OSCARS 2025: Sing Sing (2024)

Everyone loves an inspiring true story. In 1996, a group of inmates at Sing Sing Correctional Facility in New York approached minister Katherine Vockins about getting help putting on a play. This was the beginning of Rehabilitation Through the Arts, a program designed to bring art workshops to prisons. RTA is currently active in ten facilities around New York and seems to have contributed to low reoffending rates. It's a nice story and one that caught the eye of screenwriter Greg Kwedar, who made his directorial debut with "Sing Sing," a fictional film about the organization that used real graduates from the program. Now Kwedar and the film's star, Colman Domingo, are nominated for Oscars. 

Divine G is an inmate at Sing Sing, imprisoned for a crime he did not commit. G has become heavily involved with the prison's performing arts program, both writing and starring in the plays. New inmate Divine Eye grabs G's attention and he recruits him into the program. G wants the next play to be a drama but Eye suggests a comedy, which the other inmates are enthusiastic about. As the story takes shape, G and Eye bristle against each other until he convinces the new addition to open up a bit. While working on the play, G is also gathering evidence to clear his name. The dual stresses begin to weigh on Divine G, threatening both the performance and his chances of being paroled. 

If we agree that toxic masculinity is a real thing, I think few elements contribute to it more than men never being taught to process their own emotions. To this day, a lot of boys are told to suppress any feeling but anger. I have no doubt that this contributes to the rate of violent crime and other offenses. This is one of the central ideas of "Sing Sing." As Divine Eye joins the theater trope, he's confrontational at first and attempts to start fights over simple infractions. In a soft, intuitive way, G gets Eye to get in touch with his inner feelings and process how he interacts with them in a healthy way. In other words, it's a form of therapy that works without the participant necessarily noticing it. That's probably a good way to reach men hardened by their lot in life and the environment they're in. The proof is in the pudding, since Divine Eye – real name Clarence Maclin – and most of the supporting cast are genuine graduates of RTA, essentially playing themselves in the film.

There are other reasons why I think theater works as an effective form of therapy. Throughout "Sing Sing," we see the joy the men feel in being a part of creating something. The brainstorming session, where they toss around a bunch of crazy ideas for the play, is one of funnier moments in the film. Honestly, I think creative endeavors are both a good distraction from the daily strife of prison life and a good way to give these perhaps hopeless men something else to look forward to. It creates a sense of brotherhood among the guys, collaborating with one another and appreciating each other's talents. This is true in both real life and the film. The scenes devoted to the inmates putting the play together, assembling a seemingly random set of ingredients into some sort of coherent story, are a delight. Sometimes you seeing all the puzzle pieces fall into place, through colorful montages and opening night jitters, is entertaining enough. (Especially when those ingredients include time travel, ancient Egypt, and Freddy Krueger, making me wonder how many times that particular character has been mentioned in an Academy Award nominated film.) 

Honestly, the parts of the film focused on the theater trope preparing their play prove a lot more natural than the other subplots. G's attempts to clear his name and be successfully released never feel like a natural inclusion to the plot. These scenes often seem to exist specifically to provide those Oscar clip moments. Such as a tearful presentation for the parole board or, especially, an outburst of anger during a rehearsal. The pressure to make "Sing Sing" function more like a traditional drama is also apparent in a sudden plot point midway through, which never feels organically included and comes out of nowhere. (Intentionally but still.) Considering he's an experienced screenwriter, it's a bit surprising that Kwedar doesn't seem to trust the value of the already existing true story, ironically counteracting the repeated line of "Trust the process." If "Sing Sing" was simply a film about a group of prison inmates putting on a play, it would be just as good as it is now and probably better. 

Not to say that the film is bad. Cinematographer Pat Scola has a good eye, combining more naturalistic moves with some expressive colors. Colman Domingo, unsurprisingly, is excellent in the lead. Domingo has a screen presence that is both easygoing and accessible, put to good use as a guy trying to get other men to open up a bit, while also being able to put some real muscle into the more dramatic moments. As filled with showy speeches as "Sing Sing" might be, they are all well done. Clarence Maclin is also very good, seeming fittingly unrefined in a lot of ways while showing a fine sensitivity as an actor. All of the guys are clearly comfortable on-camera, bringing a lived-in camaraderie with each other to the group scenes. All of this suggest that a more straight-ahead true story about the Rehabilitation Through the Arts organization might have made for a better formed film, rather than squeezing those details into a traditional drama. 

If "Sing Sing" ultimately can't rise above the label of being Oscar Bait, it still is a good film. Domingo's carefully considered abilities and fiery passion make for a dynamite lead while the supporting cast obviously brings a deeply personal, unique approach to the behavior. I'm predisposed to enjoy any story of a rag-tag group of misfits coming together to put on a show, a formula which "Sing Sing" happily embraces in its best moments. Despite aiming directly for the hearts of Academy voters at times, this still functions as a largely understated and sweet story about forgiving the self and redeeming the soul through the medium of the arts. Maybe it should've have been a documentary. Hopefully, Kwedar takes his own advice and trusts the process more on his next feature. I also hope to see some more of Maclin and the other actors in the future. May this film be the beginning of their own stories of expression and artistic fulfilment. [7/10]