50 Nastiest Movie Prisoners

Thomas Highway Heartbreak Ridge (1986)

The Nasty Prisoner: “I’m mean, nasty and tired,” growls Thomas Highway (Clint Eastwood) while spending a brief spell behind bars.

Meanest Moment: “I piss napalm,” Highway tells a big hulk of a guy who dares to talk smack to him.

Though the other guy’s got a knife, Highway knows how to deal out a smackdown .

Which he does, without even breaking a sweat.

Bruce Wayne Batman Begins (2005)

The Nasty Prisoner: Bruce Wayne (Christian Bale) himself, who’s serving time at a Bhutanese prison and is, it has to be said, a bit of an arrogant schmuck at this point.

Meanest Moment: When he’s set upon by a particularly large prisoner, Wayne seizes the opportunity to show the other prisoners that he means business by bashing their heads in and breaking their legs.

“You’re not the devil. You’re practice,” he barks. Cold.

JC Blood And Bone (2009)

The Nasty Prisoner: JC (Kevin Ferguson) is a big guy (with some rather impressive facial hair), which is probably why he’s so feared in an LA jail.

You wouldn’t want to go up against this guy.

Meanest Moment: A guard’s paid off and JC confronts Isaiah (Michael Jai White) in the bathroom.

Only Isaiah’s ready for him…

Max Cady Cape Fear (1991)

The Nasty Prisoner: He wears a hairnet. He reads. And he has posters all over the goddamn walls.

Max Cady’s (Robert De Niro) a badass and he doesn’t care who knows about it.

Meanest Moment: OK, we don’t really see much of Max in prison, but it’s probably safe to assume he had all the other inmates quaking in their boots.

Dr Evil Austin Powers In Goldmember (2002)

The Nasty Prisoner: Dr Evil (Mike Myers), an evil genius who’s as bald as a coot.

He’s finally captured and imprisoned in 2002 – along with Mini-Me (Verne Troyer).

Meanest Moment: Instigating a riot.

Or that moment where he makes all the prisoners back him and Mini-Me up during a long rap scene.

Shudder.

Prisoners Harold & Kumar Escape From Guantanamo Bay (2008)

The Nasty Prisoners: A couple of terrorists in Guantanamo Bay who introduce Harold (John Cho) and Kumar (Kal Penn) to the concept of a cock-meat sandwich…

Meanest Moment: “Some call us terrorists, others call us heroes.”

One of the prisoners attempts to scare the bejesus out of Harold and Kumar.

Bronson Bronson (2008)

The Nasty Prisoner: Bronson (Tom Hardy), born Michael Peterson, who takes on the name of a famous actor when he’s released from prison – only to get locked up again after stealing a ring for the woman he loves.

He’s pretty good at fighting.

Meanest Moment: Bronson fights an old guy and marks his territory by taking a piss all over him…

Chopper Read Chopper (2000)

The Nasty Prisoner: Tattooed and darkly humorous, Chopper Read (Eric Bana) has mood swings like nobody else – alternately child-like then prone to outbursts of claret-soaked violence.

Meanest Moment: “Keithy seems to have done himself a mischief.”

Chopper feigns innocence after stabbing Keith (David Field) in a labour yard.

“You all right, Keithy? Off you go, mate. Off to the sick bay. Whinge, whinge…”

Silva Skyfall (2012)

The Nasty Prisoner: Silva (Javier Bardem), an ex-MI6 agent and full-fledged lunatic who has a thing for M (Judi Dench).

But did he orchestrate his own capture?

Meanest Moment: Silva’s far meaner on the outside than the inside, but the bit where he attempts to emotionally manipulate M by removing half his face is pretty sick .

Stan Milton Big Stan (2007)

The Nasty Prisoner: Stan Milton (Rob Schneider), a conman who ends up in prison after committing fraud.

Meanest Moment: Though Stan’s terrified of being banged up, he soon marks himself out as the biggest, craziest prisoner of the bunch when he calls out giant sexual predator Big Raymond (Bob Sapp).

Stan's plan? Snap his fingers for him…

Dawn Davenport Female Trouble (1974)

The Nasty Prisoner: Dawn Davenport (Divine), who’s sent to prison for a shotgun massacre (“Who wants to be famous?!”) and is sentenced to die in the electric chair.

Meanest Moment: Any moment she's alive. She’s the vilest of the vile, after all.

Wild Bill Wharton The Green Mile (1999)

The Nasty Prisoner: A violent criminal put on death row, ‘Wild Bill’ Wharton (Sam Rockwell) lives up to his name by turning Cold Mountain Penitentiary upside down when he arrives.

Meanest Moment: Wharton’s disdain for the guards causes him to constantly berate them and, in the case of Harry (Jeffrey DeMunn), actually urinate on them…

Danny Samson Felon (2008)

The Nasty Prisoner: Danny (Chris Browning) doesn’t hold back when he’s got a grudge, as newly interred inmate Wade Porter (Stephen Dorff) soon discovers.

Meanest Moment: While being transferred in a bus full of prisoners, Danny whips out a small blade and stabs a prisoner to death.

He then slips the knife to his buddy Snowman (Johnny Lewis) and sits simmering on the backseat…

Rocco Naked Gun 33 1/3: The Final Insult (1994)

The Nasty Prisoner: Rocco (Fred Ward), who teams up with Frank (Leslie Nielsen) when they’re banged up in prison.

Doesn’t stop Rocco being an intimidating inmate who doesn’t mind getting a bit of blood on his hands, though.

Meanest Moment: During a prison riot, Rocco twists a guard’s head right off

Youch.

Turner Im Going To Get You... Elliot Boy (1971)

The Nasty Prisoner: Turner (Anthony Weaver), the right-hand man of weed-growing prison kingping Kovick (Don Cook).

Meanest Moment: Turner’s speciality is raping new prisoners…

Boris The Animal Men In Black 3 (2012)

The Nasty Prisoner: Imprisoned on the moon for his crimes, Boris the Animal (Jemaine Clement) is one weirdo of an alien, equipped with his own deadly little hand-critter.

Meanest Moment: Does killing Nicole Scherzinger count?

Jenny Four Minutes (2006)

The Nasty Prisoner: Jenny Von Loeben (Hannah Herzsprung) is a violent inmate who flies off the handle at any given opportunity – though, as we soon discover, she’s also an incredibly talented pianist.

Meanest Moment: Jenny retaliates against another prisoner, who set fire to her cloth-bound hands, by almost killing her.

Sure it’s a revenge attack, but that doesn’t excuse her violent behaviour.

Unger The Longest Yard (1974)

The Nasty Prisoner: Unger (Charles Tyner), an arsonist inmate at the Texas State Prison.

He takes an instant dislike to new prisoner Paul Crewe (Burt Reynolds).

Meanest Moment: Unger plots to kill Crewe off by blowing up his cell.

It all goes a bit wrong, though, when a caretaker takes the full force of the explosion instead. Whoops.

Pachenko Death Race (2002)

The Nasty Prisoner: A driver in the games, Pachenko (Max Ryan) likes to throw his weight around as the prison’s Big Bad.

He also killed Ames’ (Jason Statham) wife and framed him for it.

Meanest Moment: “ It takes a big man to kill a woman.”

Pachenko confronts Ames in the canteen. And has his arse promptly handed to him.

Chasey Chaindance (1990)

The Nasty Prisoner: Serving time for embezzlement, Casey (Bruce Glover) has a real chip on his shoulder and is a meanie with far too much power on his hands.

Meanest Moment: Casey makes a desperate bid for freedom, which involves shoving an orderly’s head through a window and beating another prison into a pulp.

Amazing.

Chink Lock Up (1989)

The Nasty Prisoner: Chink Weber (Sonny Landham), who makes life a living hell for Frank Leone (Sylvester Stallone).

Meanest Moment: Killing First-Base (Larry Romano) in the gym with the help of his cronies.

Luckily, Leone soon gives Chink his just desserts.

Half Dead Penitentiary (1979)

The Nasty Prisoner: The cellmate of newly-incarcerated Gordone (Leon Isaac Kennedy), Half Dead (Badja Djola) wants to get close to Gordone.

Like, really close. And he won’t take no for an answer.

Meanest Moment: An all-out brawl occurs when Gordone continually rebuffs Half Dead’s advances.

It’s bloody and violent as hell.

Immediate promotion to ‘Daddy’.

Ericka Chained Heat (1983)

The Nasty Prisoner: Striding around in a tank-top with a cigarette clamped between her lips, Ericka (Sybil Danning) owns the halls of her penitentiary, ruling alongside Duchess (Tamara Dobson).

Meanest Moment: Ericka stands by as Carol (Linda Blair) is beaten up by a gang of lady inmates.

“Told you it pays to have friends,” she purrs, not lifting a finger.

Jake Jailbait (2003)

The Nasty Prisoner : In jail for slitting his cheating wife’s throat, Jake (Stephen Adly Guirgis) seems affable enough at first – until he starts demanding sexual favours from pasty-faced (and aptly-named) newbie Randy (Michael Pitt).

Meanest Moment: Jake’s constant switching between likeable everyman to prowling predator hits a real low when he forces Randy to perform oral sex on him – but not before beating the crap out of him.

Bellatrix Lestrange Harry Potter And The Order Of The Phoenix (2007)

The Nasty Prisoner: An insane follower of Dark Lord Voldemort, Bellatrix Lestrange (Helena Bonham Carter) was incarcerated in Azkaban for her crimes – until she managed to break out.

Meanest Moment: It’s Bellatrix who takes out Sirius Black (Gary Oldman) in the Death Chamber, blasting him through a creepy veil right in front of his nephew, one Harry Potter (Daniel Radcliffe).

Alex A Clockwork Orange (1971)

The Nasty Prisoner: Alex (Malcolm McDowell), who’s imprisoned for 14 years for killing a woman in her home.

Meanest Moment: All right, Alex doesn’t do anything particularly nasty while behind bars, but the stuff that he does beforehand is pretty awful.

Wolf Escape From Alcatraz (1979)

The Nasty Prisoner: Wolf (Bruce M. Fischer) makes a big mistake when he comes on to Frank Morris (Clint Eastwood) in the shower. That confrontation ends in Wolf getting a beating – which only makes him really angry.

Meanest Moment: Wolf confronts Frank in the yard, attempting to stab him in the back.

Except, yeah, Wolf may be nasty, but he didn’t count on Clint being so handy with a jacket.

Lofgren Bad Boys (1983)

The Nasty Prisoner: ‘Viking’ Lofgren (Clancy Brown) and Warren ‘Tweety’ Jerome (Robert Lee Rush) dominate the Rainford Juvenile Correctional Facility – despite having some truly ridiculous hairdos.

Meanest Moment: While Mick O’Brien (Sean Penn) eats lunch in the cafeteria, Viking makes it known who’s boss – which includes putting his snot in O’Brien’s food .

Maddox Fortress (1993)

The Nasty Prisoner: Backed up by compadre Stiggs (Tom Towles), Maddox (Vernon Wells) is the scariest guy in the future prison that has also become home to John (Christopher Lambert).

Meanest Moment: “You gotta pay the rent,” says Stiggs, before Maddox goes after John in the mess hall and proceeds to rip him a new one.

The fight’s bad news for Maddox, though – he has a hole blasted into him by the prison’s automated security.

Perry Smith Infamous (2006)

The Nasty Prisoner: Along with buddy Richard Hickock (Lee Pace), Smith (Daniel Craig) was responsible for the deaths of an innocent farming family – and is on death row because of it.

Meanest Moment: Though he has his meek, mild moments, Smith’s inner demon presents itself when he discovers how Truman Capote (Toby Jones) has been writing about him.

“So I’m sympathetic am I?” he hisses, almost choking Capote to death …

Loki Avengers Assemble (2012)

The Nasty Prisoner: Captured by S.H.I.E.L.D., prowling god Loki (Tom Hiddleston) is incarcerated in a hi-tech prison aboard the Helicarrier.

Thing is, he wants to be there, and uses the opportunity to create just a little carnage.

Meanest Moment: Killing poor old Agent Coulson (Clark Gregg) is pretty mean…

Carlin Scum (1979)

The Nasty Prisoner: Carlin (Ray Winston) is chucked in jail after taking the fall for his dad, who’s been thieving scrap metal.

Over the course of the film, we see Carlin transform from wet-behind-the-ears innocent to full-on badass.

Meanest Moment: Carlin puts some snooker balls into a sock and attacks Banks (John Blundell) in the shower.

Riki-Oh The Story Of Ricky (1991)

The Nasty Prisoner: Riki-Oh (Fan Siu-wong), sent to prison for 10 years and equipped with some mad skills when it comes to violence.

Meanest Moment: Too many to count, so let’s just go with the very first one, when he trips captain Samuel, causing him to land on a bit of wood with nails in it.

Of course, then Samuel sets out for (very violent) revenge…

Sofia Red Heat (1985)

The Nasty Prisoner: The kind of woman who kills other women and brands them with her own name, Sofia (Sylvia Kristen) is this prison’s top bitch.

Nobody messes with her.

Meanest Moment: Beating the stuffing out of new inmate Christina (Linda Blair) for daring to challenge her.

This is after hanging a fellow prisoner in the wash-room and scratching her name into the unfortunate woman’s forehead .

Rorschach Watchmen (2007)

The Nasty Prisoner: Framed for the murder of Moloch (Matt Frewer), Rorschach (Jackie Earle Haley) is slung in the slammer, where he makes quick work of anybody who crosses him.

Meanest Moment : Let’s just say it involves prison bars and a saw.

Watch if you dare .

The Joker The Dark Knight (2008)

The Nasty Prisoner: Locked up – albeit very briefly – after he’s caught by Gotham’s authorities, The Joker’s (Heath Ledger) time in jail mostly involves being beaten up by Batman (Christian Bale).

Meanest Moment: In order to make his escape, The Joker plants a bomb under the flesh of one of his fellow inmates.

BOOM.

Carsten R (2010)

The Nasty Prisoner: The big boss of Danish prison Horsens Statsfængsel, Carsten (Jacob Gredsted) calls all the shots and isn’t afraid to spill a little blood.

Meanest Moment: It’s not so much that Carsten gets a meanest moment as the way he constantly circles the prison like a shark, threatening to sink his teeth in at any moment.

Terrifying.

Peter & Buddies Stoic (2009)

The Nasty Prisoners: Peter (Sam Levinson), Jack (Steffen Mennekes) and Harry (Edward Furlong), who play a game of poker with Mitch (Shaun Sipos) that escalates into stomach-churning violence.

Meanest Moment: After beating Mitch and shoving his head down a toilet, Harry rapes him with a broomstick.

Mickey Natural Born Killers (1994)

The Nasty Prisoner: Mickey (Woody Harrelson) has finally been imprisoned and is about to get sent to a mental hospital when he decides to make a break for it.

Meanest Moment: Does massacring half a dozen police guards count as mean? Or just necessary ?

Bad Ass Cell 211 (2009)

The Nasty Prisoner: Bad Ass by name, bad ass by nature.

Looking more than a little like Daredevil villain Bullseye, Bad Ass (Luis Tosar) comes with a goatee to die for and zero tolerance for bullshit.

Meanest Moment: It’s more a string of moments as Bad Ass imposes his vicious, unforgiving rule over the prison.

Billy Midnight Express (1978)

The Nasty Prisoner: For most of Midnight Express , Billy (Brad Davis) is our hero – a guy who has the odds stacked against him, and whom we want to see prevail.

That’s until his four year sentence is overturned just as he’s about to complete it, and Billy transforms into an angry, violent outcast.

Meanest Moment: Billy takes out his rage on friend Rifki (Paolo Bonacelli), beating him almost to death and chewing out his tongue.

Tony Montana Scarface (1983)

The Nasty Prisoner: It’s called Freedom Town, a refugee camp, but let’s not beat around the bush, it’s really a prison.

Sent there after attempting to get into the Americas, Tony Montana (Al Pacino) makes a break for freedom by inciting a hellish uprising.

Meanest Moment: The riot at Freedom Town, where Montana shows just how merciless he can be.

Hancock Hancock (2008)

The Nasty Prisoner: Spurned superhero Hancock (Will Smith), who only really turns nasty when he’s forced to.

Banged up for his misbehaviour, he’s confronted in the mess hall by all the bad guys he ever put away.

Meanest Moment: “You sure you wanna ride this train? Choo-choo asshole.”

Hancock makes good on his promise that if two prisoners don’t get out of his way, one of them is going to have the other one’s head stuffed where the sun don’t shine…

The Duke Escape From New York (1980)

The Nasty Prisoner: “Don’t cross the Duke, everybody knows that.”

Lording over the city-sized prison that is New York, the Duke (Isaac Hayes) has declared himself the city’s leader – and you should fear him.

Meanest Moment : The Duke sets out to kill Snake (Kurt Russell) when he steals back the President.

This guy ain’t going down easy.

Cesar A Prophet (2009)

The Nasty Prisoner: The aptly-named Cesar Luciani (Niels Arestrup), who rules a French prison with an iron grip.

Meanest Moment: After taking Malik El Djebena (Tahar Rahim) under his wing, Cesar discovers that he’s been using his new power for his own gains.

Cesar’s response? Attack him with everything he’s got.

Cyrus The Virus Grissom Con Air (1997)

The Nasty Prisoner: Cyrus ‘The Virus’ Grissom (John Malkovich), a criminal mastermind who dreams of freedom.

He gets a chance at that freedom while being transported on the Jailbird…

Meanest Moment: Grissom shows he has no time for traitors when he discovers Cindino (Jesse Borrego) has been a bad boy – and kills him in cold blood.

Holding a bunny hostage is pretty mean, too.

Junior Alien 3 (1992)

The Nasty Prisoner: Though he barely utters a word while serving his time on space prison Fiorina 161, Junior (Holt McCallany) makes up for his silence with his awful actions…

Meanest Moment: A convicted rapist, Junior gives in to temptation when he corners Ripley (Sigourney Weaver) in the junkyard.

Luckily, Dillon (Charles S. Dutton) comes to her rescue.

The Sisters The Shawshank Redemption (1994)

The Nasty Prisoners: A 'bull queer' prison gang known as The Sisters, which is led by Bogs Diamond (Mark Rolston).

Their specialist? Rape of course.

Nobody ever said prison was pleasant.

Meanest Moment: Any of the times that The Sisters assault Andy Dufresne (Tim Robbins).

Neo-Nazis American History X (1998)

The Nasty Prisoner: Residents of the California Institution for Men, the neo-Nazis are members of the Aryan Brotherhood.

They turn on Derek (Edward Norton) when he tires of their prison politics.

Meanest Moment: When Derek gets close to other inmate Lamont (Guy Torry), the neo-Nazis punish him by assaulting him in the shower.

Brutal.

Hannibal Lecter Silence Of The Lambs (1991)

The Nasty Prisoner: Hannibal The Cannibal (Anthony Hopkins), who’s been incarcerated in the Baltimore State Hospital for the Criminally Insane.

OK, so he’s technically not in a conventional prison – but he’s definitely being held against his will.

Meanest Moment: As if scraping around inside young Starling’s (Jodie Foster) head wasn’t enough, Lecter goes on to kill two guards during a bloody (and successful) escape attempt.