This article appeared in the November 22, 2024 edition of The Film Comment Letter, our free weekly newsletter featuring original film criticism and writing. Sign up for the Letter here.

Songs from the Hole (Contessa Gayles, 2024)

My neighbor in Carroll Gardens, Brooklyn installs an elaborate Halloween display every October, with severed heads, killer clowns, vampire bats, and even a freshly dug grave. The centerpiece of these horrors is an orange jumpsuit–clad man in an electric chair that buzzes when plugged in at night. Families, mostly white and affluent, stop by with their children. Some pose for pictures. I often linger nearby, curious to know how parents explain the execution scene to their children. I once heard, “He did something very bad.” I wonder how many know that the first execution by electric chair happened in Auburn, New York in 1890, or that more people have been executed in Sing Sing—located a mere 45 miles from Brooklyn—than at any other American prison.

Prisons are often hidden, even to those near or around them. The village of Sing Sing changed its name to Ossining in 1901 to distance itself from the maximum-security prison, which stretches across the Hudson River waterfront. When I drove to Sing Sing on October 24 for the first-ever documentary film festival inside prison walls, Google Maps directed me to the decommissioned 1825 cellblock built from marble mined by incarcerated people (it will be reopened to the public in 2025, as part of the Sing Sing Prison Museum), rather than to the newer, massive cellblocks, where nearly 1,500 men are incarcerated today behind 24-foot-high walls. The remoteness of prisons and those they disappear makes it easy for people removed from the experience of incarceration to devise justifications for the deprivation of liberty. Criminologist Michelle Brown calls these practices of vicarious judgment “penal spectatorship.” If you think about it, penal spectatorship is quite pervasive and mundane. It has been normalized by a mediascape where screens are dominated by cop shows, legal dramas, and true-crime documentaries.

What can representations of mass incarceration tell us about its true function when the people whose stories they mine have so little control over them? For journalist Lawrence Bartley, who was formerly incarcerated at Sing Sing, organizing the film festival was about inserting the lived experience, expertise, and judgment of incarcerated people into film discourse. Bartley, who now produces reporting specifically for incarcerated audiences through the Marshall Project, explained to me that many purportedly factual representations of life inside are inaccurate or misleading: “I wanted incarcerated people to get a chance to be on a jury, and to learn—through engagement with a filmmaker we brought in—how to look at criminal-justice films critically. Who better than them to fact-check films?” Focused on criminal-justice documentaries, the Sing Sing Film Festival followed close on the heels of the San Quentin Film Festival, in which works made by incarcerated people, utilizing the resources of the San Quentin Media Center, dominated the nonfiction category. With no film program or media center at Sing Sing, demand for progressive programming far outstrips availability. The Rehabilitation Through the Arts theater program at the prison, made famous by the 2023 film Sing Sing (which features formerly incarcerated actors alongside star Colman Domingo), has a waiting list of over 100 applicants.

The festival was defined by the restrictions that prisons place on media access. Internet use is banned at Sing Sing, and incarcerated people pay extortionate rates to access most content on individual tablets. “You have to transfer $8.99 to purchase new releases, or $5.99 for older films, but you only have 48 hours to watch,” explained Noel “DJ” Rivera, who served on the incarcerated jury of the festival with four others: Raheem “Radio” Edwards, Michael Hoffler, Alonzo “Tiny” Miles, and Jonathan “Jay” Mills. (Hourly wages in New York State prisons average $0.62.) The tablets have “a few free things—for now,” including PBS and TNT, but “the video pool sucks,” according to Nigel Francis, who—along with Alexander Aguilar, Jean Gehy, Xiaobao He, and Anthony Wager—served as an alternate on the same jury. Films shown in prison must be cleared by licensing middleman Swank. The Department of Corrections adds a long list of content restrictions: no films featuring riots, sexual violence, the making of shanks, or anything with the potential to incite violence.

The most glaring effect of these restrictions was that the festival’s Competition lineup wasn’t actually screened at the festival. Marshall Project staff reviewed almost 40 films to arrive at five finalists and one alternate for approval by the DOC’s media-review team in Albany. But the finalists weren’t on Swank’s list. Per Bartley, a screening for five people or fewer can bypass Swank requirements, which was how the jurors were able to see the final slate—but there was no way for the rest of the incarcerated population at Sing Sing to watch them. The jurors received training in film criticism from documentary filmmaker El Sawyer, and discussed and rated the films with regard to character development, storyline, relevance, editing, and ethics. Rivera felt grateful for the skills he learned through this process: “It brought into scope how I watch,” he said, adding, “I learned how to pay attention to hidden messages.” Francis, who has two young daughters, was especially moved by Daughters, which received the festival’s runner-up prize, an “Honorable Mention,” for its life-affirming depiction of contact between incarcerated fathers and their daughters.

Staffing shortages meant that the festival was, as Marshall Project President Carroll Bogert put it, “not really a festival.” The New York State prison system faces a labor crisis, which led to the closure of two prisons earlier this year. Bartley’s team—which included his colleague Donald Washington, Jr., and a consultant, Kiki Dunston, both formerly incarcerated—was able to negotiate an afternoon-long event comprising an awards ceremony, a panel discussion, and a program of three short films shown with the consent of the filmmakers (Bao Nguyen’s Four Letters, Nadav Kurtz’s Sam and Omar, and Thanh Tran and Rahsaan Thomas’s San Quentin Media Center in a Box) and an excerpt from an episode of the Marshall Project’s Inside Story, directed by Washington. The more than 100 outside attendees could eat, drink, and mingle with approximately 30 incarcerated men (visitors I met included representatives of a major advertising agency, a company that provides learning platforms and tablets for use inside prisons, and funders and producers of social-justice documentaries). We barely filled half of the 500-person auditorium where we gathered after a stringent security process. The many forbidden items included phones, Bluetooth devices (one attendee had a Bluetooth-enabled breast pump requiring special clearance, as did the notebook and pen I asked to bring in), underwire bras, and, to avoid confusion with the incarcerated men’s uniforms, hunter-green pants.

A scene from Daughters depicts the painful impact of jails and prisons downsizing from in-person or “touch” visits to costly video calls with family members elsewhere in the same building. Festival visitors also experienced this diminishment of collective experience: as opposed to watching the contenders together, we were sent links on four different subscription-based streaming platforms in advance of the event. Being physically present at the festival, sharing food, and interacting with incarcerated men—some of whom, like Jonathan Jolivert, were watching a film in the auditorium for only the second time in three years (the first was when Sing Sing was screened there in June)—was a powerful experience. My highlight was introducing Francis to San Quentin Film Festival co-founder Rahsaan Thomas, who shared his path to filmmaking through the Prison Journalism Project, and recommended that Francis “get into writing.” Moments like this underscore the value of “access” in prisons not as securitized permission but as the hard, necessary work of enabling meaningful social participation. Indeed, a central theme in the festival’s curation was the need for transformative safety, created not by confinement but by community, revolutionary love, and collaboration—whether through the mutual support among mothers whose Black children have been killed by police (For Our Children), the advocacy of those struggling with reentry on behalf of those still inside (Commuted), or the freedom-work of Black music (As We Speak).

Why show—or make—films in prison? Commissioner Daniel Martuscello III, who determines the budget for New York State prisons, had a ready (if cynical) answer in his opening speech: “Progressive programs are good security.” Prison programs have a token role in the lives of people inside, especially after the 1994 Crime Bill, which decimated educational opportunities for incarcerated people—including ending Pell grants for almost 30 years—while bringing historic numbers of mostly Black, brown, poor, and disabled people into prisons. Asked about starting a media center at Sing Sing, Martuscello was quick to stress the need for more staff funding. When the winner of the Sing Sing Film Festival was announced—Songs from the Hole, a visual album structured around the work of incarcerated artist James “JJ’88” Jacobs—director Contessa Gayles had a different answer: “We made this film to imagine a future where places like this don’t exist.”

Five minutes later, we exited in two lines: one for the men in green pants, returning to confinement, and one for the visitors, leaving to freedom.

Pooja Rangan is a professor of English in film and media studies at Amherst College, and the author of Immediations: The Humanitarian Impulse in Documentary (Duke University Press, 2017) and The Documentary Audit: Listening and the Limits of Accountability (forthcoming from Columbia University Press, 2025).