‘Sing Sing’ review: Colman Domingo delivers in prison-set friendship drama

Spiritually and visually luminous, Greg Kwedar’s Sing Sing is one of the year’s most powerful works. The movie follows a theater production at a New York prison arts program, and is for all intents and purposes a dramatization — but it remains so closely tethered to reality that it may as well be docufiction. Rustin Academy Award-nominee Colman Domingo leads an impeccable cast, many of whom were formerly incarcerated and play versions of themselves, in a tale of learning to “trust the process” of performing.

The film is an aesthetically alluring, emotionally rigorous look at the way men are molded — and broken — by punitive systems. Yet, at its core, Sing Sing is about finding hope and catharsis through creation, and the difficulties therein. Kwedar’s deft direction works in tandem with fine-tuned drama to craft naturalistic mosaics, drawn from a patchwork of real prison experiences, resulting in a work of community storytelling both in front of and behind the camera. 

That its cast and crew were all paid the same rate across the board, and given a share of the profit, isn’t just a necessary equity model — Hollywood at large, take note — but an embodiment of the movie’s collective spirit, which radiates off its canvas in every scene.

What is Sing Sing about?

Clarence Maclin and Colman Domingo in “Sing Sing.”
Credit: Dominic Leon / A24

Shot in a number of real penitentiaries — including Sing Sing Correctional Facility, a maximum security prison in upstate New York — the film is inspired by the true story of  an unlikely friendship that was perhaps destined to be. Domingo plays John “Divine G” Whitfield, an author/playwright incarcerated at Sing Sing, who takes a keen interest in the prison’s RTA program (Rehabilitation Through the Arts), which stages a new theater production every season. Meanwhile, Clarence “Divine Eye” Maclin plays himself: a drug dealer and prison yard extortionist who is reluctantly roped into Whitfield’s program. That the two men have similar nicknames is about where commonalities end.

Though the film pulls from real experiences, Sing Sing takes dramatic liberties in order to inject the story with intention and propulsive drama. Whitfield sees something in Maclin that perhaps he doesn’t see in himself, whether talent or the need (and potential) for rehabilitation. Whitfield has seen and experienced the RTA’s positive effects up close, but Maclin’s closed-off, hyper-masculine approach to emotional expression — which one can intuit as a survival mechanism in a world that shows unjust cruelty toward Black men — proves a hurdle to his participation.

However, Maclin reaches a turning point when the group gives him the floor and actually listens to his advice. He suggests a comedic approach for the RTA’s next production, rather than their usual fodder of Shakespearean tragedy or one of Whitfield’s straightforward dramas. Soon, the whole group has their input heard, and a riotous mix of Hamlet, ancient Egypt, and A Nightmare on Elm Street becomes a brazen time travel musical titled Breakin’ the Mummy’s Code — a real play once staged at the RTA, which Kwedar discovered in the 2005 Esquire article The Sing Sing Follies.

The path to staging Breakin’ the Mummy’s Code is winding, between attempts to garner more prison funding for elaborate sets and costumes to simply easing the tensions arising from Maclin’s involvement in an otherwise well-oiled unit. He’s confrontational, to the point of rejecting Whitfield’s help in both his performance and his upcoming appeal for parole. The enthusiastic author isn’t about to give up on him so easily. However, when Whitfield himself struggles with hopelessness and ire, it’s Maclin who uses the emotional tools he’s learned at the RTA to come to his friend’s rescue.

In centering its characters’ humanity through the lens of performance, Sing Sing becomes one of the best modern films about acting as well.

Colman Domingo and Clarence Maclin deliver tremendous performances in Sing Sing.

Clarence Maclin in “Sing Sing.”
Credit: Dominic Leon / A24

For the most part, Sing Sing’s ensemble blends into the movie’s naturalistic fabric, but the dynamic between Domingo and Maclin isn’t so seamless — albeit with good reason. Domingo brings a rehearsed, boisterous, theatrical quality to Whitfield, befitting of a seasoned stage performer who takes a special interest in shaping the RTA. Which is to say: He’s distinctly Domingo, with all the pronounced inflections, buttery-smooth delivery, and penchant for melodrama that makes his performances so worthwhile.

Whitfield’s resilience, and his belief that he’ll successfully appeal his conviction, make for vital dramatic centerpieces that inform Domingo’s approach. He’s so jovial and conversational that he never feels at odds with the film, but he does feel like an outsider — an erudite who displays hints of arrogance as he takes control of rehearsal sessions — which makes things all the more difficult for him when he begins to lose hope. Domingo, like Whitfield, has Shakespeare on his mind when he nears the end of his rope, becoming emotionally shattered in mind, body, and soul while projecting for the back row.

This makes for an intriguing dramatic contrast with the more naturalistic Maclin, and creates a wider chasm between them, which they need to work even harder to overcome. Maclin carries himself with a street-smart self-assuredness that frequently gives way to a deep sensitivity and pain — which Whitfield encourages him to access in their rehearsal sessions. Watching both actors perform, with different modes and methods but striving toward a common emotional goal, is a moving meta-text, and Sing Sing invites this reading through its numerous scenes of introspective acting exercises, allowing each participant to access their most walled-off emotions.

The RTA’s purpose isn’t just playtime, but rehabilitation of a kind entirely separate from the cruelty of prisons. Where punitive lockup and invasive searches don’t do the characters much good, their creative outlets afford them the chance to get in touch with their emotions in ways even those in the outside world might not. The film, in this regard, mirrors the harrowing and incisive 2017 film The Work, a powerful prison documentary whose group therapy sessions are strikingly akin to the emotional recall exercises of Russian theatrician Konstantin Stanislavski, whose acting “system” was a precursor to Lee Strasberg’s modern “method acting.” The more the characters in Sing Sing rehearse, the closer they get not just to their immediate physical goal of putting on a great comedic performance, but to the spiritual goal of finding their most authentic selves.

The movie’s ensemble captures this journey in thoughtful fashion. The central relationship between Whitfield and Maclin may be key to the unfolding drama, but let it not go unsaid: The performances are incredible across the board.

Sing Sing’s supporting players shine. 

David “Dap” Giraudy, Sean San José, and Colman Domingo in “Sing Sing.”
Credit: A24

The two other actors who join Domingo from outside the prison system are Paul Raci as Breakin’ the Mummy’s Code writer and RTA director Brent Buell, and Sean San José as Whitfield’s close friend “Mike Mike,” a Latino man whose “Hare Krishna” appearance — rosary beads, along with a bald head and shikha ponytail — hint at a turn towards ISKCON Hinduism for comfort. However, both Raci and San José come from a place of empathetic involvement with the prison system too. Raci, who appeared in Sound of Metal, is a CODA (a Child of Deaf Adults) and works as a sign language interpreter within the criminal justice system, while San José has worked with numerous theater workshops in Bay Area prisons and county jails.

Both actors bring a sense of fun, conversational naturalism that matches the rest of the cast, who largely play themselves, and draw from their experiences as RTA performers. Sean “Dino” Johnson has a tranquil presence, and his repetitive rehearsal techniques in the corner of numerous frames are sure to catch your eye; Jon-Adrian “JJ” Velazquez brings a reserved toughness that hides a subtle but recognizable vulnerability; David “Dap” Giraudy shines with a youthful energy that’s magnetic and tragic in equal measure (he should be at the club); practically every supporting actor has a story to tell and a face so interesting that their silent close-ups are usually enough to tell it.

In this way, Sing Sing is a beautiful, multifaceted movie that not only draws from the real lives of its ensemble, but centers each of their stories and personalities with a commitment to realism, which Kwedar and cinematographer Pat Scola ensure in immensely thoughtful ways.

Sing Sing is a gorgeously crafted drama.

Colman Domingo in “Sing Sing.”
Credit: Dominic Leon / A24

Sing Sing, for the most part, avoids the question of what these men did in order to end up behind bars. This only comes up for specific, plot-centric reasons concerning Whitfield and Maclin. Otherwise, the movie allows us to get to know each man through their jokes, their rehearsal techniques, their idiosyncrasies, and their deepest fears and fantasies when it comes to life outside the prison’s walls, as relayed through various thoughtful acting exercises. We get to know them as people first and foremost, and as artists rather than as “criminals” as determined by the state.

Like Breakin’ the Mummy’s Code — a combination of theatrical and cinematic influences — the direction in Sing Sing combines elements of the stage and screen to create something wholly unique. Its opening images, plucked out of time, feature Whitfield performing a Shakespeare piece in order to set the mood. The combination of this show’s blinding stage lights and the celluloid film stock create a dreamlike haze, with visual grain practically coming alive as it darts across the screen.

The movie also features a sense of stage-like blocking; the actors’ posture and body language speak as loudly as their voices, in moments of both camaraderie and conflict. However, as the camera captures these interpersonal dynamics, the cinematography takes a loose, freeform approach — a documentarian, cinéma verité aesthetic — playing with shifting focus in order to reveal new layers to each relationship.

Following an argument between Maclin and Whitfield, a two-shot of the would-be friends in profile captures their proximity, as the camera keeps a distracted Whitfield out of focus while centering Maclin’s silent remorse. It’s as though his attempts to reconcile were being blocked by the film itself, conveying the underlying emotions more powerfully than dialogue possibly could. Sing Sing never slows down, but Scola’s camera lingers just long enough on these silent moments in between conversations to be able to capture the words that go unspoken by men unwilling — or unable — to speak them.

Kwedar and Scola’s use of 16mm film creates a sense of timelessness. Through its visual language, and its production and costume design — limited to what’s seen inside the prison walls — Sing Sing feels evergreen, as though it could’ve been made, or set, in practically any decade. The movie also obscures the passage of time in disorienting ways, an effect of living behind harsh walls and razor wire fences.

However, the use of film also creates a vibrant visual contrast that feels vital to the movie’s underlying themes. The prison’s walls may be drab, but their cream and beige pillars are interrupted by light that doesn’t just stream through narrow windows, but wraps its way around them. The filmmakers lean into the natural texture of celluloid — particularly, the halation effects of Kodak 7207 film stock — to create an ethereal glow emanating from the outside world.

The men of the RTA, who mostly joke around with each other and try to get along, have to hold on to hope in some fashion. This usually takes the form of thoughts, stories, and fantasies of their lives outside the prison’s walls, which we never see, but which the cast narrates with longing and determination as they meditate during recall exercises. This affords them a sense of infinite emotional possibility, despite their physical confines. 

Despite the movie’s documentarian feel, and its self-reflexive approach to performance, Sing Sing is first and foremost an entertaining, engaging story of a community thrown together under oppressive circumstances. As much as it resembles The Work, it also echoes the rousing classical drama of Miloš Forman’s One Flew Over the Cuckoo’s Nest — only its Nurse Ratched is the ever-present specter of the American prison system, which seeks to stifle hope and personal growth.

For the men of Sing Sing, art becomes both refuge and rebellion, presented not only as a coping mechanism for incarceration, but a therapeutic alternative. Kwedar, through his gentle visual approach, affords each imprisoned character (and formerly imprisoned actor) the room — and just as importantly, the time — to tell their own stories, in ways that cinema seldom does. The result is a heartrending, visually enrapturing balm for the soul.

Sing Sing is now available to purchase on Prime Video.

UPDATE: Jan. 29, 2025, 2:45 p.m. EST “Sing Sing” was reviewed out of its U.S. premiere at SXSW 2024; this review was first published on March 27, 2024. This article has been updated to include information about the film’s streaming options.