is.”
There’s a word that is said repeatedly – beloved. That’s how the members of the program refer to each other. “It’s a transformational word,” says Domingo, as summed up in a scene when Whitfield explains to Maclin that’s what the RTA members call each other. “He has a choice, to receive it or not. And he stares at me for a long time, and I love that stare when I watch it in the film – Clarence does beautiful work – and in that stare I watch the word being used on him. He has the opportunity to transform, because that’s what his brother in this program is offering him.”
At the same time, Domingo knew that Divine G could never feel like “a martyr” and that there are hints at the toughness he would have developed to survive in the brutal environment of Sing Sing. More importantly, Domingo knew that Divine G needed just as much room for growth as Divine Eye. “His Achilles heel [is] that he always felt that he was smarter than everyone, that he knew best, that he was doing the work for others but didn’t know how to receive help as well because he didn’t like that position and it made him feel weak.”
Moments of openness, of emotional vulnerability between men, are rare in films, but for Domingo they were the key to telling the story. “I said to Greg early on, 'We need to show images that are about tenderness in this community,’ because that’s what they told me. ... To watch a man hold another man’s hand or embrace another one and have space to be vulnerable and fall into their eyes with a cry. What a powerful image, to say we don’t have to support these toxic masculine identities that we always have to play into.”
Behind the Camera, Behind the Wire
Just as the real men of RTA informed Sing Sing, so did the real prison. Kwedar was able to film exterior shots at Sing Sing itself, and those exteriors helped shape the film, because Sing Sing is such a place of contradictions and juxtapositions due to its location. “You have the rolling hills and how green it is, and that is surrounding a place of steel and razor wire and stone,” says Kwedar. But he was equally fascinated by Metro-North Railroad’s four-track Hudson Line, which runs literally right through the middle of the complex. The inmates do not simply see it, but hear and even feel it as it rumbles past. Kwedar says, “It’s this constant reminder to everyone inside of the world moving past them, but they’re still staying in one place.”
While Sing Sing was available for exteriors, it’s still a working prison. Luckily for the production they were able to use the recently closed Downstate Correctional Facility, 50 miles up the Hudson. Kwedar learned that every member of the alumni cast had been incarcerated at Downstate “at some point in their journey.” Indeed, the cell used for the fictional Clarence Maclin was literally right beneath his real cell from his time there. Kwedar explains, “We were very cautious and nervous of whether this would be a retraumatizing experience for our cast. What I wasn’t prepared for was how even just putting prison greens on could resurface that pain. But the transition that started to happen – that now this was our set and this belongs to us, and this was our space to create and to tell their story, and they were now a character, and these greens were now a costume that they could take off freely – really became a catharsis for our actors.”
That’s part of why the film never really looks at case histories of individual inmates. Bentley notes that in doing so the script avoids defining them by one act or moment in their life, and Kwedar concurs. “People find themselves incarcerated for a myriad of reasons,” the director observes, “and you can get lost in arguing what is driving that person to be there. Yet regardless of how someone arrived there, they’re there now. And it’s what now? What next?”
Kwedar feels the film is inspired by the program’s philosophy of being present, of being in the moment, of forgiving your former self without forgetting the past, of not letting one past moment – whether it be a crime or a conviction – define who you will be tomorrow. It’s why, much like Breakin’ the Mummy’s Code, Sing Sing deals with time, and Kwedar recounted the idea that some of the former inmates had told him: There’s “slow time, when you almost want no representation of it – no clocks, no watches – and it feels like it’s just melting off you. Then there’s fast time, and it’s the kind of time you wish you could slow down, which is when you’re inside of this space and doing the work ... you blink and it’s years that have gone by.
“What’s beautiful about this program,” he adds, “is that, rather than it just being time that’s stripped away, they find meaningful time.”
Programs like this are always in peril, always having to justify their worth in the face of budget cuts and a twisted belief that art isn’t essential. That’s an attitude that seems to permeate much of American political culture, and it doesn’t stop at the prison gates. In education circles, it’s an accepted fact that art and theatre are the first budget items to be cut, while conservatives are waging outright war on public libraries. “Anywhere people have access to art, they thrive,” says Kwedar, “and the case that this movie is making is that, if inside of all these walls and all this razor wire, if art can be created here and these people can flourish here, then surely it can and should be accessible anywhere.”
Bentley concurs, adding that this isn’t just about the time these men spent in the program, but what continues when they leave. “They’re so open and raw because they’ve taken off their masks as people that it pushes you to be a better person.”
If nothing else happens with Sing Sing, Kwedar hopes that it will make audiences reconsider what they think when they hear words like “inmate” or “prisoner.”
“It doesn’t have any direct agenda except for asking an audience to meet our cast at eye level, [and] once you do it’s impossible for these people to be anything other than full human beings.”
Sing Sing will be released in Austin on Aug. 9.
