The 40 Best Prisoners in Pop Culture

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Most of us at the Paste office have already binge-watched the first season of Orange Is the New Black and enjoyed getting to know Piper, Red, Taystee and (especially) Crazy Eyes. But while we wait for their return (Netflix has yet to announce dates for Season 2), we turn our attention to some of the great pop-culture prisoners who’ve come before.

We’ve limited ourselves to one entry per book, movie, game, song, TV show, etc., so it wouldn’t just be the cast from Oz. Let us know who we missed (or if you’re feeling particular encouraging—what we got right) in the comments section below.

Ryan Bort, Burgess Brown, Sean Doyle, Patrick Filbin, Josh Jackson, Tyler Kane, Garrett Martin, Bonnie Stiernberg contributed to this story.

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40. Otis Campbell (The Andy Griffith Show)
Mayberry’s town is so laid-back that its most frequent criminal is free to check himself into the town jail whenever he wants. Otis Campbell has been an inspiration to bloated, ruddy-faced, Southern alcoholics for nigh on 50 years now.—GM

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39. Steven Russell (I Love You Philip Morris)
Some people don’t learn from their mistakes, and that’s quadruply true for on-again/off-again prisoner Steven Russell in I Love You Philip Morris. His multiple breakouts (and following returns) see Jim Carrey’s pitch-perfect character as a con-man in every sense of the word, wooing (and losing) his new love Philip by refusing to let four walls hold him back.—TK

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38. Frank Morris (Escape from Alcatraz)
Clint Eastwood  plays bank robber Frank Morris, who is sent to Alcatraz after already having escaped from several other prisons. Morris eventually realizes that some of the concrete in his cell can be chiseled away, so he and some of the other inmates he befriends start chipping away with sharpened spoons. An escape is made, and the movie ends with Morris and company paddling away on a raft they fashioned out of raincoats.—RB

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37. Dae-su (Oldboy)
When you say the word “prisoner,” you expect a few things: Bland, concrete quarters; orange jumpers and a relationship with maybe a too-close-for-comfort cellmate. But Oldboy showed us a different side of captivity with Oh Dae-su, a businessman who is confined to a hotel-like space for almost 15 years without explanation. After a surprise release, Dae-su has to track down the reason for his imprisonment or his love interest Mi-do will be killed. Sadly, the twisted trek through Dae-su’s captivity unravels a punishment worse than a lifetime away from civilization.—TK

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36. Fontaine (Robert Bresson’s A Man Escaped)
It’s not necessarily who he is but how he escapes that makes Fontaine so memorable. Robert Bresson’s film focuses like a laser beam on the French Resistance member’s patient and meticulously planned escape from a Nazi prison, contrasting the severity of the situation with the same steadiness and cool head with which Fontaine carries out his escape.—GM

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35. Col. Robert E. Hogan (Hogan’s Heroes)
The leader of the Allied prisoners in the Nazi POW camp, Hogan didn’t let his capture get in the way of making a difference in the war. When the loose-with-the-rules Air Force colonel wasn’t flirting with Col. Klink’s secretaries, he was masterminding operation after operation under the nose of Klink and Sargeant Schultz (“I see nothing!), who were more concerned about getting transferred to the Russian front than to stop Hogan and his heroes.

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34. Edmond Dantès (The Count of Monte Cristo by Alexander Dumas)
French author Alexander Dumas’ revenge tale has been adapted for the screen more than 20 times (including three gender-switching versions of The Countess of Monte Cristo). It’s spawned two musicals. And it became a best-selling novel throughout Europe when it was first published in 1946. Dantès was arrested on the eve of his wedding by three jealous friends who falsely accuse him of being an English spy. He was no spy before his arrest, but the way he devises an intricate plot to get back at those who’ve wronged him, assuming the identity of the count when he inherits his fortune, would do James Bond proud.—JJ

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33. Charles Bronson (Bronson)
Starring Tom Hardy as Charles Bronson (not that Charles Bronson), Bronson is based on a true story of an infamous British prisoner of the same name who has been in and (briefly) out of prison his entire life, developing a reputation for administering beatings to inmates and guards alike, taking hostages and generally stirring up a world of trouble wherever he goes. It’s hard to imagine anyone embracing life behind bars quite like Charles Bronson, who practically made a sport of it.—RB

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32. Astronaut Taylor (Planet of the Apes)
After an air leak causes Taylor’s ship’s suspended animation systems to fail, he awakes to find Earth is being run by a caste system of great apes. After escaping imprisonment, castration and threats of lobotimy, Taylor finds the answers he’s been looking for about just where exactly he crash-landed….”YOU MANIACS! YOU BLEW IT UP! OH, DAMN YOU! GODDAMN YOU ALL TO HELL!”—SD

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31. Johnny 99 (“Johnny 99” by Bruce Springsteen)
Springsteen’s most iconic antihero and an outlaw who had no other way out of the “debts no honest man could pay” appears on Nebraska. It’s hard to be sympathetic towards Johnny, but his last statements to Mean John Brown might make you think otherwise.—PF

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30. Paul Crewe (The Longest Yard)
It goes without saying that we’re talking about the original version of the film starring Burt Reynolds, not Adam Sandler’s 2005 debacle of a remake. Paul Crewe is an ex-football-player-turned-convict who fills the classic role of an inmate/protagonist who is initially despised by his fellow prisoners but ends up winning their favor. He leads a football team of inmates against the team of guards whom Crewe refused to coach. Not often are comedies set inside a jailhouse, but it works with The Longest Yard.

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29. Dr. Evil & Mini Me (Austin Powers in Goldmember)
Forget that river of feces Dufresne had to deal with, here’s how you break out of prison, with a little help of course.—PF

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28. Bane (The Dark Knight Rises)
Being that he is the hulk-sized protector to the heir of The League of Shadows alone puts Bane pretty high on the evil-doers list, but he was also the only Batman villain to ever “break The Bat.” In the end Bane fails to defeat Wayne’s brains with his brawn.—SD

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27. Sideshow Bob (The Simpsons)
Yale grad Robert Underdunk Terwilliger was destined for greater things than being Krusty the Clown’s sidekick. When he tries to achieve those things by framing Krusty for armed robbery, it’s Bart who foils his scheme. Voiced by Kelsey Grammer, Sideshow Bob repeatedly plans revenge on Bart and the rest of the Simpsons, even after starting a new life in a Tuscan village. In a series where most of the characters remain static, Sideshow Bob provides a larger arc as well as plenty of laughs.—JJ

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26. Alex (A Clockwork Orange)
The consequences of all the random acts of ultra-violence finally catch up to “Your Humble Narrator” when Alex is sentenced to prison for murder. Although the Ludovico Technique dulls his magnetic personality and robs him of his free will, Alex is the perfect anti-hero: intelligent, witty, shockingly violent, but ultimately sympathetic.—BB

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25. Narrator (“Mama Tried” by Merle Haggard)
Do you remember your 21st birthday? I’m sure it was better than being stuck in prison doing life without parole. The takeaway from this lesson in country music: Listen to your mother, she knows best.—PF

24. Roxie Hart and Velma Kelly (Chicago)
Whether they like it or not, these two musical murderesses are a package deal. Sure, real women’s prisons probably don’t allow late-night performances of the “Cell Block Tango,” but through Roxie and Velma’s story—parlaying their sins into a career as a double act—Chicago provides some commentary on the glamorization of criminals, the nature of celebrity and all that jazz.—BS

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23. Max Cady (Cape Fear)
Robert DeNiro has proven he can go to some dark places with his characters, and few are darker, or creepier, than Max Cady. Cady is out of prison for most of the film, but the scenes of his tattooed torso and disturbing collection of books and pictures inside prison are where we truly get a sense of just how demented he’s become. Once released he relentlessly, and for the most part, legally, torments the family of Sam Bowden (Nick Nolte), who went out of his way to make sure Cady served as long of a sentence as possible.—RB

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22. Sam Bell (Moon)
Nearing the end of a three-year solo operation mining helium-3 on Earth’s moon, Sam Bell comes to the realization that he is never going to be released by his captors. He’s a prisoner of convenience destined to live out his days doing the work that no one else would ever volunteer to do—imprisoned on the rock, the Alcatraz of space. But like Alcatraz, there’s always a way to escape….—SD

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21. The subjects of Sam Cooke’s “Chain Gang”
Legend has it this 1960 single was inspired by a real-life run-in with a chain-gang of prisoners working on a highway while Sam Cooke was on tour. Cooke and his brother Charles felt sympathetic towards the men, gave them a carton of cigarettes and wrote this song chronicling their hard labor.—BS

Most of us at the Paste office have already binge-watched the first season of Orange Is the New Black and enjoyed getting to know Piper, Red, Taystee and (especially) Crazy Eyes. But while we wait for their return (Netflix has yet to announce dates for Season 2), we turn our attention to some of the great pop-culture prisoners who’ve come before.

We’ve limited ourselves to one entry per book, movie, game, song, TV show, etc., so it wouldn’t just be the cast from Oz. Let us know who we missed (or if you’re feeling particular encouraging—what we got right) in the comments section below.

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20. Sgt. Hugo Stiglitz (Inglourious Basterds)
Stiglitz looks German with his short, dirty blond hair and light eyes, but these attributes hide the homicidal disposition of a revenge killer. Stabbing Nazis in the face or choking them to death by shoving his fist down their throats—the Sergeant’s only goals are to kill as many Nazis in as many creative ways as he can. Once he’s imprisoned for his actions, it’s up to the Basterds to free him and get him back on homicidal track.—SD

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19. Cpl. Nick Chevotarevich (The Deer Hunter)
Christopher Walken  took home the Oscar for Best Supporting Actor for his disturbing portrayal of a POW whose life is completely destroyed by his experiences in captivity in Vietnam. Nick is never the same after being forced to play a game of Russian roulette with his best friend, and his tragic final scenes illustrate some of the true horrors of war.—BS

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18. Lorenzo MacIntosh (“Scared Straight” on Saturday Night Live)
When you get to prison (which we hope you never do), make sure to take Lorenzo’s (Keenan Thompson) advice with slight precaution. Because according to him, it’s not at all like The Wizard of Oz. “It won’t be a lion, a tin man and a scarecrow. It’ll be you, lying down, while 10 men make you a scared ho!”—PF

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17. Snake (Escape From New York)
When the president’s Air Force One flight is hijacked and crash-lands in the now- maximum security prison of Manhattan, there’s only one man who can save him, a one-eyed Kurt Russell who goes by the name of Snake. He manages to thwart The Duke’s plans to use the President as a human shield in his march to freedom, all while maintaining his badass disdain for the US government.—SD

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16. Number Six (The Prisoner)
Timeless yet inescapably dated, The Prisoner uses the pop-culture spy craze of the Cold War as a backdrop for a philosophical battle between the individual and the collective. Trapped in a quaintly British (and extremely ‘60s) village built solely to mentally and emotionally break its captives, Number Six defiantly asserts his individuality throughout an onslaught of psychedelic mindgames from his captors. Patrick McGoohan would’ve been the best Bond, but that’s okay—Number Six’s supreme confidence and steadfast defense of his personhood makes him cooler than that horndog anyway.—GM

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15. Ryan O’Reily (Oz)
We could fill this list exclusively with characters from Oz, but if we had to pick one it’d be Ryan O’Reily. (At least it would today—ask tomorrow and maybe we’d say Adebisi or Chris Keller.) It’s not just the real-life charisma of Dean Winters (aka 30 Rock’s Dennis Duffy) that makes the thoroughly evil O’Reily so irresistible. It’s his Iago-like cleverness and his touching (if self-serving) love for his brother Cyril that turns O’Reily into a likable monster.—GM

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14. The cast of Seinfeld
You wouldn’t necessarily think that a show about nothing would wrap up with all of its lead characters in jail, but doing nothing is exactly what lands Jerry, Kramer, George and Elaine in prison as they violate a Good Samaritan law by failing to help a man being carjacked at gunpoint. It’s a goofy way to end such a long-running series, a finale that years later Seinfeld would admit on Curb Your Enthusiasm “we screwed up,” but we have to admit it’s fun to watch these characters reprise their banter about George’s shirt buttons from the pilot from a jail cell before Jerry performs one last stand-up routine clad in an orange jumpsuit, bombing in front of his fellow inmates.—BS

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13. Axel (The Walking Dead by Robert Kirkman)
He’s fine in the TV show, but we’re talking the comic version here. Axel is one of the prisoners Rick’s group finds seeking solace inside the walls that were created to keep the evil in the prison—now functioning to keep hoards of roaming killers (dead and undead) out. Despite the group’s initial hesitation to welcome Axel in, they eventually came around once he proved himself to be one of the most capable workers and defenders of their new stronghold. At least until he meets The Governor….”You follow me?”—SD

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12. John Coffey (The Green Mile)
John Coffey is a hulking, deep-voiced man who was wrongfully convicted of the murder and rape of two girls. But while Coffey was intimidating in size and build, Michael Clarke Duncan had no trouble shining an enviable understanding of the physical world across the silver screen in his lengthy conversations with Tom Hanks’ character, Paul Edgecomb. For Coffey, prison wasn’t necessarily a place that held him back. The concrete walls and iron bars instead blocked out all the hurt and evil going on outside, a mindset that would leave this Christ-like figure to a peaceful exit that wouldn’t allow for a dry eye in the theater.—TK

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11. Junior Soprano (The Sopranos)
When his Uncle Junior goes down on some federal racketeering charges, our favorite antihero Tony Soprano gets promoted to acting boss of the family, setting up five more seasons of some of the best drama TV has ever seen. Health issues allow Junior to serve out his sentence under house arrest, where he often provides some of the series’ comic relief; once a ruthless mafia captain, he’s now a cranky, confused old man wholly dependent on others.—BS

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10. Ulysses Everett McGill, Pete Hogwallop and Delmar O’Donnell (O Brother Where Art Thou?)
After escaping from a chain-gang while still chained together, this trio sets out on an epic journey—a clever adaptation of Homer’s The Odyssey, in fact—to find the $1.2 million in buried treasure that self-appointed leader Everett (George Clooney at perhaps his most charming), “the one with the capacity for abstract thought,” insists he hid before his imprisonment. He’s the vehicle for that classic Coen Brothers wit, able to talk himself out of most any situation, and Pete and Delmar serve as his hilariously dim foils; their travels include all the highlights from the Greek poem and even a hit single as The Soggy Bottom Boys: “Man of Constant Sorrow.”—BS

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9. McMurphy (One Flew Over the Cuckoo’s Nest)
If you’re already calling B.S. on this pick, hear us out. While R.P. McMurphy pushed for a stay at an Oregon psychiatric hospital in lieu of a prison sentence for statutory rape, the confines are pretty similar—if not worse—for this repeat menace to society. Hell, even when McMurphy was “in the cooler one September they let us bring in a TV and watch the Series.” While a mental institution might have seemed like a cakewalk for McMurphy on paper, its rigid guidelines, toxic head nurses and the banality of the whole thing would lead to his downfall—and prove to be much more than he could have expected to deal with. Here, we see a character brimming with life punished and beaten into mediocrity. And when Nurse Ratched charges McMurphy with his own personal, worst-case prison sentence, a friend he’s made in the long-term comes to bail this jailbird out one last time.—TK

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8. Jake and Elwood Blues (The Blues Brothers)
They don’t call him “Joliet Jake” for nothing: when we first meet John Belushi’s character in The Blues Brothers, he’s being released from Joliet Prison and picked up in an old cop car by his brother Elwood, who promptly informs him of his plans to get the band back together. By the end of the movie though—after they’ve completed their “mission from God” and concluded one of the best chase scenes in movie history—the whole gang is back in the slammer, where thankfully, they’ve got access to a stage and a little help from James Brown, Aretha Franklin, Cab Calloway and Ray Charles for one final performance of “Jailhouse Rock.”—BS

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7. Sirius Black (Harry Potter and the Prisoner of Azkaban by J.K. Rowling)
Sirius Black helped transform the Harry Potter series from kids’ books to that rare saga that anyone could—and did—enjoy. The escaped Prisoner of Azkaban loomed as a shadowy villain throughout most of the third book—Harry’s godfather who betrayed his parents and was returning to finish the job. What he would become was much more complicated, a once-carefree spirit damaged by 12 years with dementors.—JJ

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6. H.I. McDunnough (Raising Arizona)
Nicolas Cage’s H.I. McDunnough seems to have resigned himself to life as an on-again-off-again jailbird until he falls in love with the prison’s mugshot photographer, played by Holly Hunter. McDunnough is released, the two get married and he cleans up his act. When they’re unable to have a child, however, they decide to steal one from a couple that had quintuplets. Raising a child proves more cumbersome than the couple expected, especially when McDunnough’s convict friends escape from jail and expect to stay with the new family. Complications, realizations and trademark Coen Brothers hilarity ensue.—RB

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5. Narrator (“Folsom Prison Blues” by Johnny Cash)
It’s rare that we can feel so much empathy with someone who “shot a man in Reno, just to watch him die,” but his resigned sadness in lines like “When I hear that whistle blowing, I hang my head and cry” make you miss the sunshine right along with him. That Cash performed and recorded the song at Folsom Prison just makes it that much more poignant.—JJ

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4. Hannibal Lecter (Silence of the Lambs)
Hannibal “the Cannibal” Lecter is maybe one of the few characters out there who doesn’t make us sleep any easier by living behind bars. The character—most famously played by Anthony Hopkins—blends intellect with his intimidating presence to justify precautions like that terrifying signature face mask. Through Silence of the Lambs, his prison break seems inevitable, but the more disturbing thought is that he’s sticking around to play his twisted game with Starling.—TK

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3. George Bluth (Arrested Development)
The Bluth family patriarch’s arrest for defrauding investors, grand theft, petty theft and some “light treason” was a big deal; it forced his son Michael to take over the company and keep everything together, and it taught everyone important prison lessons like NO TOUCHING! and that they don’t allow you to have bees in here. But—much to our delight—George Sr. made the most of his time in the clink, recording his “Caged Wisdom” tapes and even plotting a few semi-successful escapes.—BS

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2. Luke (Cool Hand Luke)
After a cop catches him cutting of the tops of parking meters, Paul Newman’s Luke is sent to prison, where his individuality and relentless anti-authoritarianism slowly earn him the respect of his fellow inmates. He becomes a Christ-like figure, continually sacrificing himself to show the other prisoners that though they are incarcerated, they are slaves to no man. (It’s no coincidence that Luke eventually meets his demise in a church after he escapes.) Though Luke is killed, what’s important is that the previously impenetrable sunglasses of the Captain are crushed as the car containing his dying body pulls away.—RB

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1. Andy Dufresne (The Shawshank Redemption)
The hero of Shawshank Prison is the only inmate on our list who crawled through a river of shit and came out clean on the other side. A small piece of advice from Dufresne to his fellow prisoners can go a long way: “Get busy living, or get busy dying.”—PF

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