I know that everyone was excited about the New York Times’ Greatest Movies Of the 2000’s, a collaborative effort that ignored a lot of great movies, boosted a few that have already been worshiped by movie fans, and generally (hopefully) gave people something new to discuss.
I remember when I was in college, and I decided to do my own project, trying to see all the great and adventurous movies that had been released during my lifetime. It seemed like an impossible task, never to be properly finished. Looking back, obviously, I was dealing with less actual years than the people participating in this survey actually were. And my participation has to take into account all the great movies I missed while in prison, the sole reason for this site (I’ve seen far more than I’ve written about since I got out, for the record).
Rust + Bone (d. Jacques Audiard)
Audience Of One (d. Michael Jacobs)
Nomadland (d. Chloe Zhao)
Computer Chess (d. Andrew Bujalski)
Never Rarely Sometimes Always (d. Eliza Hittman)
Another Year (d. Mike Leigh)
Trouble Every Day (d. Claire Denis)
Seediq Bale: Warriors Of The Rainbow (d. Wei Te-sheng)
Bones And All (d. Luca Guadagnino)
The Sound of Noise (d. Ola Simonsson, Johannes Stjarne Nilsson))
Neighboring Sounds (d. Kleber Mendoca Filho)
Killing Them Softly (d. Andrew Dominik)
Cache (d. Michael Haneke)
A Town Called Panic (d. Stephanie Aubier, Vincent Patar)
Demonlover (d. Olivier Assayas)
Sugar (d. Ryan Fleck, Anna Boden)
The Last Circus (d. Alex de la Iglesia)
The Fountain (d. Darren Aronofsky)
Tar (d. Todd Field)
Morvern Callar (d. Lynne Ramsay)
Fat Girl (d. Catherine Breillat)
Bright Star (d, Jane Campion)
Bamboozled (d. Spike Lee)
Certified Copy (d. Abbas Kiarostami)
Margaret (d. Kenneth Lonergan)
Ghost Dog: The Way Of The Samurai (d. Jim Jarmusch)
35 Shots Of Rum (d. Claire Denis)
Oldboy (d. Chan Wook-Park)
Synecdoche, New York (d. Charlie Kaufman)
There. There’s your thirty. Tomorrow it may be thirty different ones. There may be Gaspar Noe, there might be some Bollywood. I might do a John Waters and put in the brilliant “Butt Boy”. But whatever, I’d just be saying, look at my taste! (And maybe, look how many Nolans I DON’T have in there, aren’t I a maverick?) Anyway, I have a Letterboxd, forward all complaints there (where I review a ton of 2025 movies).
Instead, I want to focus on the movies I felt had something to say about criminal justice. Movies that, in one way or another, tackled the depths of depravity of why we have a criminal justice system and what does it do, to whom, and for what purpose. Many of these movies are not explicitly about prison, because the idea of being in prison can seem like an abstract notion. Indeed, if I can give you only ONE movie that properly conveys what life in prison is like, I would keep returning to 1971’s “Wake In Fright”, which is Australian and not at all about incarceration.
Here are fifteen movies from the last twenty five years that advocate for, in one way or another, an end to the violation that is mass incarceration.
(Apologies to Garrett Bradley’s “Time” and Brett Story’s “The Prison In 12 Landscapes”, neither of which I have seen yet, though I’d bet they’d be worthy of a mention here).
Sorry To Bother You (d. Boots Riley)— Riley’s scabrous directorial debut is a vicious takedown of predatory capitalism, a system puppeteered by the same masters of industry that would otherwise have their fingers shoved deep inside the world of private prisons and the military industrial complex.
Rebel Ridge (d. Jeremy Sauliner) — A conventional pulse-pounding thriller that’s also a pivotal reminder of civil asset forfeiture, and how authorities freely wield this power over the unfortunate.
Nickel Boys (d. RaMell Ross) — A sharply evocative tale of wounded Black bodies in captivity, “Nickel Boys” illustrates the difficulties of the marginalized to illustrate and express their mistreatment.
Never Let Me Go (d. Mark Romanek) — Elegiac British science fiction about how we accept and condone oppressive systems even when we are the oppressed.
Queen And Slim (d. Melina Matsoukas) — Carefully illustrates the racism ingrained in modern law enforcement.
Selma (d. Ava DuVernay) — One of the first accounts of Dr. Martin Luther King Jr.’s life to properly contextualize the FBI’s malevolent, unlawful treatment of him. Also see: “Judas And The Black Messiah”.
This Is Not A Film (d. Jafar Panahi) — He was told by the courts he was facing six years in an Iranian prison, and twenty years without being allowed to make films. Instead, under house arrest, Punk Rock Panahi made this.
The White Ribbon (d. Michael Haneke) — In the early 1900’s, a terrible accident caused by children in Eastern Germany forces a small community to clash over what sort of punishment is appropriate, or if one is appropriate at all. Through a contemporary lens, a movie about so much, but particularly how sloppy and arbitrary we can be when we decide to “punish”, particularly those close to use.
Elite Squad/Elite Squad: The Enemy Within (d. Jose Padilha) — Two propulsive action films that also carefully lay out what makes one’s politics change when entering law enforcement.
If Beale Street Could Talk (d. Barry Jenkins) — Powerfully illustrates how we lose power and lose humanity when we end up in cuffs.
The 25th Hour (d. Spike Lee) — What you lose inside yourself before you report to prison.
Sing Sing (d. Greg Kwedar) — Tellingly, the one movie in the last couple of decades to show the greatest sense of empathy to prisoners.
Compliance (d. Craig Zobel) — Upsetting sort-of-based-on-real-life thriller about a man who impersonated law enforcement over the phone, threatening people with incarceration if his increasingly arbitrary demands weren’t followed. Stories like this are why we have prisons.
The Act Of Killing/The Look Of Silence (d. Joshua Oppenheimer, Christine Cynn, Anonymous) — A damning indictment of how some societies (all?) treats the “winners” of mass murders and genocide.
The 13th (d. Ava DuVernay) — The most stirring and informative document on the rise of mass incarceration in America, a MUST-SEE for anyone with an interest in the prison-industrial complex.
Watch the entire movie for free, legally, here!
And on my one year anniversary, the song that saved my life many times while I was incarcerated:
I thought I was going to take a few minutes to read this second bonus weekend post and then finally get around to listening to your stint as podcast guest, but no skimming through this quickly and moving on. A lot to reflect on, and some good new (to me) finds.
If you aren't already working on a semi-autobiographical screenplay, you should be (you probably have enough material for a franchise ;) ).
*The link in your post for The Act of Killing/The Look of Silence leads to your previous post on The End-I appreciated a chance to read it, but I'm assuming this isn't the intended target of that link.
The Act of Killing is one of the most unsettling documentaries ever made. It forces you to witness how people normalize and justify atrocities. It’s the kind of film that haunts you. Thanks for mentioning it.