Sing Sing: Art Power's to Resurrect isn't Enough

It's better than Rustin, hooray!

Starring Colman Domingo and inmates from the real-life RTA program at the Sing Sing correctional facility, debut filmmaker Greg Kwedar, and writer Clint Bentley combine documentary elements with a sentimental core to chart the quest of these inmates to connect to their common humanity through art. Picked up by A24 during last year’s TIFF Festival, Sing Sing was silently dropped in the summer months, finally reaching more theaters in its wide release. Attaining rave reviews at the festival and growing into a serious Oscar contender in the coming months, does Sing Sing live up to the critical acclaim?

Based on the real-life rehabilitation program captured by Brent Buell’s novel The Sing Sing Follies, Colman Domingo stars as John “Divine G” Whitfield, an inmate who is wrongfully incarcerated for a murder he allegedly didn’t commit as a small-time drug dealer in the 80s. Serving life in prison, Domingo finds ways to distract himself from the isolation by reading up on the law for future parole hearings, convinced a recently discovered videotape will exonerate him. However, he mainly focuses his energy on the RTA program where he writes and acts in plays with the other inmates to help them heal and get closer to their emotions. A fellow inmate Clarence “Divine Eye” Maclin, incarcerated for gang-related violence, is reluctant to join the group, afraid of performing despite his artistic inclinations. However, John welcomes him in as he learns to break out of his self-defeating cycle of violence and toxic masculinity to become a better person through art. All of these personal dynamics play out while the group attempts to put on a comedic production that’s a hodge-podge of several different genres to cheer up the inmates. Juggling the play, his efforts to reduce his sentence, and welcoming in a new member to RTA, Domingo’s Divine G finds himself fighting against several things. 

I think it’s wonderful to see a film that tackles incarceration. There have been plenty of documentaries that highlight the struggle behind bars, but rarely do narrative films do that. Many countries fail to do right by incarcerated individuals, especially America. People in the country, from our politicians down, seem to have an almost Old-Testament view of justice, rarely considering the human potential to change or redeem oneself. Sing Sing aims to explore this very virtue of the human condition. It’s high time for films to take a deeper dive into the prison system in America and elsewhere. As opposed to other prison dramas which prioritize grit and grime, the film takes a realistic look at the redemptive power of art and the quest to choose hope over cynicism. With an ambitious subject matter, Sing Sing saves most of its room for the performances. Each character is expertly drawn out, with many of the real-life members of the program playing themselves. It is however Domingo’s performance that shines the most. I’ve enjoyed seeing his rise to prominence in the past two years, paving his way as one of the best actors in the industry. Prioritizing subtlety over bravado, Domingo manages to express so much with so little where a little glance or change in expression could fill up a page. Although, the performances are wonderful all around which is a testament to Kwedar’s direction. The non-actors appear at ease and adept at screen-acting, ushered in by a director who knows how to work with them. Charting the capacity for individuals to change and how important the little things are in life, Sing Sing’s goals are ambitious yet have room for more. 

While I appreciated the way Kwedar shows how toxic or at least exaggerated masculinity amongst black communities prohibits any true feeling, many of the larger socio-political criticisms either fall flat or aren’t given enough energy. Certainly, the film spends more time focusing on the inmate’s turmoils, but certain missed opportunities could have lent the film greater gravity. The entire film stays restricted to this one RTA program, rarely looking at life outside this haven. There are a few monologues and moments (parole hearings, especially) where you empathize with these characters' struggles, but the filmmakers rely too heavily on performances to achieve this. What truly holds Sing Sing back is the lack of a clear voice behind the camera. Kwedar and Bentley are surely well-intentioned in handling such an important and ambitious subject, but do either of these men have any special connection to the material? Granted, I don’t know their entire life histories but I’ll lean towards these two white men not having a deep personal understanding of these characters. I’m not saying that you have to be an inner-city black man to portray the lives of these characters but that the filmmakers need to have an active role in the storytelling with something unique to say. Frankly, a mockumentary version of Sing Sing could have appealed to their filmmaking sensibilities. Regardless, in the existing film, I never felt the filmmakers’ personal imprint on this film whatsoever. I’d be hard-pressed to find ways to distinguish Sing Sing from the countless indie films released in the past ten years. Thus, there’s a certain amount of detachment to the project that only allows it to function as a nice, feel-good true story film instead of the serious statement it could have been. 

While it sounds like I’m coming hard on Sing Sing, for a debut film, it’s largely effective. The subject matter and performances may be impressive but the film fails to live up to its lofty promise. Still, the film is a pleasant and sensitive prison drama about the ability of people to resurrect themselves through art with an anything-is-possible kind of attitude. Sing Sing may not be a great film, but it’s a very good one. However, concerning the Oscars, I’m hard-pressed to see how outside of Domingo, Sing Sing can come close to Oscar glory. [3.25/4]