Sing Sing (2023)

Rated R entirely for language.  There were times that we were wondering if the movie was PG or PG-13 because there wasn't that much offensive stuff in it.  Then someone would just curse up a storm and then we remembered that the movie took place in a prison.  But there's no violence.  There's references to violence that took place before the events of the film, but nothing on screen.  

DIRECTOR:  Greg Kwedar

Oh my goodness, if I can get this blog knocked out in the next 35 minutes, I will have been the most productive human being that ever existed.  No matter how long I make my "To Do" list, there's always just enough time to get the whole thing done with maybe a minute to spare in either direction.  I don't know how it works, but I seriously pushed myself really hard to get caught up with life as a whole.  And the crazy thing is?  I needed to do very little of it.  (NONE OF MY TIME WAS WASTED AND YOU DON'T GET TO TELL ME OTHERWISE.)

Is there such a thing as "too inspirational"?  It's a weird take to have, especially considering the slate of Academy Award nominated movies that 2025 has given us.  I've been writing so much about each and every Academy Award nominee and they've mostly been bummer movies.   On top of that, many of these bummer movies haven't been all that great.  I'm not talking about all of them.  I'm talking about more than usual.  But then we get Sing Sing, which might be pushing too much in the other direction.  Maybe all of the other Academy Award nominees pushed me too hard in one direction that I needed a bit of a middle-of-the-road movie.  But sweet Christmas, how do you give me a movie about convicts putting out plays and finding a brotherhood in that theatre troupe and expect me to take it seriously.

Now, "Based on a True Story" movies often leave me cold, mostly because the movie is probably far removed from what actually happened.  This movie is almost an experiment of cinema more than it is a play on what is reality.  Don't get me wrong: there's a lot of stuff going on here that feel heightened for the sake of storytelling.  After all, there was a documentary about this exact program in Sing Sing that probably does a more accurate job telling the stories of these actors.  But because Sing Sing needed to be a movie, there had to be liberties made.  But out of all the Based on a True Story movies I've seen, this one has to have a special place because the actors are playing versions of themselves. 

This made for an interesting debate between me and my wife.  A lot of the movie was us shouting that someone was a professional actor or if they were playing themselves.  It's pretty recognizable.  But there's a fabulous choice going on between Colman Domingo and Divine Eye.  Now, from what I understand, Divine G is in the movie playing another part.  (What is that like?  Colman Domingo is this intense actor who is the lead of this movie and your story is being played by this guy when you yourself are an actor?  The mind races!)  I don't mean to be rude at all.  The story is inspirational and these guys do a heck of a job for the movie.  But there's a bit of a gulf between what Divine Eye is doing and what the other guys are doing in the movie.  What are the odds that the story that they came up with between Divine G and Divine Eye would need to have Divine Eye be so good that he could hold his own to Colman Domingo?

That might be the biggest yellow flag for me in terms of verisimilitude.  Those two guys are powerhouses when it comes to performances.  I love it a lot.  But some of those story choices seem a bit artificial.  If anything, that's my major frustration with the movie as a whole.  With a documentary, the story of these actors putting on a quality show in spite of being inmates is more about reactions.  I'm sure that the documentary probably talked about the captivity of the soul and how against incredible odds, these guys put together that brought people joy.  It talked about the value of the arts to soothe the savage beast.  But that's not a narrative in any sense.  And I'm sure that there was fighting similar to what we saw in Sing Sing as a whole.  But the actual story is a little bit weak.  

Maybe it is because we've seen the prison story before.  I love Divine G as a character.  He's a bit pretentious, but I like that as a writer.  He's got this very specific celebrity within this prison.  In the world of Sing Sing, he's a published author.  Nowhere else is that true.  And he's got fans!  That's fantastic. But everything else has elements of The Shawshank Redemption to it.  Like, the parole hearing is just like every parole hearing we've ever seen in cinema.  There's someone who is speaking over the inmate, who is desperately trying to plead his case.  The conflict between Divine G and Divine Eye is one between the noble inmate and the thug.  And that's where the movie kind of suffers. 

Both Divine G and Divine Eye are dynamic characters.  Divine G is a character rooted in calm.  He is convinced of his own innocence and he believes in the system.  He understands the intellectual and spiritual value of having a rehabilitative theatre program.  But that foundation is shook when he loses his parole hearing.  I get that.  We get an adequate look at what makes Divine G tick.  It all makes sense when he starts finding himself through the program and with his brothers.  I like all that. But Divine Eye is the secondary protagonist.  He comes in as the stereotype.  He goes through the program, much like Randall Patrick McMurphy in One Flew Over the Cuckoo's Nest as a means to dodge the world of the prison.  And, no surprise, he becomes one of the most important parts of the project.  He embraces his failures to become the best Hamlet they've seen (although we don't have much context and the soliloquy ends at "Aye--there's the rub!").  

But we never have those growing pains moments.  We have a time when we have Divine G talk to him.  But even Divine Eye calls him out on this moment, claiming that this isn't going to change him and that's the stuff of movies.  So what made this hardened criminal who was using the system for his own comfort, come to understand that they were doing something noble and good up on that stage?  Instead, the movie just takes a shortcut and makes Divine G and Divine Eye best of friends.  I wanted to have the labor pains that this movie refused to give me.  If anything, a lot of the conflict in this movie is mostly "get over yourself" conflict.  There's no real come-to-Jesus moments for these characters where they are led kicking and screaming to the point of breaking down.  No, characters are just sad or angry for a while and then they hug it out.  That's probably how it was in real life, but it doesn't necessarily make for compelling cinema.

Honestly, the whole thing felt a little hokey to me.  It felt like an R-rated Hallmark movie.  I almost felt bad for Paul Raci, who had to play acting coach Brent Buell.  Clearly, a lot of this was a tribute to this guy who put these inmates together and got them to get over any preconceived notions.  But man, his characterization was thin.  It was a lot of corny stuff, maybe because the real guy was a bit corny.  It's hard to play something when the conflict doesn't really align with the characters portrayed.

But here's me, complaining on the Internet about a movie that is meant to make me feel good.  These guys went through a lot of crap and they came out on top.  If anything, I should be celebrating the complexities of the human soul and how art can bring out the best in anyone.  But I'm more complaining that I didn't enjoy the movie much.  Realistically, I probably would have enjoyed the documentary more.  Still, it was better than being bummed out once again with a real downer of a movie.