How ‘Sing Sing’s’ Creative Team Accurately Recreated Prison and Approached Designs With Great Sensitivity

Greg Kwedar’s “Sing Sing” is a one-of-a-kind film set in the prison of the same name. Rather than look at the broken justice system, the A24 film focuses on a group of inmates and their rehabilitation through the arts.

Colman Domingo stars as John “Divine G” Whitfield, a playwright who is incarcerated at Sing Sing for a crime he didn’t commit. He works alongside his best friend Mike Mike (Sean San Jose) and program director Brent Buell (Paul Raci) to build their acting group at the prison. Clarence “Divine Eye” Maclin plays a version of himself — someone with a knack for acting. Their prison acting group meets frequently to put on plays.

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The foundation is based on a true story and the success of the Rehabilitation Through the Arts program, which was founded at Sing Sing in 1996. That program has since expanded across New York state correctional facilities and includes dance, music and writing. But when it came to the world-building and telling this particular story, Kwedar and the film’s team of artisans were sensitive to the group of formerly incarcerated actors who play versions of themselves.

Kwedar says, “It was something we were very sensitive about and did not at all want it to be a re-traumatizing experience.”

The film’s costume designer Andrea Marks first sought advice from her sister, a psychotherapist, before approaching the actors. “I wanted to make sure that I was fully abreast of how to approach an individual who has this experience, and how to be both a great costume designer as well as a great listener.”

Marks put together a list of questions that she could ask Whitfield, Jose and Maclin, knowing it would be the first time they had worked with costume designers. She approached them as a friend, rather than a costume designer asking for personal photos. She also enquired about their relationship to what they wore, knowing she would have to put them in costumes.

She had a hard time sourcing actual prison uniforms since those are made internally, and even though she did reach out, Marks opted for Red Kap workwear that she then aged and distressed. The material was a blend of cotton and polyester. “It’s scratchy out of the box, so we softened it and made it better to wear.”

Production designer Ruta Kiskyte saw the world of “Sing Sing” as two elements: one of the prison reality and the other of the theater reality that existed within the prison reality.  Kiskyte wanted something authentic and natural, and that was a factor that was also important to Kwedar and the cast. “But what is unique about our approach, you see this prison that’s sunlit and pastel-colored, but there’s always barbed wire in the background.” Kiskyte continues, “It crushes your soul in much more nuanced ways than we expect to see in a prison movie.”

With prison, there was little way to express personality because of what is allowed inside. Kiskyte explains, “We really wanted to show how our main characters’ [prison] cells looked like — it was, interestingly, such a mind map of themselves. There was almost no decoration. Nothing was made to look prettier.”

Instead, Kiskyte took notes from Divine G himself and worked to be truthful in how she recreated the cells. She also wanted to convey how that theater was created almost out of nothing, with very minimal means to transform it into another place.