Locked Up: The 10 Best Movie Prisoners

Elias Stein

Did you know that earlier this week we celebrated the 25th anniversary of Death Warrant? Do you even know what Death Warrant is? Death Warrant is a movie in which Jean-Claude Van Damme plays a member of the Royal Canadian Mounted Police who poses as an inmate in a California prison. He does so to help the governor figure out why so many unexplained deaths are occurring in the prison.

As it turns out, the prisoners are having their organs harvested, which is either a very good idea or a very terrible thing, depending on what type of politician you are. The movie ended with JCVD karate-kicking the main bad guy into a furnace and then that same guy getting his head impaled with a spike after he jumped out of the furnace. And we know that all of this sounds very ridiculous, and that’s because it is all very ridiculous. Nevertheless, Death Warrant is actually a steady, competent prison movie. So we, Jason Concepcion and Shea Serrano, are using its anniversary as an excuse to take public a conversation we’ve been having in private for the past few months. This article is about prisoners in movies. More specifically, we’re deciding who is the best, greatest, most perfect, most aptly portrayed, most compelling, most interesting prisoner in a movie.

As always, we set rules in place to make the task more manageable:

  1. You can’t pick more than one prisoner from the same movie. This is the Blood in, Blood Out rule. Prisons are lush character communities, and so movies about them (good movies, anyway) often have upward of five, six, or seven strongly acted roles. Blood in, Blood Out’s San Quentin had at its center Miklo and El Mero Mero philosophically wrestling over morality, but it also had Big Al (white supremacist cook who ran the gambling ring), Bonafide (leader of the black guerrilla army), Popeye Saavedra (lowlife prison pimp), and Magic (El Mero Mero’s second-in-command). So to prevent any one movie from dominating the top 10, the rule here is you can’t pick more than one prisoner from a movie.
  2. You can’t pick a prisoner from a movie based on an actual person. This is the Denzel Washington in The Hurricane rule.
  3. The prison does not have to be limited to a standard, prototypical facility. This is the Con Air rule. Things like Space Prison (Lockout) or Airplane Prison (Con Air) or Boys’ Home Prisons (Bad Boys, Sleepers, etc) or Mental Health Prisons (a bunch of movies) and institutions of that nature are OK. Really, for the purposes of this article, we just went ahead and considered any place that detained people.

But before we get to the top 10, we have some awards to hand out.

The Best Monologue

Jason: Grossberger singing “Down in the Valley.

When we first see Grossberger in the 1980 buddy prison comedy Stir Crazy, he’s eating alone in the prison mess hall, scowling, hunched over his meal, one meaty arm draped in front of his food like a Cerberus, looking like 400 pounds of very bad news.

Comedy is about subverting expectations, though, so when the wardens move Grossberger into Skip (Gene Wilder) and Harry’s (Richard Pryor) cell in a bid to break the pair of their city-slicker truculence, we aren’t too surprised when, come next cell count, the trio are suddenly thick as thieves and happily cheating each other at cards.

What does surprise is Grossberger — played by the late Erland van Lidth, an Olympic-alternate wrestler and opera singer with a degree in computer science from MIT — suddenly launching into a sensitive a cappella version of “Down in the Valley,” his lilting baritone filling the cell block like the sound of a broken heart.

Shea: This is a sneaky-clever pick for this category. I’m going traditional. I’m going with Luke’s lost-man one-way conversation with God in an abandoned old church at the end of Cool Hand Luke:

More on Luke later.

The Best Escape Artist

Jason: Andy Dufresne in The Shawshank Redemption. Could it be anyone else?

Shea: You know what? I get that pick. I understand that pick. Andy Dufresne certainly showed the most dogged perseverance and determination of any of the prison movie escapees, what with him escaping from a prison one handful of dirt and rocks at a time over something like 20 years. But how about this: Maybe we consider the idea that he actually wasn’t that great at escaping?

There’s a natural inclination to just stand in awe of the amount of time he spent getting out and assume that means his escape was the most fantastic, but just because something takes a long time doesn’t automatically mean it’s the best. I mean, Nas recorded “N.Y. State of Mind” in one take, you know what I’m saying? So allow me to enter another name in this category: Woody in Toy Story 3, which was absolutely a prison movie. He was in that day care torture chamber for all of one day and was like, “OK, I gotta get the fuck outta here,” and then guess what. He got the fuck outta there. And not only that, but after Woody broke out of prison, he broke back into prison, rescued his friends, and then broke back out of prison again. That’s real moxie. That’s a real escape artist.

The Best Prisoner Who Wasn’t the Main Prisoner

Jason: Glenn from 1998’s Out of Sight.

I distinctly remember, after seeing this movie in the theater in ’98, thinking something like, Steve Zahn is going to be a huge star. I didn’t quite count on Zahn being that weird sort of actor with a healthy work-life balance who prefers nature to being in Los Angeles lunch meetings and would probably rather be fishing than doing anything else.1 In 2008, Zahn was interviewed by Outdoor magazine for a piece that was subtitled “How to be a Hollywood star and still get outside 267 days a year” and said of his career up to that point: “You know, a lot of these things started because I would work half the time on a movie and then hang out. And now I’m playing more involved roles, I’m more pinned down, which is frustrating. I get just a day off. What are you going to do with that?”

Anyway, Glenn — the most criminal thing that happens in this movie is the way Glenn stole scenes.

Shea: Ha. I felt that exact same way watching Zahn in That Thing You Do! But I’m giving my pick here to the aforementioned Big Al from Blood in, Blood Out. He was awful and dirty-looking and racist and obnoxious. In his most memorable scene, he turns handing out pork chops into a master class in being despicable. He pickles each of the different races with laser-straight barbs. He alternates between greasy salesman and hatemonger with nary a stitch, let alone a seam. There is an emptiness in his heart. He’s definitely not Glenn.

The Best Prison Bad Guy

Jason: Hannibal Lecter, Manhunter/The Silence of the Lambs.

Things that Hannibal Lecter manages to pull of while in prison:2

  • Hacks a telephone using a gum wrapper
  • Socially engineers a receptionist at the University of Chicago into giving him FBI agent Will Graham’s home address
  • Manages — while incarcerated, mind you — to send a coded message to the serial killer Francis Dollarhyde imploring him to go to Will Graham’s home and “save yourself; kill them all”
  • Convinces another prisoner in an adjoining cell to commit suicide by swallowing his own tongue
  • Uses the kidnapping of a senator’s daughter to talk his way into a meeting with said senator, which unfolds like the serial-killer version of a Thug Life meme
  • While locked in full-body restraints and face mask, steals a pen, breaking off and swallowing the clip piece
  • Picks his cuffs with the pen clip, then kills two guards and disguises himself with one’s torn-off face

Shea: That’s quite a list of terrible things Dr. Lecter did. But here’s the truth about Hannibal: Not getting killed or maimed or eaten by him mostly seemed like an easy thing to do. All you had to do was (1) don’t be rude; (2) don’t try to catch him, and if you do try to catch him, then be Clarice Starling because he has infinite respect for her; and (3) if you happen to be in an orchestra, don’t be out of tune. If you do those things, then you’re safe. Plus, and this is just a personal thing, but I’ve always found Hannibal kind of charming and definitely interesting. So, yes, technically he’s a bad guy, but also he’s a guy I don’t mind rooting for, which I guess means he isn’t entirely bad, or if he is entirely bad then he’s at least a fun kind of entirely bad. That’s why I can’t pick him as my best prison bad guy. There’s only one guy in this category for me: Sean Nokes (Kevin Bacon) from Sleepers.

Do you remember him? If you saw Sleepers, then of course you do. If not, let me tell you all that you need to know about him: He was the ringleader of a group of guards in an all-boys juvenile detention facility who enjoyed doing terrible things to children. No parts of him were good. No parts of him were likable. There was never a moment in that movie when he did or said something that made me go, “Maybe he’s actually not the worst person.” Sean Nokes was murdered in Sleepers, and he absolutely deserved it. That’s always been the best way for me to determine who is truly a bad guy.

The Most Devastating Prison Death Scene

Jason: Caretaker (Jim Hampton) in The Longest Yard (the 1974 version, not the 2005 version). All he wanted to do was manage the prison football team and instead he got burned alive by an exploding light bulb that wasn’t even meant for him.

Shea: Fair. But I think I might have a better one. Or a “worse” one? I’m not sure what’s the right adjective to use here. “Better” seems weird when you’re talking about death. You know what, though? It doesn’t matter. Because my death scene isn’t even actually a death scene, in that the guy who dies doesn’t all the way die. Have you seen Starred Up?

A basic summary of the movie: An extremely angry (and violent) teenager gets moved from a juvenile detention facility to adult prison. And it’s the same one, mind you, where his father, also extremely angry (and violent), is housed. The two, obviously, can’t stand each other, but really it’s more that the son can’t stand the dad. A lot of stuff happens and it’s all tense and dramatic and you really have to watch it to get a proper understanding of how uncomfortable and packed full of nervous energy it is. (The teenager, Eric, played superbly by Jack O’Connell, goes something like 10 minutes on camera before he says even a word.) The movie ends with the guards staging Eric’s suicide, hanging him from an air grate in his room. His dad walks in, sees his son dangling, and starts fighting through the guards to save him, ALL WHILE ERIC IS BEING STRANGLED TO DEATH. When the dad finally gets to him, it’s too late. Eric’s hanging there, just meat and bones but no life. And his dad is just broken and devastated and it’s so bad to watch.

BUT THE THING OF IT IS: Just when you’ve given up hope, when you’ve accepted that you’ve just watched this man watch his son die in front of him, Eric takes a breath. He wakes up, he’s wheezing and coughing, and when he gets his wits about him, he just starts crying and oh, man, great, now I’m crying again.

The Prisoner Most Likely to Turn His or Her Life Around After Getting Out of Prison

Jason: Annie from Annie.

Shea: Very solid pick. Initially, I was going to offer up Derek from American History X, but I have a new pick, a better pick, a pick that we actually can 100 percent confirm was able to get it together. I’m going with Viking from 1983’s Bad Boys. He was the alpha predator at the Rainford Juvenile Correctional Facility. This is him:

Do you know who he ended up growing up to be? I’ll tell you who: The hardest screw that ever walked a turn at Shawshank State Prison:

shawshankd_screwColumbia Pictures

Viking was so moved and positively affected by his time at Rainford that he went straight, dedicating his life to helping rehabilitate prisoners himself. He killed a man and then also crippled another during his reign at Shawshank, so maybe you’re thinking he didn’t actually turn anything around. But if you squint you can see he was actually just acting in the best interests of his prisoners. When he killed that one guy, for example, it was because he was making too much noise at night and nobody could get any sleep — and sleep is very important, especially when your days are filled with the angst and anger of imprisonment. And when he crippled that other guy it was because he was defending Andy Dufresne’s honor, which is actually very sweet. You say he was being maniacal. I say he was just being very good at his job.

The Prisoner Least Likely to Turn His or Her Life Around After Getting Out of Prison

Jason: Hannibal Lecter.

Please see the above list.

Did I mention he enjoys eating people and has a refined, foodie’s sense of how to prepare and eat human flesh? That’s not going to change under any circumstances. He’s the Anthony Bourdain of people-meat.

Shea: The chickens in Chicken Run. Because they’re chickens.

The Movie Prisoner Most Likely to Survive If He or She Were Actually Sent to Prison

Jason: Agent Snow from Lockout.

The Luc Besson–produced Lockout is basically Escape From New York but in space jail. Guy Pearce plays defrocked CIA agent Marion Snow. Snow has been framed for murder and treason and is the kind of hard-boiled character who says stuff like, “People love me; just ask your wife,” to an interrogator while being repeatedly punched in the face. He’s just the kind of highly trained, born-to-lose hardass you need when Emilie Warnock, the president’s estranged, bleeding-heart daughter, gets herself caught up in a hostage situation on MS One. (The aforementioned space jail.) Later he hands Emilie a shotgun and tells her, “Here’s an apple. And a gun. Don’t talk to strangers.” This guy has had his ass kicked by professional spies and trained killers and survived orbital reentry without a spaceship. Regular old Earth jail wouldn’t be a problem.

Shea: Jason, look, I think in most any other situation I would’ve been swayed by your Space Jail vs. Earth Jail argument, because I think that is a very astute observation. But we have a real-life answer to this one: Wesley Snipes. He played inmate Monroe Hutchen in Undisputed and then he played inmate Wesley Snipes for nearly two and a half years at McKean Federal Correctional Institute in Pennsylvania. He came out unscathed. Nobody’s fucking with Blade.

The Movie Prisoner Least Likely to Survive If He or She Were Actually Sent to Prison

Jason: Ernest from Ernest Goes to Jail.

Ernest P. Worrell was a character created by a Nashville advertising agency as kind of an Everyman Jubilation T. Cornpone, the type of good ole dude who you’d sure-nuff buy a new or pre-owned Toyota from because the guy is simply too dumb to lie. When, in what could only have involved a deal with Lucifer himself, Ernest somehow made the jump to the big screen,3 he became the idiot triumphant who succeeds in all manner of situations because he’s too dumb to quit or realize how screwed he is. In real life, in the actual general population, this dude would get shivved within the first five minutes of arriving on the cell block.

Shea: Fair. An alternate here might be DJ Qualls’s Dizzy from The New Guy. He got all his prison advice from Eddie Griffin, who is about as intimidating as a bag of marshmallows. And his best fight move wasn’t even a fight move; it was just him making one of his eyes bigger than the other one:

FOH, Dizzy. RIP, Dizzy.

Let’s go over the guys who were picked as the 10 best prisoners, none of whom are from Con Air, which I am especially embarrassed about:

10. Jack Foley, Out of Sight

Jason: Jack Foley (George Clooney at his most rakishly charming) is an inveterate bank robber with multiple convictions, the leader of a small-time crew specializing in B&E’s and thievery, and a recent escaped prisoner from a federal penitentiary. And yet you can’t help but like the guy. Certainly, U.S. Marshal Karen Sisco couldn’t help it. She falls for Foley — and he for her — after being forced to ride with him in the trunk of her own car after stumbling upon an in-progress jailbreak. Out of Sight, directed by Steven Soderbergh and based on the Elmore Leonard novel of the same name, is a small miracle of a crime movie. Funny, bracingly violent, gritty, and — against all odds — romantic.

9. Yates, The Last Castle

Shea: There’s this thing that Mark Ruffalo does with his face, this very condescending and treacherous look — this look that says, “I can’t be trusted,” this look that says, “I’m not what I seem,” this look that says, “I’m eventually going to deceive you,” this look that says, “I have a very strong amount of contempt for you and everything that you stand for,” this look that says, “I’m no good and you know it but you don’t want to know it.”

Occasionally, it can serve to unravel the intention of the roles he plays, but when he’s cast in a movie that requires him to have an air of superiority (Foxcatcher), or operate under a false pretense (The Avengers, Shutter Island, Now You See Me), or be unpredictable in a way that’s supposed to make you feel uncomfortable — which is what he did as the unlikable soldier-convict Yates in The Last Castle — he is goddamn unstoppable.

Yates was dismissive and so thoroughly glib in the face of even the most sincere honesty that he made it feel like he’d crawled inside your skin and left you coated in slime. Even after he’d made it obvious that he’d turned good and sided with Robert Redford’s moral superhero Lieutenant General Eugene Irwin, even after he’d heroically jeopardized his own life to save the lives of others, you still didn’t allow yourself to completely trust him. Generating that sort of tension isn’t easy, but it’s required of a certain kind of movie prisoner, and I’m not so certain that anyone’s ever done it better than the way Ruffalo’s Yates does it here.

8. Skip and Harry, Stir Crazy

Jason: I’m cheating here, but these two can’t be split up. One of my favorite buddy movies of all time, Stir Crazy tells the story of two New York City friends, Skip (Gene Wilder) and Harry (Richard Pryor), who both lose their jobs on the same day. Skip, a store detective, falsely accuses an actress of shoplifting and being naked under her overcoat while Harry, a waiter/butler, accidentally feeds an upper-class dinner party generous helpings of food spiked with his stash of extremely potent weed.

The two decide to seek their fortunes out west. Somewhere in the Southwest, they end up framed for a bank robbery and sentenced to matching 125-year prison sentences. High jinks ensue. Eventually, the two get wrapped up in, what else, a prison rodeo competition, because of Skip’s incongruous natural talent for riding livestock. But the plot doesn’t really matter. What matters is Wilder and Pryor’s chemistry. Skip is the stereotypical white Northeast liberal, the kind of guy who happily hands the warden a handwritten list of potential improvements for the prison administration and genuinely expects him to take it seriously. Harry is the realist, the guy who’s contemplated being devoured by the machine, and is therefore often openly, and hilariously, terrified by their predicament.4 One of the best onscreen comedy duos ever.

7. John Coffey, The Green Mile

Shea: Honestly, I’m surprised Coffey didn’t finish higher. He’s the only prisoner here who was plugged into the universe, the only one who could subtract sicknesses from humans, the only one who was truly a divine figure. I’m not sure what else he needed to do. The only explanation I could think of for him landing way back at no. 7 is he never truly felt like a prisoner — or if he did, then it was as a prisoner of his own existence and not the prison where he was incarcerated. I guess that’s important.

6. Lotso, Toy Story 3

Jason: Lotso’s easygoing voice (the great Ned Beatty) and cuddly-bear appearance masked a cruel, authoritarian personality that, again, concealed the trauma of his abandonment. Lotso’s heart was twisted by the realization that he was just a disposable item, replaceable, a toy. And that knowledge turned him into one evil son-of-a-sow who ruled Sunnyside with a plush iron fist. But that tragic backstory also gives Lotso a humanity (what the hell do Buzz and Woody — a couple of coddled idiots — understand about the vagaries of life?) and made his denouement, spending eternity tied to the front of a garbage truck, seem almost too harsh a punishment. Even for him.

5. Sylvester Stallone in Victory (1981) / First Blood (1982) / Rambo: First Blood Part II (1985) / Over the Top (1987) / Rambo III (1988) / Lock Up (1989) / Tango & Cash (1989) / Demolition Man (1993) / Judge Dredd (1995) / Escape Plan (2013)

Shea: He was a prisoner at some point in each of the above movies. Can you even believe that? I suppose if I had to pick one of those roles as being better than the others, though, then his portrayal as Frank Leone in Lock Up — where he mostly just wallowed around inside his own sad eyes, which he has always been good at — wins this spot. (Tango & Cash was a more fun movie, but Lock Up was a “better” movie.)

I’ve always been at least a little bit surprised by how underappreciated Lock Up is, especially when you consider that it has the best prison movie football game of all time. That top five goes:

5. The futbol game in Mean Machine. Shout-out the Monk for almost single-handedly costing his team that game.

4. The football game in 1974’s The Longest Yard. Shout-out Burt Reynolds’s eyebrows.

3. The football game in Sleepers. Shout-out Rizzo, but also rest in peace Rizzo.5

2. The football game in 2005’s The Longest Yard. Shout-out 88.

1. The football game in Lock Up:

Shout-out Eclipse. I would give my life for Eclipse.

4. Annie, Annie

Jason: YES, I SAID ANNIE, SON. YES, I AM COUNTING AN ORPHANAGE RUN BY SKEEZY, WELFARE-CHEAT BOOZEHOUNDS AS A PRISON. So why Annie and not, say, Oliver Twist or even Sleepers? Because of the bangers, man. You can’t nod your head to Sleepers. “It’s a Hard-Knock Life”? Fire. “Tomorrow”? Straight blue flames. “You’re Never Fully Dressed Without a Smile”? An important life lesson. And is there a better rap name in all the great American songbook than Daddy Warbucks, a.k.a. Will Stacks, a.k.a. General Ollie Warbucks? Annie, son.

3. Miklo Velka, Blood in, Blood Out

Shea: Miklo Velka, the biracial Angeleno who rose from barely wanted foot soldier of a piddling neighborhood gang to the head of La Onda, an ultra-powerful Mexican prison gang, is my all-time favorite movie prisoner and also my all-time favorite movie character from my all-time favorite movie. I’m devastated that he didn’t end up in the no. 1 slot. I suppose it makes sense, though. Miklo’s been underestimated his whole life. Why should this scenario be any different?

These are the 10 questions you have to ask yourself if you have eyes on becoming an iconic, top-tier, grade-A, first-class movie prisoner:

  1. Are you caught betwixt conditions that prove to be a life-defining quandary?
  2. Are you from a broken home and in search of something resembling a family?
  3. Have you had some sort of insecurity beaten into your body by the world at large?
  4. Are you capable of being fiercely loyal?
  5. Are you capable of plotting and executing the murder of someone you were once fiercely loyal to?
  6. Are you aspirational?
  7. Are you kind of a moron in the real world but hyperintelligent in a prison setting?
  8. Are you the victim of an unfortunate catastrophe?
  9. Are you so consumed with anger and passion that you’re able to make your irrational logic sound like a very good plan, and then also driven enough and determined enough to actually turn it into a very good plan?
  10. Are you potentially a good person at your core but you’ve had your core eroded by circumstance?

If you can answer “yes” to more than seven of those questions, you have a very good shot at making it into the elite sector. Miklo, snakebit by destiny, answers yes to all 10.

  1. His father was white and his mother was Mexican and he desperately wanted to be viewed as Mexican but was discriminated against because he had blond hair and blue eyes. It was the defining dilemma of his life. He had to kill a man before his own cousin would accept him as a Mexican. And then after he went to prison for murder, he had to kill another man to get the Mexicans in there to accept him.
  2. His father disowned him and then his mother disowned him, too. We never see or hear from either of them again after the first six minutes of the movie.
  3. Because of the white/Mexican thing.
  4. He dedicated his life to his neighborhood gang, Vatos Locos, and then dedicated his life to serving El Mero Mero, the leader of La Onda, after he arrived in prison.
  5. After deciding he disagreed with the ideology El Mero Mero was trying to imprint on La Onda, he set in place an especially elaborate plan to kill El Mero Mero.
  6. He wanted to be the leader of La Onda.
  7. He was a perpetual loser outside San Quentin. Inside San Quentin, though, he was so powerful a figure that he was referred to as “God” by one of the people trying to stop him. His shining achievement: orchestrating the mass murder of 17 inmates without ever being in a room with even one of the victims.
  8. His cousin shot him in the leg, which resulted in him having to have his leg amputated from under the knee down.
  9. I’m going to direct you back to no. 7.
  10. He was clearly a sincere, loving, good-natured person at the start of the movie (and even up through his first prison stint, the murder of Big Al notwithstanding). By the end of the movie, he was all the way rotten, all the way evil.

I need my inmates star-crossed. I need my inmates devastated by life. I need my inmates unstoppably ambitious. I need my inmates forever unsettled. I need Miklo Velka.

2. Andy Dufresne, The Shawshank Redemption

Jason: If you’ve ever watched a true-crime show — 48 Hours, Cold Justice, or pretty much any program on the Investigation Discovery channel — you’ll see a case where some version of “he just didn’t act the way an innocent/grieving husband should act” comes up. That was Andy Dufresne’s biggest problem; he comes off as aloof, professorial, a tad on the frosty side. Which is fine for an ace accountant and tax preparer, but not a great asset when your task is to convince a small-town jury of your peers that you didn’t kill your wife and her lover.

Ironically, as it turns out, that head-in-the-clouds quality, that air he has of not quite being present — what his buddy Red would describe as the look of a free man — is what kept Andy alive in prison. It’s what allowed him to survive the near daily degradations of his fellow inmates. And it’s what allowed him to dream up and execute a fantastic near-two-decade escape that resulted not just in his comfortable exile in Mexico but in the downfall of the brutal and corrupt Shawshank prison administration.

1. Lucas “Luke” Jackson, Cool Hand Luke

Shea: Nobody hurt more. Nobody was more broken. Nobody was more devastating. Nobody was more devastated. Nobody was cooler. Nobody was more irrepressible. Nobody was more repressed. Nobody was less capable of dealing with the intellectual restrictions of imprisonment. Nobody was more blessed by his own creation. Nobody was more jilted by his own creation. Nobody evoked more empathy. Nobody evoked more envy. Nobody had more pathos. Nobody was more propelled by his own ethos. Nobody was more undone by his own ethos.

Nobody was more anything than Cool Hand Luke.

Nobody was a more perfect movie prisoner.

Filed Under: Movies, the shawshank redemption, cool hand luke, Blood in Blood Out, annie, Toy Story 3, Lock Up, Death Warrant, Sylvester Stallone, Out of Sight, The Green Mile, Hannibal Lecter, Stir Crazy, Paul Newman, Tim Robbins, Michael Clarke Duncan