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.

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

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

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

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

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

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.

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

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

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

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

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.

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

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

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

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

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

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

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

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

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