The Imagination Flies Free in Sing Sing’s Maximum-Security Prison

Colman Domingo stars in a drama about the redemptive, reawakening power of art in a prison theater program.

Out of sight, out of mind is how most Americans probably think about incarcerated individuals—until an acquaintance or a loved one lands in a correctional facility, after plotting a crime or perhaps just acting impulsively in a heated moment. It’s easy, and comfortable, to pass judgment. But Greg Kwedar’s true-to-life prison drama Sing Sing asks more of us: If we believe in our own capacity for growth and change, how can we not extend that good faith to other individuals who have made mistakes?

Colman Domingo stars as John “Divine G” Whitfield, serving time at the infamous New York prison Sing Sing for a crime he didn’t commit, though he’s hopeful that an upcoming clemency hearing might clear his name. In the meantime, he’s become deeply invested in a prison theater program, not only performing but also serving on its steering committee, helping to determine who joins the program and what productions get mounted. He’s also written a play himself, one that he hopes might someday make it to the stage.

He and his closest friend Mike Mike (Sean San José) are always looking for new men who might benefit the group—and benefit from it. They approach Clarence “Divine Eye” Maclin (a real-life alumnus of a similar arts program, playing himself), who has a reputation as a tough guy around the yard. Divine G knows his instincts about Divine Eye are right when the latter rattles off a passage from King Lear, proving he’s taken the play to heart. But it takes a while for Divine Eye to recognize that part of the troupe’s aim—which it achieves through a mix of acting exercises and just plain yakking, led by the group’s coach, Brent (Paul Raci)—is to get the men to explore feelings they usually keep locked down tight. He resents Divine G’s efforts to help him open up, and the two clash, though Divine G’s ego is part of the problem too.

Prisons are self-contained societies, and Sing Sing underscores just how complicated interpersonal relationships can be when you’re being watched every waking and sleeping moment. Even the movie’s production design suggests how these men strive to preserve their individuality: their cells’ narrow windowsills might be stacked with books or small boxes of favorite foods; the drawings they’ve hung on their walls may have been done by their kids, or by themselves. Even the smallest assertion of self has meaning and value.

Kwedar co-wrote the Sing Sing script with Clint Bentley (the duo also made the affecting 2021 drama Jockey), and the story they tell is drawn from the real-life Rehabilitation Through the Arts (RTA) program. The film features several actors who got their start through that initiative, including Maclin. His performance has a nervy kind of electricity: Divine Eye has been bruised by life, and by the system, but we can see his desire to climb back into the world as a new person, a more open and self-aware one. Domingo gives Maclin all the air and space he needs to create that character. That’s what a truly terrific actor does: he steps back and listens, instead of merely relishing his own lines. 

And even if Sing Sing shoulders some heavy-duty ideas about forgiveness and redemption, Kwedar also recognizes the value and delight of pure play. The troupe prepares a nutty, clever comedy Brent has written for them (adapted from a work that real-life RTA teacher Brent Buell developed for his students) that’s peopled with pirates, Egyptian kings, gladiators, and more—basically, a part for everybody. To watch this movie’s actors, many of them playing versions of the men they used to be not so long ago—to see them incorporating classic pop-locking moves into their swordplay, or tinkering with the phrasing of Hamlet’s soliloquy until it rings true to their experience—is to witness a cautious but joyful reawakening. If a group of forgotten men can pull this sort of thing off, then what excuse do the rest of us have? Outside prison walls or within them, those who stop growing have only themselves to blame.