If you type “Sing Sing” (2024) into IMDb, “Sing 2” (2021) appears before the movie set in the New York State maximum security prison, Sing Sing Correctional Facility. This adaptation of John H. Richardson’s Esquire article, “The Sing Sing Follies,” published on October 1, 2005, stars Oscar nominated, best dressed and most handsome living male actor Colman Domingo as John “Divine G” Whitfield, a prisoner and cofounder of Rehabilitation Through the Arts. Every six months, the program’s members put on a theatrical stage show. After finishing Shakespeare’s “A Midsummer Night’s Dream,” the group is ready to admit new members and select their next play. Despite others’ doubts, including his best friend, Mike Mike (Sean San Jose), Divine G vouches for a new player, drug dealer Clarence “Divine Eye” Maclin, who plays himself. Over the course of the next six months, Divine G and Divine Eye challenge each other and find themselves at a crossroads of choosing to rediscover their humanity and feel pain or numb themselves by playing the role of the hopeless prisoner.  Will they ever be free?
Director Greg Kwedar’s sophomore feature film introduces Divine G at the height of his game: on stage performing as a king. The twist is that stage is not on Broadway, but in a prison, and Divine G is not a union card carrying actor, but a prisoner. It strains the suspension of disbelief that anyone could see such a majestic man and be wary of him. He is convincing as a king and an artist because Domingo is playing him. It is not a heavy lift especially because even when playing disreputable characters, Domingo has a commanding, charismatic air as if his victims are still fortunate to have the privilege of becoming his prey. In this performance, there is not a hint of anything but respectability. Even without knowing the details of how Divine G ended up in this predicament, it is credible that he is innocent and wrongfully convicted. Now he just needs to convince the penal system’s bureaucracy. 
Our universal admiration for Domingo not only translates into respect and the benefit of the doubt for his character, but also the men that Divine G regularly socializes and collaborates with, even the ones that he roots for who seem a skosh less credible like Divine Eye. 
Even though he applied for admission into the program, Divine Eye acts as if Divine G and the troupe have a hidden, violent, perhaps sexually nefarious agenda though there is no objective evidence supporting his wariness. On the contrary, he is the one who seems like a danger to the civilians who support the program by explicitly expressing his interest in the production volunteers, who are women. He starts off as a possible threat to the program as if he is only out for himself, reacts aggressively to the troupe, refuses to participate in acting exercises, and acts on his desire to pursue a romantic relationship with volunteers. To anyone except Divine G, Divine Eye seems like a bad bet. Gradually Divine Eye melts and only poses a threat to Divine G’s place in the troupe as the lead actor and pacemaker in setting the direction for the season.
While each member of the troupe gets to share a sliver of the spotlight, other than Mike Mike, none are as individuated as the Divine moniker men with Divine G as the true protagonist. Kweder’s camera often shows Divine G’s perspective, so it becomes obvious that Divine G feels a seed of resentment and insecurity at Divine Eye’s redemption arc, especially since he does not entirely fit the formula of one deserving a second chance. Divine Eye sees Divine G as an equal, not someone to admire, and while Divine G does not want followers per se, in this small pond, he is not used to being anything but the lead artist who determines the direction of the play, his place in it and the role that each member plays. Certain rules govern Divine G’s world, and when those rules do not deliver a predictable result, i.e. good things happening to good people, and he begins to be stripped of everything because of random circumstance, Divine G experiences a crisis of faith in the system and the arts.
“Sing Sing” is not just about the redemption and resurrection of the spirit of men that society wrote off but is about not taking for granted that once saved, always saved. Divine G, the most secure and perfect inmate, is in danger of losing himself and falling through the cracks of the system. What is the point of being the best if there is no reward for it and one is still punished? It is a universally relatable situation for all the strivers who feel unrewarded and are wronged yet required to continue to carry the burden of a respectable person to still hold on to the possibility of emerging at the other side.
If possible, try to watch “We Grown Now” (2024) before “Sing Sing.” In both films, Black characters are visually depicted as transcending their oppressive surroundings and living lives of joy in all circumstances, which is difficult work when everyone else is trying to create a way of life that instills fear and stamps out individual humanity. One image shared in both films is looking out at the horizon, whether an inspiring city skyline or awe-inspiring nature through bars or chain links and being able to erase those barriers and imagine yourself out in the world. The lesson of both films is to not do the systemic work for them, and the antidote is play, imagination and relationships. While Divine Eye is a destabilizing presence in Divine G’s life, he is also a potential lifeline. In an environment as innately isolating as a prison, no one can have too many friends, which also explains why the acting program is such a balm to the soul. It continues that vision of being outside by being able to play pretend, wear civilian clothes, not get guarded or perceived as a prisoner, but as someone else. Theater director Brent Buell (Paul Raci, who resembles an American brand Richard E. Grant) treats them as the professionals that they are, not people to fear or be suspicious of. 
While “Sing Sing” can be predictable in the overall trajectory of the narrative, it does avoid certain cliches in the relationship between the Divine men. The threat of a battle for ascendency never happens, and it is a relief; however as one character offers more details about his past and expresses regrets, you can set a watch to his certain demise. Also the eventual parole board appearance goes as expected as does the denouement. It is the kind of movie that feels as if it would make a better documentary, and after investigating rumors that one existed, not a single work fit the bill (please write in if you find one) though some videos show a fraction of the scope of the film. This film may feel as if it falls a little short, and there is still room for improvement, particularly in exploring the stories of more of the alum and not trying to fit their lives into familiar tropes already covered in fictional films like “The Shawshank Redemption” (1994). Fortunately, it does avoid the most horrifying tropes of rampant violence, including sexual violence and gang warfare.
“Sing Sing” can be a difficult movie to watch because it is tiresome that there are still true-life stories of systemic injustice that people must overcome. Why is the burden of humanization placed on the shoulders of individuals and nonprofits instead of the justice system? There are two theaters, which includes the theater of justice. Off-screen, prior to the beginning of this movie, in court, and a later, on screen scene when Divine G appears before the parole board. This audience finds him less convincing as himself. His accomplishments as a talented actor becomes an accusation that he must defend against as if he is lying to them. (Side note: the most insensitive parole board member wears the nicest suit.)
If you see “Sing Sing,” stay until the end to find out which actors are playing themselves and which are playing a fictional role. It will make the film retroactively more impressive, especially considering that many films where people play themselves are often unwatchable such as “The 15:17 to Paris” (2018). This film is proof that these men are such serious and excellent actors that they have made a standout movie and were able to work with a living legend like Domingo.