The Hidden Beauty Within the Dark and Sinister Sing Sing

17th Dallas International Film Festival

By Brian Landa
@BrianLandaLawyer

Ossining Correctional Facility, New York State – Known by the nickname “Sing Sing” for generations. Now it’s official. Sing Sing Correctional Facility. The name sounds a bit silly, but silly it is not. The very name conjures dark sinister images of Vincent Price in The House of Wax (1953) and Old Sparky-style electric chairs. And John Waters strategically screening his earliest celluloid atrocities there for a more than captive audience.

Now, due to a potentially life-altering eponymously-named film demonstrating the importance of impactful art on the inside, and impactful as a work of art in and of itself, Sing Sing also conjures images of wacky costumes. And improvised theater. And men who are able to feel human again. 

On the legendary television series Mad Men, one of the characters lived in the pastoral beauty of Ossining along The Hudson River, with nary a mention of the prison, historically one of the most notorious prisons on earth. Its reputation is worse than its reality perhaps. The present reality anyways.

The movie Sing Sing, which is one of the buzziest films of recent memory (but with no solid national release date as of yet) has been a hot ticket since Toronto, Sundance and SXSW. I finally got the chance to see it at the Dallas International Film Festival 2024, with the filmmakers in attendance, including director Greg Kwedar, who co-wrote the script with Clint Bentley (such as it is – lots of improvisation here, which is why it feels real and immediate). I had no idea there was local involvement, but Kwedar is based in the Dallas-Fort Worth area.


The film is a hybrid reality/fiction story set specifically at Sing Sing, in the world of rehabilitative theater programs for incarcerated prisoners, specifically the actual Rehabilitation Through the Arts (RTA) program at Sing Sing. Some participants have zero chance of parole. Many others deal with ongoing parole hearings, including our “hero” Divine G, as portrayed by Colman Domingo (Euphoria, The Color Purple 2023, American Fiction).

The way this film came to be is amazing in itself, because it started out as the filmmakers independently volunteered to be part of the art programs inside. They saw this particular RTA program in action and decided to make a movie about it, using both Hollywood actors and several former Sing Sing inmates who participated in the actual program and were willing to be part of the film.

I will refrain from listing other performer names here, as figuring out who is a real ex-con and who is an actor is part of the enjoyment of watching this one, because at times it can get pretty rough. It is a prison film, after all. Some of the play within a movie material (scripts and costuming) is directly from the actual productions, and it’s fun to see the recreations. Some actual footage of RTA productions also accompanies the end credits scroll.

The Academy of Motion Picture Arts & Sciences may as well engrave Domingo’s Oscar now, because the emotions and the passion that Domingo put into this role are above and beyond. It’s a subtle performance, with rare but stunning explosive moments. Earned and deserved. If Nomadland, which is also a reality hybrid, can win Best Picture and another Oscar for Frances McDormand, Domingo can certainly win Best Actor. And should.
There are some very abrupt artistic choices, but I think that’s by design, and in service of making the viewer feel the helplessness of the people inside. They may be rehearsing and dancing and singing and having fun, but they are still incarcerated. And along with the more silly “drama” – tensions do rise, both in service and in detriment to the creativity.

And many inside did indeed commit the crimes they are in for. But that doesn’t mean they should completely lose their own humanity. Divine G struggles to keep his. A playwright by trade, and possibly wrongfully incarcerated, much of the dramatic heft of the film surrounds Divine G’s attempts at parole, with scenes of research and hearings and the like.

And incredibly human this movie is. Joyous and shocking in equal measure. One beloved character disappears with such suddenness, that it’s almost difficult to wrap emotions around it. The filmmakers can’t truly make us feel like it is inside, but that is a very successful attempt. I still miss that guy.

Because Sing Sing as a facility is still very much operational, interiors were filmed at a defunct prison complex nearby, and the filmmakers had a single day to shoot exteriors at the actual Ossining prison location. Such isolation contrasts with such natural beauty. It’s a conundrum.

But these men find a way to find the beauty within as well. The show that is produced within the film allows for creativity and improvisation and participation. Outside volunteers come to assist with the production as crew and performers. The inmates that get to see the show see the benefits as well.

Rehabilitation versus punishment is a true key to prison reform. And this film is sure to spark real dialogue about all of it. Along with hopefully getting Domingo a taste of Oscar gold. Sing Sing is set for release July 12 in theaters nationwide.

15th Dallas International Film Festival