Cardboard Prison



"In the big rock-candy mountain all the jails are made of tin, And you can walk right out again as soon as you are in"

- Various artists, most famously Harry McClintock for O Brother, Where Art Thou?, "Big Rock Candy Mountain"

In the spirit of Joker Immunity, the judicial incarceration system is worthless. It may keep certain villains off the street so that the heroes just have to deal with one at a time (except for those "teaming up" deals), but expect them to bust out real soon or find a very sympathetic parole board.

In the real world, voters would be demanding crackdowns. In fictionland, the same person can break out hundreds of times and nobody gets fired. In some cases, they also have policies against re-arresting escaped Villains Out Shopping unless they commit another crime during the same episode.

Perhaps a necessity in stories which feature a Rogues Gallery, since you need to find a way to keep bringing them back but have the heroes seem somewhat effectual. This was particularly true in comics in the days when the Comics Code held sway—the villain had to be clearly defeated at the end of each and every appearance, requiring an escape from either incarceration or apparent death before he could show up to vex the heroes again.

In some cases, a Cardboard Prison can also serve as an Tailor-Made Prison that's just waiting to be opened.

Also known as Houdini's Postulate.

Contrast with Luxury Prison Suite (in which the character might not want to leave prison, because of how nice it is), Might as Well Not Be in Prison At All (in which the character doesn't have to leave the prison to remain a threat), and Play-Along Prisoner (in which the character doesn't currently want to leave the prison, but could if they did). Also contrast The Alcatraz, which actually is hard to escape from, but possible—see Great Escape. This problem is frequently solved via Self-Disposing Villain, and the occasional Heel Face Turn.

See also Unsafe Haven, where instead of a prison being laughably easy to break out, a sanctuary is laughably easy to break in.

Anime & Manga

 * Minor villain Beck from The Big O breaks out of prison no fewer than three times over the course of the series, although sometimes he has help.
 * Both Lucia and Gale (King) Raregroove broke out of a prison at some point in Rave Master. King escaping a regular jail only three days after being locked up so he could get back at the other Gale. Lucia busts apart a maximum security prison (it's implied that he broke a several feet thick metal wall with his bare hands-he's just that Badass) ten years later, waiting that long only because he had nothing better to do for that stretch of time.
 * Done with Axis Powers Hetalia, where Germany can dig his way out of a prison. England also manages to escape from prison because his Italian guards don't pay attention, but he always gets dragged back by Germany.
 * The Mari Land prison in Onegai My Melody: Kuromi and Baku can escape with minimal efforts. Repeatedly.

Board Games

 * Monopoly features one of these with its jail. To get out, you only have to pay $50, roll doubles, use your "Get Out of Jail Free" Card, or just wait three turns. It somewhat subverts this trope as well, because since you can't move around the board landing on expensive rival-owned properties, jail is actually the best place to be.
 * Depending on personal degree of cynicism, the $50 is either paying the fine, or paying the bribe.

Comics

 * One of the classics is Arkham Asylum from Batman, although this was lampshaded a few times in the comics (e.g., as the effect of a curse). Not only is Arkham Asylum worthless, it seems to make its inmates worse instead of better. (Of course. What did you expect? It's ARKHAM! Cue insane laughter.)
 * One of the funniest lampshade hangings on this was in the The Sandman, when a villain locked in Arkham learns that someone else intends to escape, and on a whim, with no planning at all, escapes as well.
 * Oh, that's nothing. In issue number two of The Joker's own comic book, a pair of bumbling Arkham security guards are fired because The Joker has escaped on their watch five times. And keep in mind: this series was published in the mid-seventies. You know it's bad when people have lampshaded Arkham's poor security for thirty-odd years.
 * One comic mentioned that Batman is a bit rougher with his more dangerous enemies than is strictly necessary to subdue them for precisely this reason. If he simply puts the Joker in Arkham, he escapes. If he puts the Joker in Arkham with a couple of broken bones he will take the time to convalesce before escaping. Usually.
 * Gotham City also has Blackgate Penitentiary for its non-insane criminals. It's just as bad as Arkham.
 * After becoming a Reality Warper in the Emperor Joker storyline, the Joker is sent to a real prison, Slabside Penitentiary, which is nicknamed "the Slab". Supposedly, no villain has ever broken out of it. In Joker: Last Laugh, the Joker is informed that he has terminal cancer. It takes him all of about five minutes to think up a plan to not only break himself out, but break out most of the other villains with him, and use the prison's own anti-riot countermeasures to "Jokerize" them all. Maybe The DCU's prisons aren't cardboard prisons. Maybe the Joker is just that good.
 * The two aren't mutually exclusive.
 * Surprisingly averted in both modern Batman film series. While Arkham Asylum is practically the Trope Namer in any other medium version of the story, the film versions tend to keep things nice and tight for the most part, with even supervillains staying locked up. Even the mass breakout in Batman Begins occurs due to the outside influence of the organisation that runs the place (essentially, they cause their own breakout).
 * Meanwhile, The Joker Blogs (a fan-created "sequel" to The Dark Knight) demonstrates what would make a prison cardboard. Not only is the Arkham staff as corrupt as the Gotham police force, but Mr. J is just that intimidating and effective, with those helping him either genuinely believing it is in their better interests or just as twisted in their own ways.
 * Lampshaded in one Superman novel, in which Luthor is sent to prison. Jimmy Olsen immediately starts writing his report about Luthor's escape, before he had actually done it. In the course of the story Olsen mentions that following one previous escape, Luthor had later broken back into the prison to retrieve something he had inadvertently left behind, then escaped again.
 * Generally averted, or at least justified in Knightfall where Bane attacks Arkham with the arsenal of a small country to break it open.
 * Intermittently, The DCU attempts a solution to both the in-character problem of Cardboard Prisons and the metafictional problem of keeping losing villains effective, by having villains perform missions as part of the US government top-secret Task Force X, a.k.a. Suicide Squad. This program offers early releases for imprisoned supervillains if they participate in, and survive, extremely dangerous secret missions that are subject to official denial. Thus, the villains temporarily become Anti-Hero protagonists.
 * Justified in the case of The Flash's Rogues Gallery by the fact that one of them can travel to an alternate dimension and back via mirror. Every time the Flash arrests any of his friends, Mirror Master goes and fetches them right back out again. The warden explains that they've tried to have the mirrors removed but prisoner-rights liberals won't have it.
 * There was also the time Abra Kadabra got out because he was allowed to work in the kitchen and somehow formed the equipment there into a hypno-ray. No, really.
 * And then there's Dr. Alchemy, who uses prison for reading time and when he finishes a book, he turns the walls into oxygen and walks out... only to walk back in a month later with a new stack of books.
 * "The Vault" was the Marvel Universe's most secure prison, but it was still a Cardboard Prison, with pretty much any villain escaping as needed for various comic book plots. Its cardboard nature was actually commented on by writer Kurt Busiek, as the reason the writers had it destroyed. After its destruction and the resulting mass escape (the final shredding of the cardboard, if you will), supercriminals were incarcerated in lesser prisons nationwide, with predictable results.
 * Subverted in the alternate reality, Punisher Kills The Marvel Universe, where Punisher kills most if not all of the Vault's inmates by teleporting a giant flood inside the prison.
 * The Vault has now been replaced by the Raft. It was first introduced in the first arc of New Avengers. Said arc is about a massive jail break.
 * "Prison 42", nicknamed "Fantasy Island" by its inmates, debuted in Civil War. It's located in another dimension, accessible only by certain teleporter systems, secure and heavily coded. Many superheroes unwilling to register with the government were locked up there, and were indeed its first inmates. It was supposed to be the final answer to the Cardboard Prison. Naturally, the anti-registration heroes on the outside engineered a mass jailbreak...
 * To be fair, many remained there after that and were only freed when Blaastar invaded.
 * Likewise it serves to be a sort of Deconstruction of what steps you would have to take to actually make a prison immune to the kind of crazy shit filling the Marvel Universe.
 * The prisons of the Lucky Luke comic. This is subjected to frequent Lampshade Hanging.
 * The first time in DC Comics that the Crime Syndicate of Earth 3 showed up, they were beaten and imprisoned in a bubble created by Green Lantern, and THEN thrown into a limbo between dimensions/earths. They kept somehow breaking out and causing trouble.
 * Not that often and, at least the first time, only after outside interference. Johnny Quick, Power Ring, and Superwoman managed to escape from the bubble after an interdimensional traveler passed by and somehow weakened it (no real details given). That was about 14 years after their first appearance (real time; in comic time, it could have been anything from a week and a half later). A couple of years later, Ultraman got out, but nothing at all was said about how. Owlman wasn't seen again until the Crisis, and could well have been stuck in the bubble the whole time until the entire Syndicate returned home in time to die in the destruction of Earth-3.
 * French comic book Le Mercenaire contains a literal example of a cardboard cell. The hero is imprisoned inside a flying castle, which is in fact a giant hot-air balloon. Hence, everything is constructed of light and hollow material, including the large jar used as cell, which is thick cardboard. The prisoner was relieved of any item that could pierce it beforehand (including his belt buckle), but can cut through once he receives exterior help (in the from of dagger).
 * Justified in the case of The Silver Age of Comic Books Mad Scientist version of Lex Luthor, who was fond of MacGyvering a Phlebotinum-powered escape device out of absolutely anything. Writer Elliot S! Maggin once had Luthor muse that it had reached the point where the only two items his guards would allow him to have were a pen and a pad of paper. Luthor had, in fact, long since figured out a way to turn the ink, metal, plastic, and wood pulp into a high explosive to blast his way out, but he would never do so, because then the next time Superman threw him in prison, the prison wouldn't let him have a pen and paper any more.
 * We can't forget the time he built a radio to the future and was able to engineer an escape. By calling supervillains in the future. Yes.
 * One Golden Age Captain Marvel comic has his bald Mad Scientist adversary, Dr. Sivana, sitting in prison grumbling that there's no point in escaping because Captain Marvel will only catch him again. He then thinks up a plan to destroy Captain Marvel and, his mood brightened, easily escapes by simply performing a mathematical calculation in his head that "opens a portal to the fifth dimension" and then walks out through a wall like a ghost.
 * In Justice League of America #5 Monty Moran 'the Getaway Mastermind' breaks himself and 5 other supervillains out using a shrinking ray he somehow built that makes them half an inch tall. Then they use a balloon with a container underneath to get out.
 * It is slightly better in Strange Tales #105 where the Wizard becomes a trustee, makes a formula that eats through stone from chemicals in the Medical area, then hides in his cell while the guards rush through leaving the door open.
 * It gets more ridiculous in #118 where he knocks out a guard with gas he made after luring him inside his cell by crying for help, disguises himself as him using melted crayons to cover his beard, then uses an anti-gravity device he wears to escape.
 * Dilbert has a similar situation to The Simpsons example below, when Wally is imprisoned, and Dogbert tells him that the guards just pretend to lock it up. As Wally said, "I'd have to say, the lifers were the most embarrassed."
 * Another occurrence in the same comic: the PHB is sent to do time in a place so horrible it has no name—Wally's cubicle—which has no door at all (the PHB serves his term because his sense of direction is so poor he cannot find the way out again).
 * The Beagle Boys (Disney Ducks Comic Universe) use prisons as a temporary home, and are known to jailbreak at any convenient moment. A recurring gag is that they receive a cake filled with tools; once, the cake was the tool, as it was so dense and heavy that it could be used to smash the pavement, and the frosting used to dig.
 * The Punisher occasionally finds himself thrown in jail, but it's usually part of a Batman Gambit to kill a crime lord who's already behind bars in the same prison (for example: the final level of the video game). One time Daredevil, Spider-Man, and Wolverine all teamed up in an attempt to stop the Punisher once and for all, but at the end of the battle the Punisher points out that if they put him in jail he'll just kill every inmate in the prison before escaping again. The three heroes agree and let him go.
 * Averted in DC's Flashpoint Universe where supervillains commonly get the death penalty and the prisons are guarded by Amazo robots who absorb the powers of the supervillain inmates. But villains still escape.
 * Mostly averted with the now-defunct Stormwatch, who under Henry Bendix's leadership placed supervillains in cryogenic prison without trial.
 * The absence of these is actually a plot point in Watchmen. Because all the supervillains the Minutemen thwarted tended to stay thwarted, they eventually ran out of situations that required a team of heroes to deal with. This was one of the factors that led to the Minutemen breaking up.
 * Any time Popeye goes to jail, this trope goes into effect as Popeye uses his strength to take the wall of his cell apart brick by brick. In one early strip he was kicked out of jail for doing this!
 * In a comic based on Batman Beyond featured on Scans Daily the Royal Flush Gang are out committing crimes when they are supposed to be in prison. Terry doesn't know how they could have escaped noting, "This place is locked up tighter than a drum." Despite the outcome, Terry's comment still seems like an odd thing to say when Bruce Wayne has told you all about his past, with one person posting, "Uhh, Terry? You got in, didn't ya?"
 * In an subversion in the Marvel Universe, the Absorbing Man was once literally placed in an cardboard box in a prison cell because it was deemed the only way to hold him in prison since he takes on the nature of any matter he touches. Unfortunately, there is a water pipe leak which dripped on to the box, allowing him to take on the nature of the water and then use that form to reach the brick and iron work of the cell, change into that material and smash his way out.
 * Any prison is this for Diabolik. The first time he had been arrested (alluded in his first story and shown in a flashback years later) it had been because his perfect masks weren't known yet, so the police didn't realize he was wearing one and he walked out of a maximum security prison with a stolen guard uniform after taking the mask off, but later imprisonements, happened after his masks and real face were known, all ended with him breaking out rather easily in spite of always increasing measures to keep him long enough to execute him, with a Jerkass Victim getting executed in his place once.

Fan Works

 * In the Teen Titans fanfic Joker's Wild, they give the explanation that the state of Jersey gives Arkham a huge defense budget, but forces them to spend it all on security equipment, and can barely afford the little staff they have. People escape so often because the secretaries and janitors are payed so little they are easy as hell to bribe.
 * All too much, to be honest. Most escapes from such facilities in Real Life are inside jobs for a reason.
 * Snap and Loopin in My Immortal are constantly send to St. Mango's or Azkaban, but are usually found somewhere around the school by the next chapter. It's mentioned that Britney had helped them escape once.
 * Arnold in soulless shell manages to talk his guards into helping him escape and joining him to fight against Leif.

Films -- Animation

 * In Megamind, the title character can apparently escape the prison with ease, as long as he has help from Minion.

Films -- Live-Action

 * Hilariously spoofed in Support Your Local Sheriff. James Garner finds himself trying to hold frontier thug Bruce Dern in a jail with no bars—they have been ordered but haven't arrived yet on the stage. He draws the door and bars on with chalk and tells Dern that he is on the honor system. However, he enforces the honor system by being effortlessly smarter than his buffoonish prisoner and appearing in front of him with a gun whenever he tries to sneak out of the jail.
 * It wasn't just a chalk-line; he also used some dribbled red paint and applied psychology. Dern's character is relieved when the bars finally arrive, and helps install them.
 * In Public Enemies John Dilinger twice escapes prison the same day he is admitted, and fully expects to every time he faces the possibility of arrest.
 * Cool Hand Luke's title character is able to escape prison regularly (though he's usually brought back quickly). Finally, the sheriff has enough and shoots him.
 * Hancock cannot be held by any normal prison due to his powers; his willingness to stay in one is part of his Character Development.
 * In Law Abiding Citizen, protagonist Clyde Shelton (Gerard Butler) checks in and out of a so-called maximum security prison through.
 * The resident superhero in Mystery Men (a spoof of superhero movies) gets tired of catching thugs, having caught all the supervillains long ago, and uses his influence to get the parole board to release one of his former enemies from an institution for the criminally insane. However, he underestimates his foe, is captured, and subsequently ends up dead. Inverted in that the parole board didn't buy the villain's "cured" act for a second until the intervention of the hero.
 * In the remake of Three Ten to Yuma, the prison train fits this trope. It is established late in the film that wanted gang leader Ben Wade (Russell Crowe) has already escaped from the prison train to Yuma at least twice before the events of the movie. After, Wade willingly steps onto the train and sets off on his trip towards the prison—but not before he calls his faithful horse to ride alongside the train, proving that as soon as the film ends, he'll simply escape again, rendering the whole film pointless.
 * In Species, the alien/human monster is grown in a cage. Between her and freedom: a glass window, an unlocked door with a crash bar (no pesky knobs to turn), and a chain link fence.
 * In The Flintstones: Viva Rock Vegas, while in prison, Barney realized he can slip through the bars to steal the guard's keys and get Fred out too.
 * In X 2 X Men United, Magneto literally smashes his way out of prison the second he gets his hands on some metal. It's also worth noting that the method he and Mystique used to get the metal into his cell in the first place was one they could have used basically whenever they felt like it, so presumably they had already worked out the plan so that as soon as Mystique was able to find out where his prison was (and the name of a guard working there) they were ready to go.
 * In Cube there is a character nicknamed The Wren who has escaped prison 6 times. Sadly, he's not so lucky in the Cube.
 * The two prisons shown in Austin Powers: Goldmember. The first one is a Swiss maximum security prison, where Doctor Evil is placed in a transparent cell in the middle of a big room, surrounded by armed guards round-the-clock. Then Dr. Evil accidentally pushes open the door to his cell. No alarms sound. He waits a second, then says "I'll get it", and closes the door. The second prison is in the US, where Dr. Evil and Mini-Me escape after starting a prison riot, despite floodlights aimed at them along the wall. Of course, the whole thing is played for laughs.
 * In The Smurfs, Gargamel accidentally summons a swarm of flies to escape Rikers Island in New York City.
 * Played for laughs in Idiocracy, where everyone in the future is an idiot. The hero escapes jail by telling the guards that he's supposed to be let out, and they believe him.

Literature

 * Azkaban in Harry Potter is a Tailor-Made Prison in all but name, but escape seems to be a simple affair, with Sirius Black and Barty Crouch Jr. escaping relatively easily (though granted they had respectively), and becomes really cardboard when the Dementors (who are supposed to be guarding the place) start helping the inmates escape.
 * Justified in Dave Barry's novel Big Trouble, where the contractor for a prison security system is better at bribing public officials than at designing prison doors that don't open automatically during a severe thunderstorm. The contractor is also good at finding scapegoats for massive prison breaks.
 * In the Discworld novel The Last Continent, Rincewind finds himself imprisoned in a jail cell on the continent of XXXX, awaiting execution. The guards inform him that the cell's previous inhabitant, "Tinhead Ned", used to escape with regularity. Rincewind dismisses this as an attempt to break his spirit by getting him to run around rattling bars and searching for hidden panels. Then he finds a message from Ned, telling him to "check the hinges". He discovers that the cell's door can be entirely removed with sufficient effort, and escapes. At the end of the novel, after becoming a national hero, he requests that the cell never be redecorated, thus assuring that it will retain its cardboard nature for the next person to wind up inside it.
 * A couple of other 'prisons' prove to be equally or even less effective. The prison at the Patrician's Palace doesn't keep said Patrician in for any longer than he wants it to (although he designed it to be so), the room a pack of Werewolves lock Sybil in in The Fifth Elephant doesn't hold her any time at all, although its failing are due to the fact that non-dungeon rooms in a castle are generally not good at keeping people in. Mostly subverted otherwise though, most prisons are pretty effective, with escapes relying on outside intervention, like a zombie tearing the wall down.
 * In David Weber's Honor Harrington series, the government of Silesia is so corrupt that most of the authorities are, individually, in cahoots with one or another band of pirates in the area, and frequently find excuses to release them when they're caught by Manticoran patrol ships. This leads to the Royal Manticoran Navy's draconian policy: Anyone caught a second time engaging in piracy will be executed immediately.
 * In Fingerprints, a heavily drugged prisoner manages to just wander out during a computer malfunction. Yes, it was a makeshift prison being maintained by just one person, but still: epic failure.
 * Subverted Trope partially in "The Problem of Cell 13". Professor Augustus S. F. X. Van Dusen, The Thinking Machine, (a man who makes Sherlock Holmes look like a backwards nursery tot) has himself locked in the death cell of the local prison with the condition that he must escape in one week with only the things an actual condemned prisoner would have in order to prove a point to some other scientists. Van Dusen notes that the prison is very admirably administered, but still escapes via Awesomeness By Analysis.
 * Specifically, Van Dusen asks for three things: tooth powder, a small amount of money, and a shoeshine. All three serve a function in his escape plan; of them, the only thing the prison administrator hesitates on is the money, but finally decides it's too small a sum for Van Dusen to bribe a guard with.
 * Subverted Trope in Alcatraz Versus the Evil Librarians, which has many elements of an Affectionate Parody of fantasy-adventures. The cell Alcatraz and his team are locked in is quite immune to Smedry Talents. Fortunately for our heroes, the Evil Librarians didn't take nearly as great precautions when assigning the guard.
 * In the second book in the Shadowleague trilogy, Cergorn decides to imprison Veldan and Kazairl. In their house. Guarded by their friends. It wasn't his day.
 * In one of Enid Blyton's Magical Faraway Tree books, a character is put in jail in The Land of Goodies for eating part of someone's house (which is made out of sweets). Predictably, he just eats his way out of the prison.
 * In Holes, Camp Greenlake has no fences, guards, attack dogs, etc, so it's very easy to run away. The reason nobody does so is because there's nothing but desert all around, and the camp is the only place with water.

Live-Action TV
"The Master: Brigadier, if I wanted to break out, I wouldn't still be here."
 * In the eighth season of Doctor Who the Master is finally caught by UNIT. They make a big deal about how this evil-doer has finally been caught, and led away in handcuffs. Three adventures into Season 9, the only reason he's still in the prison is that he's taken it over and turned it into his secret base.
 * Lampshaded in the novel The Face of the Enemy.

"Guard: [on the phone to his superiors] You'd better get down here, sir, she's doing it again. Dr. Song, she's... packing."
 * Subverted in the novel Seeing I: The Doctor becomes incredibly frustrated trying (and repeatedly failing) to escape from a supposedly minimum-security prison, because he can normally escape from even the most secure prisons within a few hours.
 * River Song's incarceration in the Stormcage Facility is completely voluntary on her part. Whenever she finds out that the Doctor needs her for something (whether it's the end of the world or just a nice party), it takes all of twenty minute for her to get out. What's more, when she's done helping the Doctor, she voluntarily returns to her prison. Of course, it might just be because she's just that good at breaking out.


 * In "A Good Man Goes to War", she picks up one of the security phones and tells them to turn the alarms off, because she's breaking back in this time. So they do. Then she orders breakfast.
 * Parodied in the Ripping Yarns episode "Escape from Stalag Luft 112B", in which Major Phipps becomes the only man never to have escaped from the prison camp of the title.
 * The Andy Griffith Show plays this for comedy with Mayberry's jail. The Sheriff keeps the keys on a hook next to the door so that the town drunk can lock himself up at night and let himself out in the morning.
 * This is yet another aspect of Nazi incompetence in Hogan's Heroes. Not only is Stalag 13 so cardboard that it's a waypost for other escaped prisoners and underground agents, the number of escapees that come through suggest that the other Stalags aren't much better.
 * The prison Faith is kept in on Angel is presumably sufficient to keep ordinary humans inside. However, after Faith breaks out of it in 30 seconds (including about 1 second of planning), there can be no question that her incarceration was completely voluntary.
 * Parodied in a sketch on The State, where the warden informs the prisoners that the only two ways of escaping Lowell Maximum Security Prison are either "dead in a pine box" or "that big, wide open gate over there... let's consider the open gate (air quotes) off limits." One prisoner decides to escape while the guards aren't looking, but ends up feeling so guilty about it 5 years later that he comes back. So the warden decides to increase security by setting up orange cones that spell "OFF LIMITS" in front of the gate.
 * The Supermax facility where Neal Caffrey is held during the White Collar pilot is managed in such a way that ordering a guard's uniform online and having it shipped to oneself at the prison is a viable escape plan. Clearly the staff don't monitor prisoners' internet access or screen their mail for contraband. On top of that, the guards fail to recognize a prisoner because he just shaved off his beard.
 * Anytime the good guys are imprisoned in any incarnation of Star Trek, it's pretty much expected that they will escape by the end of the episode. For some reason, aliens think that exposed circuits and electronic doors that have control panels on the inside are strong security measures.
 * Not to mention how the prison doors are Force Field Doors... They run on good old-fashioned energy conduits, which stops working as soon as there is a power outage.
 * Parodied in Lie to Me. Lightman manages to slip right out the door of an asylum in his typical audacious fashion. Five seconds later, he gets dragged back inside by two annoyed orderlies.
 * Supernatural portrays Hell as rather ineffective at containing demons. Demons who are exorcised back to Hell pop back up to cause trouble again at the Speed of Plot (e.g. Meg, Ruby, Alastair, Lilith). Considering who is in charge down there, this is probably deliberate. Lucifer's cage also qualifies if you take his army of fanatically loyal minions into account. Combinatorial calculations yield at least 1.22 x 1087 distinct methods by which he could be freed. (This figure assumes that there are exactly 600 seals, that the first and last seal are fixed, and that breaking the same seals in a different order doesn't count as different.) On top of that, the actual seals include things like a "righteous man" (read "Dean Winchester") shedding blood in Hell in a canon where Being Tortured Makes You Evil and one of the aforementioned fanatically loyal minions sacrificing herself for the cause. Accordingly, springing Lucifer is as easy as baby kitten pie. Again, given who is in charge of the imprisonment, this is deliberate.
 * The Hazzard County Jail from The Dukes of Hazzard. Even if the Duke boys do manage to get themselves locked up, they usually manage to get themselves out within minutes.
 * On The A-Team, no mental institution could ever seem to hold Murdock if his teammates wanted to break him out.
 * On Heroes, D.L.'s ability to phase through any surface means that he can escape through any facility; he even tells his son that no prison can contain him.
 * In an episode of Hercules: The Legendary Journeys, Hercules is arrested, but he only stays of his own free will. When a villain starts attacking the city, Hercules punches a hole in his cell wall, gets out, stops him, and comes back.
 * In a later episode of Arrested Development, GOB is imprisoned, but the guards keep poor protection of him. They leave the keys in the cell and even leave the cell door open. It is inverted because he does not even try to escape he throws the keys back and closes the cell door and he then mocks their stupidity. It is justified, however, because they wanted him to escape so they could follow him and see if he was up to something.
 * Scorpius is kept in one during his time on Moya in season 4 of Farscape. When the others finally realize that he could have escaped any time he wanted, he uses his voluntary incarceration as evidence that they should trust him.

Music

 * As mentioned in the page quote, Big Rock Candy Mountain describes jails made of tin sheet metal, something the common man could tear down (if not punch right through) barehanded.

Radio

 * The Goon Show episode "Tales of Old Dartmoor" involves the inmates of Dartmoor Prison escaping but taking the prison with them, leaving a literal cardboard replica in its place.

Tabletop Games

 * This sometimes comes up as a reason why characters in Dungeons & Dragons end up killing the Big Bad of a story rather than capturing him (even if he surrenders). Locking the bad guys up in prison just gives the Game Master an excuse to have them break out to menace the party again at the least convenient time.
 * Of course, since many RPGs have a canon method to resurrect people, killing a BBEG just serves as an opportunity to give the BBEG an undead or demonic template.
 * Meanwhile, imprisoning the heroes seldom works any better. A number of adventures even start with the heroes locked up, operating on the assumption that they'll escape.
 * Warhammer 40,000, being WH40K, some stories play this painfully straight, while others subvert it so hard it isn't funny. In the story Dark Apostate, the villain protagonist escapes with ridiculous ease from a Dark Eldar prison within six hours of arriving (while holding in his intestines with one hand), while another tale tells of a prison on a death world called Phyrr where everything is toxic, including the spores which infest the air. Should the prisoners ever riot, the orbiting control station just opens all of the doors, and lets everything inside.
 * The second Eisenhorn novel is an interesting example, because it changes depending on perspective. The title character is incarcerated in the most secure prison in the second most fortified planet in the galaxy, and is still freed in a matter of hours after his allies implement their plan. However, he was in the prison for about three months, and it is entirely plausible that they spent all of that time planning and simply decided it was safer not to tell him.
 * Very much the case in the Freedom City setting for Mutants and Masterminds; the character most focused on making it un-cardboard is the Warden, and he's a dangerously unstable Knight Templar.

Video Games
""Officer, do you really think my client is capable of these acts?""
 * In Batman: Arkham Asylum, the intro takes pains to show off Arkham's new "improved" security system. It takes all of 10 minutes for the Joker to not only break his bonds, but take over the asylum and free all of the inmates. In fairness to the Arkham staff, a good bit of work had already been done for him. He arranged a fire at the Gotham prison to get his mooks on the island, and Harley already had control over the security system.
 * The general majority of prisons in Rockstar games, prominently Bully and the Grand Theft Auto franchise, are this. You get caught for [INSERT HEINOUS CRIME HERE] and your punishment? They take away a bit of cash and some easily replaced weapons.
 * It's assumed (or rather, explicitly stated) that the Liberty City/Vice City/San Andreas/other location police are very, very corrupt (which is actually part of the plot of San Andreas). The money they take is a bribe.
 * That said, in Vice City, having a lawyer as a friend doesn't do Tommy any harm at all.

"Native: The only thing confounding us more than how you keep escaping is why you keep coming back."
 * Zigursky Prison, also known as "The Zig", in the MMORPG City of Heroes. Its walls are so permeable that bands of escaped prisoners freely roam the streets of Brickstown, the zone in which it is located—not to mention all the bosses and archvillains who take advantage of its apparent revolving-door policies. The tutorial in the counterpart City of Villains has your character escaping the Zig as part of a massive prison break.
 * Also, some mission maps contain prison areas where your character goes if defeated. When you wake up, all that stands between you and freedom are some guards and a door that can't take more than a few good shots from whatever powers you have.
 * An extreme example of this is the final mission of the "Faultine" series: between when you get the MacGuffin and when you get the mission to destroy it (about 30 seconds), the villain you defeated to get it escapes from the Zig.
 * Parodied in Toonstruck. The guard has a sensitive nose that can be irritated by dust from your cell's doormat, incapacitating him. If you're locked up again, he acquires a gas mask which you persuade him to take off. If you're locked up again, the guard has quit in disgust, leaving a note that the key is under the mat.
 * You're thrown into a prison hut at one point in The Secret of Monkey Island. The natives (who imprisoned you) go through more and more elaborate door security systems if you keep getting captured. Of course, they never notice the Guybrush-sized hole in the floor...


 * Prisons in Monkey Island games are never renowned for their security, but the prize must go to the Flotsam Island Jail in Chapter 4 of Tales of Monkey Island: to get out, Guybrush simply says he wants to see his lawyer—which happens to be Guybrush himself.
 * This same example also simultaneously subverts the trope. You can tell the guard to go get some food for you, then try to take advantage of a loose window bar (which turns out to be a bit less loose than it seems at first) or a soft spot in the wall (with solid steel directly underneath).
 * In Chapter 5,
 * The keys to the Phatt City Jail in Monkey Island 2 Le Chucks Revenge are just outside the cell, being guarded by a dog. If I remember correctly, you distract the dog with a bone to get him to drop the keys.
 * Subverted slightly in The Legend of Zelda Ocarina of Time. Every time Link breaks out of his cell and the Gerudo guards see him, he's captured again and thrown back in. Of course, it doesn't occur to anyone that, since he keeps getting out of prison, they might want to put him in a different cell.
 * Or take away his items...
 * This happens again in Windwaker. The difference is that this Link only has a wooden shield on him at the time.
 * In Maniac Mansion, your characters get thrown in the basement dungeon when they are captured by the family. However, all it takes to get out is for one person to push on a brick while the other walks out, so the prison can hold only one character at a time.
 * Or no characters, if you take the time to acquire the cell door key from the living room chandelier. Which the Edisons never confiscate from you.
 * Chrono Trigger. You break out of the slammer twice. And only the later (earlier?) one has them bothering to take your weapons. Why this makes the characters incapable of casting magic, I'm not sure.
 * Mildly averted in Mega Man 6, the only game where Wily doesn't escape or "reform" has Wily go to prison and he stays in there for several months before escaping due to riot caused by his robots.
 * Mega Man 7 reveals all of the robot masters defeated by Mega Man are put in a museum with minimal security. Of course Wily manages to break in, thankfully however he only manages to take Guts Man.
 * In Metal Gear Solid 3: Snake Eater you break out of not just a jail cell, but an entire military base with only 1 eye, no clothes, a fork, a Single Action Army with no ammo, and some rations.
 * Made a great deal less impressive by how your cell guard is an ancestor of Johnny Sasaki.
 * In Tales of Symphonia, you break out of several prison cells. One early in the game by shooting the guard with the Sorcerer's Ring (which your captors didn't take for some reason). Again
 * Escaping from Plain Rock Asylum in XIII takes, ooh, half an hour.
 * Champions Online has the prison in the West Side in Millennium City. It's an ongoing "Open Mission", where the player can join at any time during the plot. Impressively, the building has a realistic scale.
 * Subverted in the Desert area, with the Stronghold, a prison for super-criminals. Yes, there's a breakout, with a lot of super-criminals running around, but there's a perimeter keeping most of them corralled inside the prison grounds, and the most dangerous prisoner, Menton, isn't free yet--.
 * Late in Cave Story, you get trapped in prison cell. Getting out is as easy as talking to an NPC who also sits there.
 * In the Dragon Age expansion, Awakenings, there is the new party member Anders, an apostate mage who has escaped from the Templars seven times.
 * It's laughably easy to escape Fort Drakon in Origins too, There is only one easy to fool guard (and he has the cell key) in the same room as your cell, and all of your equipment is in one chest—that is also in the same room. The cell isn't even one of those special doors that can't be lockpicked. There are also spare guard uniforms a couple rooms over too.
 * In Dragon Quest III, you get locked in a prison cell... in a castle which requires that you have the jail-opening key to even get inside.
 * In Legend of Dragoon you're locked up for all of 5 seconds in Zenebatos before smashes through the wall and releases your party
 * Breath of Fire has a prison in Auria that the main characters may get locked in any number of times. There's a man inside the cell, asleep, who will simply let you out the front door if you talk to him.
 * The plot of Paper Mario requires you to break out of a cell several times using a secret passage. That leads right into  room.
 * Dark Souls starts out in one of these. There aren't any guards and only a few hollows, only some of which are hostile. The prison is also in complete disrepair. There is also the 20 foot tall Asylum Demon, who makes things somewhat challenging. It's pretty clear that undead are just dumped in there, starter equipment and all and left to rot.
 * When you first turn up to talk to the King in Shining the Holy Ark you're literally dropped into the dungeon. A good 2 minute conversation later and you're being let out by your ninja friend and then escaping via the secret underground passage...that is linked to the dungeons.

Web Comics

 * The Order of the Stick: In this strip, Roy justifies working with a Chaotic Evil halfling on the grounds that all prisons are cardboard to him, and this way he can be put to some good use. Considering that as of #745 they are both held in prison, but Roy won't let Belkar break them out....
 * To be fair, the other characters have proven time and time again that all prisons are cardboard to any high-level character.
 * Inverted when Roy suggests locking up the Linear Guild, on the grounds that in a world of Death Is Cheap, killing their prisoners would actually be less effective than locking them up. Once your allies can start casting Resurrection, the afterlife itself becomes a Cardboard Prison.
 * Freefall. All jails are made of cardboard if you're an alien squid.
 * It's not so much that the jails in Schlock Mercenary are made of cardboard as the characters are just brilliant at escaping, which isn't so hard when you wear low-profile power armour, which they generally get to keep since it looks like regular uniforms. In addition, the title character can basically become any shape he wants, and thus they have to use shields to contain him.
 * Bob and George. George can break the Author out with no trouble at all.
 * Everyday Heroes has a typical revolving-door prison.

Web Original

 * Star Harbor Nights pays tribute to Arkham with Dunwich Asylum. Mad scientist Rhyme cheerfully accepts the fact that she'll eventually be caught each time she escapes, as she knows she'll get out again.
 * Regularly breaking out of prison is considered a viable PR strategy for the villains of Super Stories.
 * Spoofed on Homestar Runner in the aptly-named "Strong Bad Is In Jail Cartoon". The "jail" Strong Bad is put in is literally a cardboard box with a hole cut into it, and Strong Mad frees him by lifting the box and throwing it away.
 * Strong Mad also baked a jackhammer into a "cake" for Strong Bad, but it turned out to be unnecessary.

Western Animation
""But you caught the bad guy. The Joker's back in Arkham for, like, the seventy-ninth time -- where maybe we can hold onto him for more than an hour and a half this time...""
 * In Challenge of the Superfriends Sinestro, Black Manta, and Cheetah escape from a cell by Sinestro just walking into the anti-matter Universe of Qward and the others following him.
 * An entire episode in Batman the Animated Series is dedicated to a former brutal Arkham security officer turned vigilante out of disgust with Arkham's poor track record. He actually said that as far as villains are concerned, Arkham has rotating doors.
 * In another, Robin wryly mentions that the recent breakout of Mr. Freeze was the "most elaborate escape from Arkham this year".
 * And yet again in "Jokers Wild", The Joker manages to escape from Arkham in all of about 45 seconds after seeing a news broadcast about the new Joker-themed casino opening in Gotham. However,.
 * In "Judgement Day", one of the city officials endorsing the Judge (who uses lethal force on criminals) says Arkham is like a revolving door.
 * This is lampshaded in "Hush" by Dick.

""They took Eddie Nash to the madhouse. The real one, not Arkham.""
 * Also lampshaded in "Whatever Happened to the Caped Crusader?" by Alfred:

"Wiggum: Cuff him, boys. We're putting this dirtbag away. Snake: Ha! I'll be back on the street in 24 hours. Wiggum: We'll try to make it twelve."
 * Lampshaded again in "The Joker's Favor" when Charlie Collins threatens to blow up the Joker to end the threat to his family, pointing out that if he goes to Arkham he'll just escape again.
 * WOOHP's so-called high-security prison is a continual source of escaped baddies on Totally Spies!
 * Kim Possible reuses some villains this way, the ones who don't conveniently get away. Partly played for laughs at the beginning of the fourth season, where two episodes feature another villain breaking Shego out of prison and leaving Drakken behind, including his own cousin. Drakken is eventually freed by an alien Amazon, which, to be fair, the prison can't really have been expected to foresee.
 * The Teen Titans series starts off with the gang going to control a prison break. (Oddly enough, it was a bad guy breaking in instead of the prisoners trying to break out.)
 * The trope isn't just limited to this galaxy, either. When questioned on her reappearance, as she was supposed to be locked up in some galactic prison, Blackfire nonchalantly commented, "I got bored, so I broke out."
 * Sideshow Bob on The Simpsons is constantly getting out of prison by one way or another. One episode revealed that the Springfield Minimum Security Prison has an unlocked gate, and the only thing keeping prisoners inside is the honor system. Fellow prisoners yell at Snake for "ruining it" for the rest of them when he escapes to take revenge on Homer for filling his car up with cheap gasoline.
 * Bob has only really escaped twice: once by sneaking away while working at the Air Force base and once by disguising himself as his cellmate. More often than not he was released legally, albeit for highly questionable reasons: "No one who speaks German could be an evil man! Parole granted!"
 * In an early episode, Chief Wiggum agrees to let out a bunch of prisoners so they can watch the little league hockey finals, but only if they promise to come back afterwards. When the prisoners refuses to even pretend that they'll agree to do this, Wiggum lets them out anyway.
 * "The Springfield Connection"

"XR: "Lasers"... "Acid"... "Escape From Prison"! So that's how he keeps coming back!"
 * Homer takes this literally when he goes to Japan. His jail cell is literally made out of paper. So he just walks through it.
 * On DuckTales, the ease with which the Beagle Boys get out of jail countless times (usually with the help of cakes with poorly disguised tools inside sent by Ma Beagle) became a running gag.
 * In one episode, the prison staff decide to X-ray one of Ma's cakes to put a stop to this. Though there's no tools baked inside, whatever recipe Ma used makes Burger Beagle (who devours it in quickly) jitter so much his brothers use him as a JACKHAMMER.
 * Lampshaded in Buzz Lightyear of Star Command: XR and XL switch heads, and XR (with XL's body) is thrown in Star Command prison. While looking at the different buttons on XL's arm, he makes a startling discovery:

"Duke, concerning Cobra Commander: "We flew in, beat 'em like mixed race step children and Cobra Commander went to prison... and he promptly escaped. Whoo boy the other countries of the world where pissed, they wanted him put to death immediately, but we kinda dragged our heels and by that time Zartan had busted him out with a wicker basket thing and a remote control sneaker or something... ahhhh good times.""
 * The ghost containment unit in The Real Ghostbusters is particularly unreliable. The marshmallow man might as well have been meeting with a parole officer.
 * To be fair, it's actually very secure from the inside. Most of the break outs are some idiot (Slimer) shutting it down.
 * One story featured a ghost who kept breaking out of the ghost traps no matter what the Ghostbusters tried. Ultimately he turned out to be the Ghost of Harry Houdini and fortunately was actually a good guy, negating the need to try putting him in the containment unit.
 * Pretty much every incarnation of Carmen Sandiego, ever. The game shows are especially guilty of this.
 * In Where on Earth Is Carmen Sandiego?, the fact that the local authorities let Carmen escape just hours after Acme detective prodigy Lee Jordan made history by actually capturing her was the beginning of his Face Heel Turn.
 * Professor Norton Nimnul from Chip 'n Dale Rescue Rangers has been arrested countless times, yet he doesn't ever seem to stay in jail and always returns with new schemes.
 * Parodied in the Christmas special for Invader Zim. After convincing the worlds that he is actually Santa Claus, Zim orders that Dib be thrown in one of his jingle jails. Minutes after being locked up, Dib realizes the candy cane colored bars are made out of REAL candy canes. After breaking free, Zim finds him and orders that he be thrown in the "Actually strong Jingle Jail". When Dib asked why he didn't just put him in the strong one the first time, Zim replied with something along the lines of "Your puny brain can't grasp the genius of my evil mind."
 * In one episode of The Powerpuff Girls, some crooks manage to be let out of jail because there were some Powerpuff Girl costumes conveniently located in their cell.
 * That's nothing. One got out by making supervillains in the toilet. No, not from. In. Less disgusting than it sounds.
 * House of Mouse ran a Mickey Mouse short in which Mortimer gets him falsely arrested for theft. He manages to escape because the policeman guarding his cell is dumb enough to demonstrate the easiest way for a prisoner to escape—knocking him out and taking the keys.
 * Made fun of in Robot Chicken in a G.I. Joe Parody.


 * In Transformers Animated, Starscream is captured and placed in a holding cell on the Elite Guard's ship. Unfortunately they forgot to properly restrain him or take away his weapons, so he was easily able to blow up part of the hull and escape. In later episodes, it seems they actually learned their lesson from this incident.
 * The tie-in comics reveal that Starscream got his chance to escape while they were studying his flight tech. This trope is also used inconsistently with the human supervillains: the police don't even seem aware of Meltdown's first escape, but after that they stick him in a special cell not even his acid can melt through (he escapes, but thanks to the Dinobots following Blackarachnia's orders). On the whole, the comic-relief villains seem to have an easier time breaking out than the actual threats.
 * The Fairly OddParents: Though not a villain, Cosmo leads to an example of this when Wanda tricks him into a dog carrier when he needs to go to the D-O-C-T-O-R. Multiple times, it shows him easily having the ability to escape the trap, but he's too clueless to take any of the opportunities.
 * In El Tigre, the Miracle City prison sees mass breakouts virtually every day; in one episode, El Oso is blase about being sent back to jail because he plans on breaking out before dinner anyway. In a later episode, he's taken away in a police van and is immediately seen walking free seconds after.
 * In Sushi Pack, though most villains are shown going to jail at the end of each episode, only one villain has been consistently shown in jail. Lampshaded in one episode, as Ikura comments, "They need to start building better jails in this town!"
 * In The Spectacular Spider Man, the Sinister Six are broken out of a prison by the Big Man, and another time are broken out of a mental institution. Another episode even has Spider-Man testing out the security of the Vault in a sealed cell. Guess the results.
 * Actually, pretty good—though manages to remotely take control of the prison, he manages to eventually take control again with some help from.
 * In the old Birdman cartoon, a Gadgeteer Genius once broke out of prison by constructing a suit of Powered Armor complete with a jetpack in the prison metalshop. After Birdman kicked his ass and sent him back to prison the episode ended with the warden deciding to assign the guy to prison laundry duty instead of the metalshop, thinking the guy wouldn't be able to turn this to his advantage. The villain proved him wrong in a later episode when he escaped again by converting a dryer into an escape rocket. After Birdman caught him again, the warden finally wised up and sent the villain to work in the prison library, far away from any machinery.
 * This happens in Avengers Earths Mightiest Heroes in the very "first" episode. There's a massive jail break at the four supervillain prisons (The Vault, The Cube, The Big House, and The Raft) which creates the need to form The Avengers. We don't know the history of the prisons beforehand aside from the fact that they were tailor made based on the type of supervillian they held. (The Vault had tech chriminals, the cube radiation criminals, the big house genetic villains, and The Raft had the most dangerous criminals) Seeing how someone broke into the Vault in one of the backstory micro episodes, and two inmates had apparently broken out of the Cube in the past (Hulk and absorbing man), they don't sound too great.
 * Regardless, all these prisons are presumably abandoned for prison 42, the above mentioned "fantasy island" of comic fame. Unlike comics, this prison has functioned just as designed, and despite the less than friendly environment, is generally considered a good idea in universe.
 * During an imagination episode of The New Adventures of Winnie the Pooh that portrayed a Wild West train robbery, Pooh and Tigger are put in a one of these. Not only were the bars wide enough for the characters to walk through (and they do), but also there was no back wall.
 * Family Guy parodies this with "Canadian Alcatraz", where the guards routinely let prisoners out, as long as they're back by sundown.
 * Subverted in the 1990s X-Men cartoon: Magneto breaks Beast out of jail in episode 3, but Beast just stays where he is.
 * In Adventure Time, Finn is imprisoned in a cage made out of sticks. After his captors decide he's no longer worth holding captive, Finn asks them to let him out of the cage, but they tell him to take it apart himself since it's so flimsy.
 * It's not technically a prison, but Tweety Bird at times could fly between the bars of his cage any time he liked (it was usually mentioned that he stayed in voluntarily because Sylvester couldn't get in.)
 * Gargoyles subverts this while playing it straight. While the Pack are in jail, a stranger in Powered Armor breaks in to help them escape. The Pack is more than happy to do so, but Fox refuses, stating he'll serve out his sentence. Of course, since this is Gargoyles we're talking about, it all turns out to have been a scheme by Xanatos Gambit. He sent the Powered Armored man, and Fox was told to stay behind so that she could get out of jail early (and legally) for good behavior.

Real Life

 * "Open prisons" do exist in real life, where "escaping" can often be a simple matter of walking off the premises. However, these are only intended to be used for extremely low-risk prisoners with crimes like avoiding fines and petty vandalism (and usually who have a life outside that it's not worth throwing away for the chance of escape); if someone actually does escape it's the fault of the prison service for assigning them to that facility, more than that of the guards.
 * In a similar trend, there are European countries where the only criminal charge associated with escaping from prison is the theft of one's prison uniform; mail it back, and an escaped prisoner won't have any time added to their sentence. That isn't to say they won't be made to resume their sentence if recaptured, however.
 * For the first 40 years of Folsom Prison's existence, the prison had no perimeter wall. Instead, the prison relied on the presence of six gatling guns to intimidate prisoners into staying put. Prisoners who made escape attempts were identified with a (hilariously appropriate) Red Shirt.
 * Pablo Escobar created the very prison he was sent to. He was still able to excute his enemies and commit drug trafficing deals. Many civilians claimed to have witnessed him in public while he was 'in prison'. Soon government troops raided the prison and faced a significant cartel force shooting back at them while Pablo escaped his 'prison'.
 * Joaquín "El Chapo" Guzmán Loera, a Mexican drug lord, managed to get out of a maximum security jail with little to no effort. Of course, he and his associates had to pull some mind-boggingly huge strings and had to spend shiploads of cash to do it, but his case caused such a massive outcry in the media, that the jail from where he escaped, called "Puente Grande" ("Great Bridge"), was nicknamed "Puerta Grande" ("Big Door").
 * Harry Houdini claimed (and was able to back up) the ability to escape from anywhere. He toured England, Scotland, the Netherlands, Germany, France, and Russia. In each city, Houdini would challenge local police to restrain him with shackles and lock him in their jails. In many of these challenge escapes, Houdini would first be stripped nude and searched. A police officer is reported to have said he was very glad Houdini was not actually a criminal.
 * Houdini once performed this trick in the Tower of London. No matter what he did, he could not unlock the door. Then, on a hunch, he tried the door handle and found the door opened. The jailer, in an attempt to fool the magician, had deliberately not locked the door.
 * Jack Sheppard escaped from a London jail four times in succession.
 * Once within a few hours, once within a week, and the last two times in under two months each. It's amazing London didn't stop letting prisoners have bed sheets by the time he was done.
 * Scott Adams, the creator of Dilbert, wrote about such an occurrence in two of his blog posts (later published in book form). In the first he tells the then-current news story of a man who escaped prison by making a fake ID and a set of civilian clothes, and simply walked out. In the second post he reveals that the man had been caught outside a bar, intoxicated and making no attempt to hide his identity. Adams theorizes that the prisoner had simply forgotten something like a pack of cigarettes or a pair of sunglasses in his cell and got caught on purpose so he could retrieve them, certain that he could escape again. And that this time he wanted to try it drunk.
 * Willie Sutton. Broke into banks, broke out of prisons.
 * John Dillinger escaped from the Crown Point Jail (at the time it probably was the highest-security prison in the country, certainly in the state of Indiana) by carving a fake gun out of wood (or soap) and bluffed the guard into giving him his (real) which he used to take two men hostage, lock the entire staff in his cell, stole the sheriff's car and drove away.
 * This is one version of the story, anyway. According to another he bribed a guard to give him a gun, and made up the story in order to cover for him. And in Illuminatus-trilogy he claims that he walked through the walls.
 * On the other hand, this is largely averted in real life much more than it's Truth in Television. There's a great number of people that based their assumptions that any "especially dangerous" criminal could easily get out of any prison, when it's really quite far from the truth.
 * All it takes is a few high profile escapes, and that security is based on the assumption that it can fail, and putting in as many safeguards in to prevent it. Guards must go through an exhaustive background check, and their training has a high attrition rate for a reason. Also, some, such as military corrections officers, have a way of minimizing the risk of an inside job through simply reassigning them to a different facility every few years.
 * Toño Bicicleta was a Puerto-Rican criminal that was able to escape prison several times (seven times to be exact). The Next time the cops caught him, they didn't even bother arresting him and they just shot him.
 * Two men escaped a maximum security prison in Greece by being picked up by a friend in a helicopter. Twice.
 * Actually it was a rental tour helicopter. Which they took from the ROOF... Needless to say, many jokes emerged. (What is [escapee] doing in the prison courtyard? Checking in.)
 * A prisoner once accidentally escaped Fremantle Prison in Australia by being assigned to do maintenance on the prison wall, and falling off. Not wanting to harm his chances of parole, he simply walked back around to the main gate and asked to be let back in.
 * Socrates was supposedly put in one of these. He was put on trial for what amounted to asking lawyers really hard questions in public and making them look dumb. He was sentenced to either pay a small fine or death. They only wanted to publicly best him and were surprised when he chose death and tried to make an escape easy, so people wouldn't see them as murderers. The cell was left unlocked, guards would take frequent breaks, and he could have almost definitely have had a student bribe his way out, but never did for two reasons. The first is his philosophy on the issue and inevitability of him avoiding the situation again, and the second is that he saw it as an argument; by being executed, he proved the lawyers unjust.
 * This was frequent on the roughest frontier edges of The Wild West. As the real setting wasn't nearly as lawless as it's portrayed in fiction, building jails was a low priority. The occasional prisoner would be locked in a storehouse, an animal pen, or, in at least one case, tent-pegged down under a buffalo skin while awaiting trial.
 * Steven Jay Russell, the inspiration for I Love You Phillip Morris, escaped from prison so many times that his release date is now 2140.