What Sing Sing Teaches Theatremakers

Leaving the District of Columbia Central Detention Facility every week was, in some ways, more tiresome than the obstacle-laden process of getting in. In 2022, as a fellow at Woolly Mammoth Theatre Company, I had the unique privilege to be a member of Spit Dat Academy at the jail, a weekly spoken word poetry workshop with incarcerated poets. The program culminated in a poetry reading inside the jail, bringing together an audience of people from inside and out. For a young, aspiring theatremaker like me, this program was an invigorating example of the power of art to connect people across structural barriers, like jail walls. At the same time, it was a sobering, routine reminder that some of the greatest artists of our time remain confined within those walls, literally barred from sharing their work with the world. On the red line back to my Maryland apartment, it passed through me—the tension between the profound impacts and undeniable shortcomings of our collective endeavor. Poetry cannot demolish the walls, I thought, as the metro jostled me into an erratic sway. The walls cage the poetry, I thought, as my knees locked me upright on the escalator to ground level at my stop. What is it for? Our workshop sessions marked the best moments of my week—and the singular, empty feeling I had leaving the jail once they were over, marked the worst.

This year, Greg Kwedar’s Sing Sing, a new film about Sing Sing Correctional Facility’s Rehabilitation Through the Arts (RTA) program, reawakened this singular feeling in me, gently answering the existential question that arose from it. What is it for? The film tells the true story of artists Divine G, a playwright and RTA veteran who uses theatre to process his pain, and Divine Eye, the talented but cynical newest member of RTA’s theatre troupe who has trouble buying in, as they find meaning and confront demons in rehearsal and onstage. It features actors who are alums of the RTA program playing themselves, including stunning breakout star Clarence Maclin as Divine Eye. In telling the stories of artists creating amid the abject cruelty of prison, Sing Sing makes a compelling case for the humanity-affirming power of theatre, while laying bare its limitations. In this way, Sing Sing has much to tell theatremakers about our art form, if we listen. And we should.

Through its exquisite rendering of everyday moments of deep pain and hard-fought joy in prison, Sing Sing challenges oversimplified, self-congratulatory narratives about what theatre can do. Instead, it favors specificity about the fleeting but vital reprieve the art form can provide in the lives of people who are denied the full spectrum of their humanity. The film delicately holds the tension between the vulnerability and sanctity of the artistic process and the harsh realities of the law and its institutions as the container for this process. Most apparently, Sing Sing illustrates the practical ways that this container limits the act of making theatre. The program lacks funding, which has the cast making the best of cardboard pirate ships and towels for kings’ robes; they try to impress the superintendent with their stage combat skills in the hopes of acquiring enough cash for new curtains. Lockdowns prevent cast members from making it to rehearsal. While their bodies are their instruments, they ultimately have limited control over their own bodies. Such are the trials of theatremakers whose stage is inside a maximum security prison.

What does it mean to make art with people, knowing it won’t break open the cages that confine them?

These practical limitations are manifestations of something less tangible. The carceral system, which disappears people from society as a form of punishment, is fundamentally in conflict with the purpose of art, which is to deeply know ourselves and each other. (I’m paraphrasing the great James Baldwin’s “The Creative Process” here.) The film’s sharp focus on the characters’ rich inner lives is repeatedly shattered by reminders that the cruelty of the legal system structures their outer lives. This is the story’s rhythm. Moments of artistic and emotional discovery in rehearsal are punctuated by destructive cell searches, the constant threat of physical violence, and the hopelessness of failed clemency and parole applications. When juxtaposed with the legal system in this way, the philosophical limits inherent in the act of theatre are laid bare.

Watching Sing Sing, I was reminded of something I often take for granted: making theatre is doing something insofar as it is pretending to do something. Fundamentally, the doing is pretending. And pretending to do something is not the same as actually doing it. For example, staging a play about resistance to structural oppression is not inherently chipping away at the structures’ power over and material impact on people’s lives. This gets at the root of my post-poetry workshop existential dilemma: what does it mean to make art with people, knowing it won’t break open the cages that confine them?

The power of art does not matter in the context of the law—which is the only context in which these characters can fight to achieve their literal freedom. Toward the film’s end, Divine G attends his clemency hearing. Though his multiple appeals to his murder sentence over the years have been unsuccessful, he has a renewed sense of hope, having uncovered evidence that proves his innocence. The evidence is deemed unusable by the clemency board, and his application is ultimately denied, but not before the board asks him about the RTA program. After passionately explaining the program’s positive impact in the lives of its participants, hoping it might sway the board in his favor, they ask him only one question: “Are you acting in this hearing?” Crestfallen, he flounders, trying to explain that acting is not lying, but processing, moving through multiple truths. This moment is perhaps the story’s clearest example of the prison’s incompatibility with theatre. The carceral system is not built for empathy or understanding—just the opposite. How could it possibly recognize the power of art to transform people? Divine G’s artistry cannot convince the board of his human worth; somehow, his most profound gift is a strike against him. It unravels him, triggering a plummet into hopelessness.

Being free onstage is not being free in real life. Playing pretend does not change reality. In calling attention to that obvious but critical truth, Sing Sing challenges the artistic exceptionalism that characterizes so many stories about the power of theatre. In this context, theatre is not the embodiment of freedom. Freedom is. Theatre is not mercy. Mercy is. Theatre is not the realest, truest, or most just act. The characters in the film make theatre so they can “become human again,” as RTA member D-Dan (Sean Dino Johnson, playing himself) puts it. But it’s not cynical to say that that doesn’t change the fact that the outside world doesn’t treat them as such.

Importantly, amid all its real, hard truths, the film doesn’t begrudge its characters their human need for escapism. In fact, their cruel reality makes their need for escapism that much graver. There is no limit to what they can imagine, perhaps because without their freedom, imagination is all these theatremakers have. After all, they ultimately choose to stage a time travel-Western-zombie-horror-dance-comedy for their bi-annual production, for the expressed purpose of bringing laughter to the people in prison. It’s just that ultimately, it’s impossible for them to fully escape, let alone transcend the walls that confine them. After weeks “trusting the process” to realize this comedy, and years pouring himself into the RTA program, in a single moment, Divine G loses all will to keep creating. G’s best friend, Mike Mike (played by Sean San Jose), has died in his cell of a brain aneurysm. G has been denied clemency despite years of work to prove his innocence. He is tired of trying again. He ruins dress rehearsal by going on a mid-scene tirade instead of reciting his lines: “This bullshit we’re doing doesn’t really matter!” “We just do the same shit over and over again!” Trying to escape can be futile. In fact, for Divine G at this moment, it’s actively harmful. It only serves to distort the pervasiveness of his oppressive circumstances. It feels like lying. Narratives about the power of art often patronizingly suggest that it is possible to use art to “transcend” one’s circumstances. Sing Sing shows us just how reductive that is. Sometimes, we need to use art to momentarily escape violent, inhumane circumstances. Sometimes, as Divine G says in the film, we need to use it to “process” these circumstances, moving through them. Often, transcendence is too much to ask for. 

If theatre is not the embodiment of freedom in this context, it is one embodiment of hope. In its exploration of these imprisoned artists’ evolving relationships to their art, Sing Sing charts a human cycle of hope to hopelessness to hope again. The play is not the main thing, not ever. And yet, the characters always come back to it. Divine G ultimately does, even after his dress rehearsal transgression, and is welcomed with open arms. As he puts it, “This fucking program is all these motherfuckers got.” They apply for parole or clemency. They make plays. They get denied parole or clemency. They make plays. They apply again. They make plays. In this way, continuing to pour themselves into the theatremaking process is their active assertion that their lives have meaning. As the carceral system tries to convince them that they don’t matter, that is nothing short of momentous. In Sing Sing, making theatre is a hard-fought, disciplined choice to practice hope.

So surface-level narratives about the power of theatre to “heal all” don’t hold up in the abject cruelty of prison. Theatre does not heal the people in this story. It can’t possibly, and it’s patronizing for free artists to suggest that it could. In this way, the film humbles theatremakers about our artform, while showing us, with precision, the small, steadfast power it does hold. The strength of Sing Sing lies in its specificity about what theatre does for these people emotionally, moment to moment, as they need the dismantling of oppressive structures to materially better their life chances. It gives them a space in which to be kings and time travelers. It gives them a moment to imagine their “most perfect place,” a chance to do goofy exercises like walking around as though they’ve “won the lottery,” a song to dance to. It gives them a way to express their pain in an environment otherwise built on repression. A couple times a week, it allows them to embody the full expression of their humanity. That is meaning enough.

In Sing Sing, theatre is a humanity-affirming, hope-giving act. Watching the film, though, I was reminded that theatre is not inherently humanity-affirming or hope-giving. As with anything, it is a tool shaped by those who wield it, and how, and to what end, they do so. Often, theatre and its institutions reproduce the very oppression that structures the lives of the characters in Sing Sing. The recent, industry-wide reckoning with our racist practices and ideologies is evidence of that. Sing Sing illustrates that when theatre is wielded by those existing in opposition to the cruelty of the carceral system, its most profound impacts are more potent. If theatre is not healing the people in this story, they are, in a sense, healing theatre, by stripping it down to its core. The theatre in Sing Sing is focused, above all else, on the act of being human and creating space for others to be so. It is not focused on money, power, entertainment, or even craft. It is not hierarchical, but fundamentally collective (every decision is put to a group vote; every artist is a person first—with a set of unique experiences, emotions, and struggles that makes them a better artist). It is made in a space built not on ego or transaction, but mutual care. It is as much or more about process as it is about product (in fact, we never see a final performance, as the story ends instead on Divine G being released from prison). It is raw and unregulated. It exists without the sanitization of art-making institutions. And above all, it fundamentally resists structural oppression, by undermining the inhumanity of the prison system.

Free theatremakers must know the critical difference between the pathologizing endeavor of taking art into prison to impact the lives of imprisoned people, and honoring and nurturing imprisoned artists.

So the characters in Sing Sing are making theatre truer, righter, and more humane. This is summed up in a pre-show huddle up ahead of their culminating performance. After a beloved cast member has died and Divine G has given up and then returned to the show again, their director, Brent (Paul Raci) says, “Who would have thought that the beginning of the healing for this planet would start right here, behind the walls of Sing Sing?” They are not being healed but instead do the healing. Free theatremakers must know the critical difference between the pathologizing endeavor of taking art into prison to impact the lives of imprisoned people and honoring and nurturing imprisoned artists. Some of the greatest artists we have are locked up, contending with great barriers to sharing their art with the world. As much as they need to witness the art of the outside world, the outside world needs to witness theirs.

Empathy is widely referenced as the highest ethical charge of our work as theatremakers. Bill English, the co-founder and artistic director of San Francisco Playhouse says, “Theatre is like a gym for empathy.” Sing Sing shows us that profound things happen when the gym for empathy is run by people who are systematically deemed unworthy of it. It paints a detailed, messy picture of how theatre can activate and answer back to this human need for empathy—a need strongest in communities that are routinely denied it. Theatre is most true, most just, and most impactful when, often against the odds, it reaches these communities.

If we are to call theatre empathy in practice, and ourselves empathy practitioners, then it is our responsibility to contend with the strengths and limitations of our art form in the most abject circumstances our society produces. Confronting this can make our art less self-important, and more meaningful, grounded, and vulnerable. It helps us approach our work with humility, understanding that it’s not some untouchable salve for all wounds, but taking seriously its ability to provide a sense of hope amid all the darkness. And critically, it reminds us to position ourselves always in opposition to systems that threaten empathy and hope. Prison abolitionist Mariame Kaba says, “hope is a discipline.” Sing Sing crystallizes this sentiment, coloring it in. Hope is our ability to believe in a more humane world, with softer places for people like Divine G to land. Theatre programs like RTA nurture this ability, giving theatre its greatest impact.