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Greetings, convicts. Welcome to The Alcatraz. Around here, we like to call this place "The Rock". I'm sure you've heard of this place. We're on an island surrounded by boiling acid that just happens to be infested with sharks. There are guard towers every twenty feet and there are more Mooks here than you've had warm meals. The only way on or off this miserable spit of land is a narrow bridge, with explosives wired to it so we can destroy it at a moment's notice. We've got a perfect record here, and we're not going to lose it. So don't think about trying to escape, you miserable swine, you're likely to end up a blackened skull. There's no hope for any of you.
Well, except for you, Mr. Protagonist and your Ragtag Bunch of Misfits. I'm sure a combination of blind luck, poorly guarded air vents, the stupidity of my own men, and Deus Ex Machinas will be enough to ensure that you escape and continue on your quest. It's almost inevitable, whether you're breaking a loved one out or just escaping yourself. No one's ever escaped from here before, so of course you'll be the ones to do it. So enjoy your time here, you scum. God knows you won't be here for long. Now, guards! Take them to their cells, and let them rot!
What? Who says we're Tempting Fate?
Oh, and just so you scum know — this ain't your daddy's Cardboard Prison. Folks have been breaking out of that one for years now. Sometimes we make special precautions for a particularly bad prisoner: a Tailor-Made Prison that takes advantage of an Achilles' Heel you super freaks have or a Room 101 whenever prisoners need Cold-Blooded Torture or a Fate Worse Than Death in order to behave. We can be really nasty if we want to be. Ain't no one gonna remember you now. Might as well go to a happy place now, scum.
Compare Penal Colony.
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There was once an inescapable prison planet with high gravity in Outlaw Star. Naturally, it was only inescapable until Gene got involved. The fact that nobody had ever escaped is helped by the fact that the gravity has disastrous effects on the prisoners' health; nobody's ever served out their sentence because they all get heart attacks eventually.
Impel Down in One Piece, seen above as the page picture. It probably takes the cake as the worst prison in fiction. The only exit is also the entrance, as it is surrounded entirely by water. Since most inmates have eaten Devil Fruits, which give people super powers but robs them of the ability to swim, this automatically places Super Drowning Skills onto them. If one escapes, unless they can navigate past the battleships and water infested with whirlpools and sea monsters, water currents lead directly to one of two highly-guarded government fortresses, and even then only if they permit entry. It has six levels, each progressively worse than the last to house progressively dangerous criminals, and is filled with things just waiting to kill the unlucky prisoners, including the staff.
Level 1 is mostly a normal floor, though the highlight of Level One is the "Crimson Hell," a forest within the prison made up entirely of bladed "saber trees" and "needle grass." Prisoners are forced into it, being cut up at every turn and every step, giving the forest it's trademark red color, all the while being chased by poisonous insects and Axe Crazy prison guards. To add to the sadism the only way out is a pit located within the Crimson Hell, which leads to Level Two.(This was where Buggy was kept until the mass-escape, and it wasn't so bad for him, because he simply couldn't be hurt by the hazards here due to his Devil's Fruit power; for some reason, the guards never noticed that.)
Level 2 is the "Wild Beast Hell", where the cells are kept unlocked but the halls patrolled by ravenous creatures that feed off the prisoners kept within if they don't stay in their cells. Such creatures include manticores, basilisks, and a sphinx as the boss. Dozens of them (prisoners) are packed in somewhat small cells, so their only choices are to be killed by disease or be hunted.
Level 3, features "Starvation Hell", a vast, dry, perpetually hot desert. The prisoners here are kept floating in-between life and death with barely any water or food. There are corpses lining some of the cells, left to turn into dust (which is probably where all the sand came from).
Level 4, the "Hell of Scorching Flames," is even hotter than Level Three (in fact, it's the heat from this level that keeps the above one hot), as a gigantic "Lake of Blood" is kept boiling hot at all times, which prisoners are dropped into regularly. Other prisoners are used to keep wood on the fire at all times, where they face the risk of getting into a fight and being thrown into the "Lake".
Level 5, the "Hell of Freezing Cold," is the polar opposite of previous level, with below freezing temperatures and wolves that are so vicious, they actually preyed upon Level Two's beasts when they were initially introduced there, forcing their relocation. The prisoners kept here have given up on escape and rebellion completely, as they all stay locked in their freezing cells waiting to die.
Level 5.5: DRAG REVUE!: Unknown to even the Warden and his staff, there is a hidden "Paradise" where select prisoners can find a relative freedom. Prior to Luffy's infiltration, it is ruled by Emporio Ivankov, who has the ability to, among other things, gender bend people. With this ability, he offers newcomers to his "New Kama land" the opportunity to be whichever gender they choose. As of the Time Skip, Ivankov and the bulk of the prisoners he had recruited have returned to his homeland, and Straw Hats ally Bentham, better known as former Baroque Works agent Mr. 2 Bon Kurei, has taken over.
The generally unknown Level 6, the "Eternal Hell." Every (non-political) prisoner within is either a Lifer or on Death Row who caused incidents so serious the World Government sought to erase them from history. Among its inmates are Shilew (mentioned below), a former arc Big BadCrocodile, and the target of Luffy's intrusion into the place: Portgas D. Ace. Aside from the perpetual abandonment from the world, nothing else actually goes on here, mainly because you can't do much to such badasses.
To make this even worse, criminals go through a ritual when they first arrive where they're bathed in boiling water, which disinfects them and renders them sterilenote completely free of germs and other microorganisms. (This is called "baptizing" by the guys who are in charge, likely a sick idea of a joke.) Luffy is the only inmate known to escape this, as he was an intruder who had been poisoned and was not expected to survive longer than twenty-four hours. (Note that while the ritual is known to be agonizing, there are stories of incredibly tough inmates like Portgas D. Ace, Jinbe and Crocodile, who were able to withstand it without even flinching.)
There's also the people running the place. There is Sadi-chan, a chick with a dominatrix feel who commands the Four Demon Guards (highly powered Zoans); Saldeath, who commands the Blugori (giant mooks who hunt sea kings); Hannyabal, The Determinator Vice-Warden strong enough to brave all of the above tortures in only a loincloth; and Magellan, the Chief Warden, and one of the most powerful people in the World Government's employ. He can cover himself in poison to block direct attacks, cover a prison level in poison strong enough to melt stone, and create poisonous gas and other attacks. There was once also the swordsman Shiliew, the former Head Jailer, Magellan's Ax-Crazy near-equal, before he himself was confined to Level 6.
To highlight just how bad this prison is, one need only look at the two successful attempts to escape it. The only self-escapee had to cut off his feet and use his rare power of flight to escape. Luffy's break-in and escape with 241 other prisoners was only possible because of the assistance and chaos of the entire populations of levels 5, 5.5 and 6, Buggy, Mr. 3, and the timely intervention of the Blackbeard Pirates, one of the strongest crews in the world.
The Baccano!!Light Novels go the extra mile and use the Alcatraz as the setting of the "Alice in Jails" arc.
The moon of planet Micro in Transformers Victory. Almost the entire surface is covered in lava. On one of the few landmasses is an energy production plant, crewed by Decepticons who are given just enough energy to function, and are in constant danger of falling into a lava flow and melting.
In Bobobo-bo Bo-bobo, there's Cyber City. Ruled by Giga and the 6 Cyber Knights who runs many tortures for prisoners who tried to rebel against the Bald Empire.
Mega Unit, from Rave Master is said to be one of these. Unfortunately, it's never mentioned until Big Bad Lucia makes his entrance by breaking through its several yard thick solid steel walls with his bare hands and slaughtering all the guards, which gives it more of a Cardboard Prison feel
The anime of Wild Arms opens in a prison that set on a piece of rock that floats around on its own gravity above a bottomless chasm. The only way to get in or out is to either have flight transportation or wait a year till the rock passes the only bridge off it.
Sky Prison, the Undersea Prison and, the biggest, Honey Prison. Only Honey Prison has been shown in detail. Do not let the name fool you, Honey Prison is a nightmare, very reminiscent of the aforementioned Impel Down. Among other things, the prison lies above a forest of vicious monsters that will destroy anything that moves, "Execution Beasts" guard the inside, all of whom are controlled by the warden, and prisoners are served food with their favorite parts of them removed (Tthis is FAR worse than it sounds - see below). That's the first level. The other levels get progressively worse, with the final few levels being execution zones.
The First Level is the Appetizer course. As described, the Appetizer course is all about having the parts of one's favorite foods taken from them. Not too bad, right? WRONG. The "punishment" isn't just limited to the way the food is prepared; the prisoners themselves may be physically altered so that they cannot enjoy their favorite parts. For example, a man with a sweet tooth may have his brain rewired so that he cannot taste "sweet" flavors, while a marijuana addict may have the pleasure center of his brain numbed so that, even if he ingests the drug, he cannot derive its traditional effects (in turn leading to his going through withdrawals). Even by real world standards, that's pretty hellish treatment; in fact, it would fall squarely in the area of Cruel and Unusualnote It doesn't help that surgical repression is considered a crime against humanity, and was infamously practiced in Nazi concentration camps and The Gulag. And that's just the Appetizer.
The rest of the prison's "Full Course Menu" follows: the Second Level aka Soup Course involves edible, yet disgustingly smelly and bad tasting food, after that comes physical harm. With Fish, comes actual starvation, with the Meat dish, dehydration. People hardy enough to stand all that are then kept in Solitary Confinement with the Main Course, but then comes the Salads, Desserts, and Drinks. Respectively, those lead to being sliced up by knives, boiled alive, then finally seared with flame, before they drop your carcass over into the Death Season Forest, home to razor sharp trees and grass where the Shrike would feel at home. None of this is without the regular executions like quartering.
The setting of Mazinkaiser SKL is an island prison where three armies (well, really only two—Aira's Octagon faction is a peaceful Crystal Spires and TogasAmazon Brigade land implied to be the leftovers of a third, more violent faction) are kept contained by a gravity field. The Octagon, the Mad Max-esque Kiba faction and the feudal Galan faction all have a component of the field's generator. Unfortunately, the field is about to break and destroy the world...
Katekyo Hitman Reborn! has the Vindicare Prison. A place where those who break The Mafia law, are kept in a comatose state in liquid People Jars for eternity. Only known people to escape are Mukuro and his group. However, it is shown that someone on the outside can negotiate someone out through a deal.
Although it hasn't been shown, Big Lock from Kenichi: The Mightiest Disciple certainly qualifies. The description itself is not all that intimidating; "A prison for Master-level martial artists." Except that in this universe, "Master-level martial artists" are people who can run across water, move faster than the eye can see, make fissures by punching the ground, knock out Muggles with only a Death Glare, destroy tanks bare handed and punch holes in the hull of a battleship. And Big Lock can hold these people reliably enough that the good guys feel perfectly safe sending them off to there. Yowza. Then we find out that Master-level martial artists can easily break out. The only reason they don't is because they are following their code of honor that dictates that the defeated must honor the victors' wishes. That is the real reason the good guys feel safe.
Seventh Heaven in King of Bandit Jing. Otherwise completely normal, if very heavily guarded, part of its impregnability is unintentional: One of its inmates is a Reality Warper who has turned a part of the prison into his private sphere of influence, where anyone who enters is at his mercy.
Hinohara and Kotoha from Arata Kangatari are sent to Gotoya for the crime that Arata was framed for.
The titular title-featured Deadman Wonderland is Japan's only privately-owned correctional facility. Setting aside for a moment how insane that premise is, the place is really damn hard to escape. First of all, anyone who's on death row isn't executed on a particular day. Rather, they're fitted with collars that slowly inject a poison that will kill them after 3 days if they don't get the antidote regularly. So, most convicts can't even think about escape so much as survival, and escape is still forced away by death-traps and extremely bloodthirsty guards. Things are even worse if you're found to be a Deadman. If that's the case, they lock you in a hidden cell block that most people don't know exists, and keep you under surveillance by robots and extremely bloodthirsty guards with weapons that cancel your powers. A massive escape attempt midway through the series doesn't really have any illusions about getting any more than one person out. The point is to get info about the place's insanity to be seen by the government.
Bleach has the Nest of Maggots, a prison where Shinigami who are deemed too dangerous to be free are imprisoned. No zanpakutos are allowed, so all personnel are required to have sufficient hand-to-hand abilities to suppress any prisoner. Most prisoners are allowed to walk freely through the main chamber, while a rare few like Kurotsuchi Mayuri can also be chained in locked cells.
The research facility in Elfen Lied is a maximum security prison with extreme lockdown measures to ensure that the Diclonius kept there are not able to escape. Of course, the opening scene in the anime's very first episode immediately deals with one.
A second superprison was created in the Negative Zone dimension by Mr. Fantastic of the Fantastic Four, though it turned out that he was tricked into doing so as part of a plan by the Mad Thinker. Later, another prison was again built in the Zone, this time to hold the arrested superheroes during the Civil War series; no reference is made to the previous one there (or the problems it faced.)
There was also the Big House, where villains were shrunk down to action figure size so that even if they did escape, what harm could they do? Diabolical Mastermind the Mad Thinker organized a mass breakout, but the indication is given that nobody below his nearly superhuman level of intelligence could've done the same.
Marvel also has the Raft, which was introduced way back in New Avengers #1... where it was the site of a mass breakout. That's got to be some kind of record.
The Slab in The DCU. How secure was it? It was designed by Shiloh Norman, the greatest escape artist in history, to be escape proof. This man escaped from a black hole, but specifically designed the Slab to be too much even for him. The Joker organized a mass breakout in the Joker's Last Laugh event.
How long did it take him to think up the plan? Well, he was sort of thrown by being told he had terminal cancer, so it might have been closer to 10 minutes than his usual five.
Admittedly it is now much harder to escape from now that it has been relocated to Antarctica.
In The Dark Knight Strikes Again, The Atom is forcibly shrunken and kept in one of his own petri dishes, where he must constantly fight for survival against bacteria that are the relative size of dinosaurs.
Meanwhile in Teen Titans, they have re-opened the original Alcatraz, which is right next door to the Titans, so they can keep an eye on it. Unlike its namesake and like every other prison in The DCU, it is a Cardboard Prison.
The "High Rock" from the 2000 AD serial Harry 20 on the High Rock, which added to its inescapability by being in orbit.
The Phantom Zone from the Superman comics keeps prisoners in a ghost-like state in another dimension. It is so secure it survived the destruction of Krypton.
Belle Reve Prison is a special max security prison, with a secret purpose of being the secret headquarters for the Suicide Squad.
Devil's Due Publishing's G.I. Joe: America's Elite series had 'the Coffin'; a top-secret G.I. Joe-run prison facility in Greenland used to hold to captured Cobra operatives. It was extremely efficent until a mass breakout was orchestrated at the start of the "World War III" story arc.
X-Men Noir: Mark of Cain has Genosha Bay. It's on an island, next to a military base. Prisoners aren't allowed contact with one another or the outside world, and only get out of their cells for one hour of daily exercise, weather permitting. When Thomas Halloway, the Angel, gets out of his cell and spooks the warden, Professor Xavier catches him. Thomas manages to escape after about a week of sleep deprivation torture, and at the end of the series he's about to spring his buddies Captain Logan and Eugene.
Idées Noires: Three gags feature a man trying to escape from an impossibly-to-escape prison.
Diabolik has Asen, a supposedly unescapable prison mentioned in the first story as part of Diabolik's records: he was the first and only person who had ever broke out from there. A later story shows how Diabolik did it: he had been arrested while wearing one of his perfect masks before people knew of them, so when two guards arrived to 'soften' him up a little Diabolik beated up and killed the guards, disfigured the one looking vaguely alike his mask, stole his uniform and walked out maskless.
After his second arrest and the consequent trial with him swapping place with a drugged Jerkass Victim guy masked as him one hour before being executed, every time Diabolik is arrested he's kept in cells made only to prevent him from breaking out or Eva from breaking him out. He still breaks out every time, to the point that in one occasion two guards shot him as soon as they found out their prisoner was a masked Diabolik (he had broken out five minutes earlier).
The series also has a women's prison that actually is unescapable: the Swamp Prison, an extremely well-staffed jail surrounded by a swamp with a railway as the only way in or out. When Eva was imprisoned there, Diabolik had to resort to cause a cholera outbreak (Eva was inoculated against it) in it to get it evacuated and take her from the train, as he couldn't find a way to break in and take her out.
The Evronians from Paperinik New Adventures have the so-called Well, a planetoid where you can't escape but could be pulled out if the Evronians have a particularly dangerous job for a prisoner (hence the name). Keeping it unescapable is the simple fact that the only two Evronian presences there are the heavily fortified and garrisoned spaceport and a facility where the most dangerous prisoner of all, Trauma, is kept under constant surveillance from thousands of elite troops ready to disintegrate him from safe distance as soon as he tries and do anything strange. The only one who has ever broke out from the Well is Xadhoom, who had broken in to kill the second most dangerous prisoner (a cyborg that the guards kept there using his remote), killed him and then flew away, as she could survive and fly in space and the guards weren't stupid enough to even try and stop her.
Marvel/Star Comics' Planet Terry has the prison planet named Alphatraz, which Terry and his companions are sent to so they could find Terry's parents. However, the reason that nobody escapes Alphatraz is that the convicts have taken over the prison and have forced the guards to serve them.
There's Styx, an impregnable Decepticon prisoner, where the life-expectancy of its prisoners is very short, and only two known break-ins have worked.
Meanwhile, the Autobots have Garrus-9, a truly massive prisoner complex that takes a small army to break in to (Or a One-Man Army), mainly because they have weapon emplacements that take up whole buildings. It houses Autobots and Decepticons alike, the absolute worst of whom have their sparks extracted and placed in little boxes, just to make sure no-one breaks out. It also houses a lot of the Autobot's dirty secrets, which certain members of Autobot High Command place a higher priority on that, say, the staff or the prisoners.
In a flashback in The Transformers IDW, mention is made of Garrus-1, which is used to hold political prisoners, and anyone too visible to be sent to the Institute. Since it's on one of Cybertron's moons, it's probably a bit difficult to escape from than normal.
The Tower of Mists, Kandrakar's prison. Its inmates, some of the worst criminals in the universe, are kept inside individualized inescapable cells that are set up to invoke their prisoner's crime while punishing them (the two known cells are those created for Phobos and Cedric: Phobos, having done innumerable crimes in the pursuit of power, was tied up and drained of his magic, and Cedric, a shape shifter also known as the Prince of Lies, was locked in a cell showing a fake environment and filled with books containing nothing but lies (Cedric could appreciate the humour, and took to blatantly lying to any visitor to stay in the spirit of it).
All known inmates, that is Phobos, Cedric, Elyon (imprisoned there and shoved in Phobos' cell with a false accusation when Phobos managed to take over Kandrakar) and the warden himself, Endarno, managed to break out, but it took them something that should have been impossible: getting their hands on the key (the warden was neither corruptible nor a criminal). Every one of them had their method: Phobos used his last ounce of magic to switch bodies with Endarno, thus automatically getting the key; Cedric was broken out by Phobos after the above; and Elyon and Endarno were given the key from the new warden and helped by the Guardians of Kandrakar. Elyon, on the other hand, was so powerful that she could have broken out on her own, except she had expected some betrayal when she was arrested and placed all her power in the Crown of Light (and, in fact, later Cedric, after being recaptured, manages to evade imprisonment again by escaping the guards, entering in Elyon's cell and waiting for the Guardians to show up with the Crown while wearing Elyon's looks, after which he simply teleports out).
In the Sonic the Hedgehog fanfic Prison Island Break Shadow has apparently tried to escape Prison Island and failed - and apparently he's actually gotten the furthest of any convict. He's pretty angry at Sonic for insisting that he can.
Shadow: First the ankle cuff. Then the cell. Then the locked doors. Then the fences, the jungle, the MILES AND MILES OF FUCKING OCEAN! And all the fucking way, there's the Guard Robos, the cameras, the grasses, and that mother-fucking bastardated sonuvabitch Mephiles. You think you're the first to try?
In fact, Sonic talks so much about escaping this inescapable prison, that the other cons and guards think he's kidding. The "cuff" is an anklet permanently attached to both Sonic and Shadow. If either of them attempts to move beyond 30 mph, they get a debilitating shock. This is their paticular anti-escape measure; each prisoner has some kind of clothing or procedure that negates their talents/powers. Cells are self-explanatory, fences are the electric variety, and the jungle presents its own problems. Guard Robos are expendable Mecha-Mooks that can restrain and electrocute prisoners. Mephiles is the utter bastard of a Head Warden who keeps the prisoners distracted with fear of each other. He is fond of severely punishing anyone who attempts to escape, which serves as a deterrent for the rest. The ocean is the final obstacle of Prison Island. There are no convenient boats to steal and it's too far to swim or fly over. Shadow's attempt was stopped by the ocean, and he survived in the jungle for three weeks afterwards.
The relative merits of Facility 4028 (see Star Trek Online under Video Games, below) in this regard are discussed briefly in The Headhunt. Dul'krah remarks that "for a supposedly utterly secure prison, 4028 has had remarkable difficulties of late."
In Origin Story, the Gulag, Reed Richards prison, is specifically mentioned. One SHIELD agent hopes that they don't have to send Alex there for the rest of her life.
Films — Animated
Area 52 in Monsters vs. Aliens, an ultra-secret facility where monsters are locked away for... well, being monsters. No one escapes, however; they're released to fight the Alien Invasion.
From Toy Story 3, Sunnyside Daycare takes an unusually dark turn when Lots-O-Huggin Bear refuses to let the toys escape back to Andy, and has them jailed in the daycare's storage crates.
Chorh-Gom Prison, Tai Lung's mountain prison in Kung Fu Panda. He's the only prisoner, chained to the floor in a deep pit, wearing a tortoise shell-shaped suit with acupuncture needles that keep him paralyzed, and covered from above by massive crossbows at all times. There are one thousand guards responsible for containing him alone. He obtains one solitary feather, picks the lock and defeats the defenses in a few minutes.
The dungeons of Aquila from Ladyhawke: "Nobody ever escapes from the dungeons of Aquila. The people accept that as a historical fact." But Phillipe 'The Mouse' Gaston escapes anyway, during the movie's opening moments...
For bonus irony, that line is actually spoken after the discovery of Mouse's escape, to impress upon the captain of the guard the importance of recapturing him to maintaining the Bishop's power/reputation.
Or, perhaps, the importance of not telling anyone that Mouse had escaped, in hope that the incident can be covered up.
At least three of these are seen in The Chronicles of Riddick series. The second movie, simply called The Chronicles of Riddick, has Crematoria, where the prisoners stay in their underground prison because the sunrise sets the atmosphere on fire. Riddick outruns it. Escape from Butcher Bay is set in the virtually inescapable Butcher Bay prison (see the videogame section below for more details). A flash animation on one of the official websites featured Ursa Luna Slam City, which Riddick also escaped from.
Escape from L.A., where L.A. has broken away from the mainland and is now a prison island.
Fortress is a feature-length escape from a futuristic Alcatraz, the titular "Fortress" (located on a bunker deep underground, run by a sadistic warden and an equally nasty Master Computer, with intestinal Explosive Leashes, nightly Mind Rapes, automated Sentry Guns and heavily-armed cyborg Mecha-Mooks). Fortress 2 is a feature-length escape, by the same character, from a different futuristic Alcatraz. In space.
This is the premise of the film No Escape: the protagonist has broken out of five Alcatraz-type prisons which are really nothing more than tombs for the living, so the Warden dumps him in his private project — a Deserted Island surrounded by automated gunboats programmed to kill anyone who tries to leave.
Face/Off has the secret Erehwon Prison, located on an offshore oil rig, where every prisoner wears magnetic boots that can lock them in place on command.
You are now the property of Erewhon Prison. A citizen of nowhere. The Geneva Convention is void here; Amnesty International doesn't know we exist. When I say your ass belongs to me, I mean exactly that.
Outland. Marshall O'Neil keeps a prisoner in an airless zero-gravity cell, suspended in a spacesuit. Unfortunately the prisoner's helplessness makes it all too easy for someone to kill him by cutting his air hose.
Most of the film The Rock takes place on Alcatraz island. Inverted since the bad guys capture it and turn it into a fortress, so the Navy Seals get help breaking in from the one person who successfully escaped.
The prison camp in The Bridge on the River Kwai was allegedly inescapable due to its remote location deep in the Burmese jungle. Naturally, this was proved incorrect.
Colonel Saito: "A word to you about escape. There is no barbed wire. No stockade. No watchtower. They are not necessary. We are an island in the jungle. Escape is impossible. You would die."
The prison camp in The Great Escape was specifically designed to be escape-proof and housed the most frequent troublemakers/escape-attempters among the POW populace.
The Pit in The Dark Knight Rises. Like the name implies, it is a giant pit deep into the ground. There are no guards or booby traps or locked doors, just a tough climb and a jump that is just too far for 99% of people to jump.
Einsargen Prison, built at the bottom of the deepest mine ever sunk in East Germany and made specifically to hold Cobra Commander and Destro, in G.I. Joe: Retaliation.
Escape Plan: The Tomb is designed to be completely escape proof — the prisoners are drugged before being brought in, blindfolded when moved about, and are allowed no contact with or even visual access to the outside world; the cells are elevated and transparent, and surrounded almost completely by surveillance; the guards are masked and work in scrambled shifts so that the prisoners can't plan around their shifts; all the doors have magnetic locks in case of emergency; and to top it all off, the Tomb itself is built inside an oil tanker anchored in the middle of the ocean.
In X-Men: Days of Future Past, Magneto is kept at a high-security, all-concrete prison right in the center of the Pentagon. Considering he was arrested shortly after the JFK assassination (1963), this jail has successfully restrained one of the most powerful mutants in the world for ten whole years.
Holes has Camp Green Lake. See the Literature section below.
Guardians of the Galaxy has the Kyln, which is difficult to escape from by virtue of the fact that it's a space station, requiring a carefully laid plan to get a ship in order to escape. Of course Rocket, being something of an escape artist, comes up with a plan to bust out pretty quickly.
It's even worse when you learn that the abducted prisoners taken are brainwashed and mutated into new Blacksuits.
Gouffre Martel in Alfred Bester's The Stars My Destination isn't a rock in the middle of the ocean but instead an underground labyrinth in the Pyrenees always in darkness. Still, Gully Foyle and Jisbella McQueen manage to escape.
Azkaban from J. K. Rowling's Harry Potter combines the "rock in the middle of the sea" with guardian creatures called Dementors who suck all happy feelings out of you, ensuring that prisoners go depressed or insane long before they can escape. It's stated that Azkaban has high iron walls but doesn't need them, since the Dementors make the inmates imprisoned in their own minds. The following people escaped from it.
Sirius Black broke out, because he could transform himself into a dog which has less complicated emotions than a human (and thus couldn't be sensed by the Dementors). He kept himself (more or less) sane by reflecting on the fact that he had been betrayed, which was not a happy thought, and therefore could not feed the Dementors.
Bartemius "Barty" Crouch, Junior also broke out of Azkaban. In this case, his dying mother switched places with him, and the blind Dementors only sensed one person coming in, one going out.
The mass breakout in Harry Potter and the Order of the Phoenix, happened with the cooperation of the aforementioned guards. It's also implied that there are later breakouts, but that the government tries to cover them up.
The Warden Diamond from the Jack Chalker series The Four Lords of the Diamond is a solar system with four habitable planets infested by a microrganism that kills anyone who tries to leave, making for one huge, seemingly inescapable prison colony.
The titular prison in ''The Omega Cage by Steve Perry and Michael Reaves. It's on a deathworld, and many hundreds of kilometers from any way to get off the planet.
The narrator in Adam Roberts' novel Stone must escape from a prison (which, judging by its description, bears a disturbing resemblance to Teletubby Land) in the core of a star, and can only do so with the aid of a conspiracy of the Nanomachines that keep the society's technology running.
The Lusankya facility in the Star Wars Expanded Universe is supposedly inescapable until a member of Rogue Squadron shows up. It's actually unknown whether or not anyone else escaped- the guards returned those who apparently tried to escape as blackened corpses, making it impossible to tell if they were really the ones who tried to escape. They tried this same trick for the one who did escape. (Given that the Super Star Destroyer in question only launched once a successful escape had been confirmed—though Isard was initially wrong about who escaped—it's probable that the only successful escape was that Rogue Squadron member.) It helps that the prison had a clever way to lower the chances of a successful escape: the prisoners were kept in an area of reversed gravity, so any attempt to escape up and out of the facility would instead go deeper into the facility—a fact discovered by the lone successful escapee.
Lusankya is known to be where the Big Bad turns Rebels into Manchurian Agents; apparently there had been several times when a Rebel who had been captured came back into service after escaping a lesser prison, and had no memory of Lusankya until Isard started telling them what to do. Tycho Celchu escaped a lesser prison but actually remembered Lusankya, which put him under suspicion.
The prison planet Hades in the Honor Harrington series. She escapes. With 500,000 other prisoners. Although to be fair, the guards thought she was dead, and she "smuggled in" two spaceships plus enough weaponry for a small army.
In The Book of D'ni, Veovis escapes not once, but TWICE from the inescapable Prison Ages, the second of which was written explicitly for him, by four different writers, checked and altered by the highest of the high council, and the book burned after he was linked through.
The Stars' End interstellar prison in the Star Wars novel Han Solo At Stars' End. Han Solo blasts it into a high-arc trajectory. Does it even count as a prison escape when you take the whole prison with you?
From the same galaxy far, far away is Oovo IV, a supermax-style prison built into a barren, airless asteroid that's constantly pelted by meteor showers; if you somehow get out, chances are you'll want back in.
Camp Green Lake in Holes. Mr. Sir even points out that there are no towers, fences, or barbed wire. The kids are free to run off anytime they want, but there's no way they'd last more than three days. They would die either from thirst or the hostile fauna. Even the guns most of the staff carry on them aren't for keeping the kids in line. They're for killing any stray scorpions or yellow-spotted lizards that enter the camp.
In the book I Want To Go Home! by Gordon Korman, Camp Algonkian Island is nicknamed Alcatraz, and the two protagonists spend the entire summer trying to get off the island.
Subverted in the Forgotten Realms novel, The City of Ravens, where the protagonist, despite what powerful magic and magical artifacts he possessed, really couldn't get out of the prison. It took the hiding warlord who got him imprisoned in the first place to get him out and she was able to do so because she was hiding as the city's mayor.
In the Vorkosigan Saga story "Borders of Infinity" Miles has to organize an escape from the "escape proof" Dagoola IV Top Security Prison Camp #3. The "camp" is a masterpiece of psychological warfare, quite possibly the most terrifying prison in existence while still meeting the future equivalent of the Geneva Conventions. It's just a giant dome over an open space on a remote planet, with no resources, no buildings and no guards, just ten thousand prisoners. The captors drop the legally required amount of food in a huge pile out in the open, ensuring that prisoners riot and fight to get it. Pretty soon, most of the prisoners are all in armed tribes too busy fighting each other over supplies to organize an escape, and the rest are too starved or demoralized to do anything. Miles is sent to enact a two-prisoner rescue thus proving that it was escape-proof... just not rescue-proof. Miles plans ahead. For Miles, Plan B is alwaysRefuge in Audacity, so instead of rescuing two prisoners, he rescues all of them.
The Chateau d'If from The Count of Monte Cristo where Edmond Dantes was sent after being betrayed by Fernand Mondego. Prisons such as these back in medieval and renaissance times were for people who were too politically important to simply execute or have murdered, as maintaining the prison and feeding the prisoners cost serious money.
Xintan Prison from The Six Sacred Stones is situated atop twin mountain peaks, where the only way out is a single train line. The main prison is on one peak, with a torture wing on the other peak, and the only way out is a train line into the main prison. Naturally, the mountains are too steep to ski down and they have helicopters ready to chase down anyone stupid enough to parachute. Naturally, it's inescapable until the heroes try it.
In Seven Ancient Wonders, the heroes break a guy out of Guantanamo Bay in a surprisingly straightforward plan. Notably, it involves landing a 747 on the facility's golf course as a diversion.
Codex Alera has the Grey Tower, a prison structure built to be able to hold the most powerful Furycrafters around, up to and including the First Lord if need be. Along with the many powerful Furies guarding the building, the prison's guards, the Grey Guard, are hand picked for loyalty to the Realm and have never taken a bring in over 500 years. due either to honesty or the fact that they can receive twice the amount of the bribe by turning in the person who tried it. Only two breakouts have ever been successful, both perpetrated by the main character Tavi. The first was fairly straightforward, but the second ran into trouble thanks to security upgrades Tavi himself introduced following his first attempt. Notably, however, these breakouts happened because the Grey Tower was initially designed to specifically contain and neutralize furycrafting. As was the case with a lot of Aleran engineering, no one ever even considered the possibility that someone would be insane enough to attempt a breakout without using furies, which is exactly how Tavi managed it the first time. The second time, Tavi exploited his own designs to get in and out of the prison.
Barad-dûr in The Lord of the Rings. Tolkien states that those who enter as prisoners do not leave. Ever. Gollum claimed to have escaped, but Gandalf implies it was part of Sauron's plan to get the Ring and therefore he was released.
Cirith-Ungol. It's at the top of a virtually impassable mountain pass, one direction leads to Mordor, the other leads through a labyrinth guarded by a giant spider. When Frodo is imprisoned there, he only gets out because Sam takes up Sting and the Ring in order to rescue him.
The prison cells in the Eyrie in A Song of Ice and Fire are actually ridiculously easy to leave: this is because they are lacking an outside wall, meaning that prisoners can just step outside. Since the Eyrie is several miles up, however, doing this would result in a gruesome death.
To make matters worse, the wind howls day and night and the floor is in a slight downwards incline, meaning that prisoners often can't sleep due to the noise and the fear that they will roll off the edge. Unsurprisingly, most of them go mad and end up jumping off.
The remote Swedish asylum in The Stars' Tennis Balls by Stephen Fry which, in keeping with the book's nature, is a modernised Chateau d'If.
Alien3 - it's inescapable because the entire planet is the prison - basically a place where everybody ships off their bad people to fend for themselves.
In Cold Days, the fourteenth book of The Dresden Files, it is revealed that Demonreach is a prison designed to hold extremely dangerous magical beings and Eldritch Abominations. How dangerous are these beings? Well, remember the Skinwalker from Turn Coat? the thing that almost drove Harry insane just from Seeing it? Demonreach has six of them... in the minimum security wing.
In Adventure Hunters there is an infamous prison reserved for the worst of criminals that is located at the bottom of an ocean. The only way in or out is a ship that leaves once it delivers the newest inmate. This is the ultmate fate of Ryvas; life imprisonment for breaking the Nuclear Weapons Taboo.
Ananke Alpha in the Star Trek: Deep Space Nine Relaunch is a spherical prison built in a remote star system with no planets. It was originally designed to hold the most dangerous criminals in The Federation. By 2381 it has just one prisoner - the Female Changeling that led the Dominion.
Stoneveldt in the Parker novel Breakout has this reputation. Parker is told multiple times that no one has ever escaped from there. The title of the novel may tell you what Parker proceeds to start planning.
Woken Furies has Rila Crags, an infamous prison used by the Harlan family to inter political enemies. According to legend, only one person ever succeeded in breaking in and getting out again. The protagonists end up having to plan their own break-in in order to rescue a prisoner.
Live Action TV
The Alcatraz featured in MythBusters. In a first season episode Adam and Jamie tested whether or not the prisoners who executed the famous 1962 Escape from Alcatraz might have reached land. They built the same kind of rubber boat the prisoners did, using authentic materials, and launching from the same place the prisoners did at the same time of night. They did not bother attempting the escape plan, paddling north to Angel Island—apparently nobody thinks the convicts had a chance of getting there—but they did successfully reach the shore of the Marin Headlands, at the north end of the Golden Gate Bridge.
The Prison Luff in Space Cases, where troublesome prisoners are punished by a Mind Wipe, erasing their memory.
For season 3 of Prison Break, hero Scofield is manipulated by the recurring shadowy conspiracy to break a man out of Sona, a fictional Panamanian prison with a perfect record, surrounded by brutal military forces, and that's run by the convicts. Fox River in season 1 is not this trope, since it is more of a standard maximum security prison, even though it took the protagonists the entire season to break out.
Supposedly, in Andromeda, "no one escapes from a High Guard prison". It's shown to be a small cell with a bench, with sophisticated technology like 24/7 monitoring, pressure sensitive walls, isolation, and walls, floors, and ceilings that can't even be scratched without expensive tools. However, in that same episode, Dylan and Harper escape because someone paid off the jailer, and an assassin escapes with the help of her brother. So, it would be more accurate to say "no one escapes a High Guard prison without help".
SG-1 had to break into and then break out of Sokar's prison moon that was designed to be a literal hell on earth <insert random planet>.
Another episode featured a Race-Of-The-Week whose Hat was a ridiculously harsh justice system, and who created their prison by removing the DHD on a planet and sending prisoners on a one-way trip through the gate. It goes without saying that SG-1 annoy the locals and are sentenced to go there. Aiding the release of a fellow prisoner was shown to be a very bad thing when she turned out to be insane and evil, making it a prime example of why you should be careful when freeing people from a super prison.
Inverted with Stalag 13 from Hogan's Heroes. It's the only German POW camp with a perfect record, but specifically because the prisoners keep it that way. If anyone escaped their kommandant would be replaced with someone who was actually competent and they wouldn't be able to run their underground organization from inside it.
The Pandorica in Doctor Who. A cube a few metres across, stated by the Doctor to contain the most dangerous being in the Universe and to have multiple locks. When the Doctor comes across it it is being unlocked apparently from within, while many powerful species are gathered around it. When it finally opens, the Pandorica is empty, as it is revealed that the most dangerous being in the Universe is the Doctor himself, who is then imprisoned in it. Rory breaks him out with help from the Doctor's future self. Interestingly, despite the claimed security of its locks, they are easily opened by a sonic screwdriver. It's actually a set up by all of the Doctor's greatest enemies, working together to trap him forever.
It's so impenetrable that it can survive the very end of the universe.
Obviously, the only safety measure they forgot was a deadlock seal.
Another supposedly "perfect prison" is brought in later by Canton Delaware III to trap the Doctor. It is made of over a hundred bricks of the densest material in the universe, while it's prisoners are left inside with no food or water. It would've been perfect, had Delaware not been merely pretending to work for the Silence.
The prison in the episode "Angels in Chains" of the 2011 series of Charlie's Angels. Oddly for this trope, the Angels don't actually manage to escape and are instead caught during their escape attempt.
One Job of the Week for the crew of the Tulip in Starhunter involves transporting the first two lifers to a newly built jail-on-wheels that stays on the sunny side of Mercury at all times. The prison is tended entirely by robots, and getting there involves landing at prearranged coordinates on the dark side and taking a robot-driven car the rest of the way.
In the Star Trek: Deep Space Nine episode In Purgatory's Shadow showed us a Jem'Hadar interment camp. It's a hollowed out asteroid. Break out, and only the cold vacuum of space is there to greet you.
Similarly the Star Trek: Voyager episode "The Chute" has a prison in a hollowed out asteroid. The prisoners think they're underground.
In Arrow, Purgatory — the island Oliver was stranded on — used to be a secret prison where the Chinese military kept its most dangerous prisoners. There were no cells or guards, the prisoners were just abandoned on this island in the middle of nowhere and left to fend for themselves. The Season 2 finale reveals that A.R.G.U.S. has at some point taken control of the island and built actual underground cells.
Agents of S.H.I.E.L.D.: There are repeated mentions of the Fridge, SHIELD's maximum security prison/storage facility, which is implied to be one of these. Eventually, it's revealed that it's a massive tower with no ground-level exits, only one entrance/exit on the roof accessible by helipad, and the door is reinforced to such an extent that the machinegun on a gunship fails to penetrate.
BIONICLE had the Pit, where those who had broken the law of Mata Nui were sent by a being named Botar (and following his death, a Suspiciously Similar Substitute) after being defeated in battle. Hundreds of years ago, it filled up with mutagenic water and the interns escaped, and more recently, the entire establishment was destroyed, however by that time, most of the escapees had been recaptured.
Older Than Feudalism: Greek myth has Tartarus, where titans, demons and a few choice humans are kept.
Eberron has Dreadhold, a politically-independent island prison run by the dwarves of House Kundarak. The island has a connection to Lamannia, the plane of primal nature, which massively increases the durability of wood and stone while also negating most magic used against it (including magic used to teleport or phase through it). The same effect also keeps food and drink eternally fresh and destroys all poisons. A small village exists on the island to reduce dependence on imports, and most communication with the outside world is conducted through magic. Before a person can even visit the island they must consent to having their mind read and being placed under curses which limit their combat ability; shapeshifters must also wear distinctive clothing at all times to prevent impersonation. The prison itself is surrounded by a pitch-black cloud which prevents anyone from seeing inside by physical or magical means, and is patrolled from the air by manticores. The only way in or out is through an Anti-Magic corridor filled with heavy gates and armed guards. The hallways are filled with boobytraps which variously attack, cage, knock out or mind control anyone who passes through without authorisation, and are constantly moved around to prevent prisoners from mapping them. The guards are all members of House Kundarak, meaning they have the power to create magical wards and locks, and many have been given the ability to communicate telepathically (both with each other and with their associates on the mainland). The equipment at the guard stations includes a modified scrying device that can see invisible creatures and analyse magic, as well as alarms that sound if any of the wards on the island have been activated, and controls for a set of invisible forcefields that run throughout the prison; all of these function only for members of the Kundarak bloodline. Due to the prison incorporating a Kundarak research facility, a number of powerful wizards are usually nearby and can be called on for backup. Finally, in addition to the living guards the prison is also patrolled by a number of constructs known as Slaughterstone Eviscerators. Extra-dangerous prisoners are sent to the Stone Ward, where they are petrified for the duration of their stay. Incredibly dangerous prisoners get sent to the Deep Ward, which lies at the bottom of a frictionless pit accessed through a single cableless elevator, and is kept in complete darkness at all times (relying on the dwarf guards' ability to see in the dark). Each cell in the Deep Ward is a Tailor-Made Prison with features such as magic negation, sound negation or indestructible walls... and some of the inhabitants are petrified too, just for good measure.
Sigil's prison is simply called The Prison, and it's very secure. (It was also where the Mercykillers, the group in charge of corrections, made their headquarters in the city.) The Mercykillers have an even more secure prison for the worst criminals called The Vault in Carceri. (How secure is it? Let me put it this way, Carceri is what planar beings call the place that mortals from the Prime Material Plane call Tartarus. Yep, the very same place where the Titans are locked up). And if a criminal does something where the Lady of Pain herself has to intervene (which is rare; she only does so if someone tries to let the gods into Sigil, tries to worship her, or causes so much unrest and chaos that people no longer feel safe) there are the Mazes, dimensional labyrinths that she imprisons transgressors in. Essentially, this is a life sentence of solitary confinement, but there is a way out; it's just very difficult to fine. (Note that this is considered the lenient sentence. Offenders who catch her in a bad mood are flayed alive by her gaze.)
The Splat book Fiendish Codex II: Hordes of the Abyss mentions the 73rd layer of the Abyss, the Wells of Darkness. This place contains many inky, black pools of thick liquid, each one a Tailor-Made Prison for a very powerful and destructive demon or Eldritch Abomination that was sealed here by a Demon Lord, god, or group of gods. The most dangerous prisoner here is Apep, the King of Serpents who once daily challenged the Egyptian god Ra on his journey through the Twelve Hours of Night. Security is maintained by demonic zombies called bodaks, and some of the wells have additional guards. (In Apep's case, it's a bigger than average blackstone gigant, one of the most powerful golems known.) Escape is possible from this place, either through intervention from the gods or the Lords of Woe, but it's only happened four times in the eons-long history of the place. Surprisingly, the bodaks do not bother mortals or normal residents of the Abyss who only make brief visits (after one to four hours, you've overstayed your welcome, and they try to kill you) and some people do come here. Either they're servants of a prisoner who are foolish enough to think escape is possible or who try to ease his suffering with sacrifices, or they're a group who try to perform a ritual to communicate with a prisoner. Many of them are incredibly ancient, and know dark secrets which they are willing to share - for a price.
Batman: Arkham City: The titular prison is an interesting example: Inmates are dumped into the Gotham Slums and allowed to do anything they want if they don't try to escape. If they do, the guards are authorized to kill them.
The Gothic game series features one in the first game mixed with Penal Colony. The prison is the magic barrier that surrounds the penal colony, but inside the colony you can do whatever you want. However, in keeping with the trope, the barrier makes escape impossible, and the whole point of the game is try and find a way past the magic walls.
Skies of Arcadia has the Valuan Grand Fortress. It consists of a mountain high stone wall (that is at least 30 yards thick) that has hundred of canons mounted on one side. The stone wall can revolve so it can shoot at either side and there are multiple ports on the inside that can allow an armada of airships to pour out and attack. How do the protagonists respond to such a threat? Escape. For good measure they do it twice.
Hellana Prison in The Legend of Dragoon, which the main characters visits twice to save two characters. And both times, the boss of the area doesn't get a chance to chop your head off.
Corel Prison in Final Fantasy VIIcan be escaped from...the problem is, it's in the middle of an endless desert and you'd probably die of thirst before you made it out. The desert has quicksand too.
The D-District Prison in Final Fantasy VIII is pretty hard to escape from, given that it sics guards with Sleep spell training on you, lots of monsters and mechs of varying types, has powerful anti magic barriers, and requires heavy machinery to even reach certain parts of the place. (The main body of the prison is actually three giant vertical screws, allowing it to dig into and out of the sand.) Like Corel prison, it is also in the middle of a desert - so even if the prisoner escapes, without any way of getting back safely, they're not going to be surviving.
Final Fantasy X has Via Purifico, an underground labyrinth that even requires swimming to get anywhere. It can be escaped...but there's only one exit, so it's not exactly tough to guard and kill any survivors that make it out.
World of Warcraft has one of these in the Instanced dungeon The Arcatraz. It requires a fairly lengthy quest just to get the key to open the place. However, once inside you find out that the warden was enslaved by the monster from the deepest cells and has unleashed everything. The final encounter said warden unleashing five Sealed Evil in a Can on the party, the fifth one being the monster that kills him right away. Well, he calls down four technically. He builds up the Second to be a Sealed Evil in a Can , but he turns out to be an Innocent Bystander Gnome Mage who'll help you fight after a minute or so. The guy later reappears to be fully evil too.
Minera Prison Island from Castlevania: Order of Ecclesia was once a prison populated by petty thieves and criminals long forgotten by society. Now it's just a breeding ground for demons and other horrors, as well as the Wake-Up Call Boss that can easily dispatch Shanoa in a few hits.
During the events of Silent Hill 2, James gets to visit the remains of the Toluca Prison localed beneath the Silent Hill Historial Society.
The San Francisco Rush series of Driving Games has, in every single installment barring the original arcade version, a course that is set on Alcatraz. Alcatraz in-game looks much bigger than its real-life counterpart.
Mass Effect 2 has Purgatory, a prison-ship run by a group of mercenaries that is half a legitimate business and half a kind of protection racket. They take the worst of the galaxies worst and keep them in seperate cells that can be vented to space, or they can just dump entire cell blocks when things get too bad. This is of course extremely expensive and requires that everyone who sends their most dangerous criminals they can't execute for some reason has to pay a regular fee. If the governments don't pay, the prisoners will be released. And get a free ticket back to their homeworld. Alternatively, the Warden is more than happy to sell prisoners to anyone who can pay more than he makes from the maintenance fees.
Butcher Bay from Escape from Butcher Bay is a triple-max security prison facility built on a barren desert planet. The point of this place is that you don't leave. Its highest security level is especially bad; the prisoners are kept in cryogenic sleep inside vats (prolonged contact to which seems to have damaging effects on one's psyche and/or mental abilities), and are only awakened for exercise five minutes per day. Riddick finds an exploitable flaw in the system and gets out.
In Final Fantasy Crystal Chronicles: Crystal Bearers, there is the Aerial Prison. a giant prison compound filled with deadly guard robots, laser defenses, etc. But the worst part is the fact that it is floating in the sky, at such a height that jumping off would kill you. if you do manage to escape your cell, dodge the guard 'bots, make it outside, and somehow get to the ground without dying (our heroes ended up crashing the entire prison to get to the ground), all you've managed to do is land yourself in the Prison Sands, another desert-based prison located directly beneath.
The Gulag in Modern Warfare 2. The player character has to go there at one point to break out one specific prisoner.
Prison Island from Sonic Adventure 2 is based off of Alcatraz. No fewer than three characters are trapped there over the course of the story.
An old Xbox game called Prisoner of War has the character escape from five German prison camps from WWII, including Stalag Luft and Colditz Castle (see Real Life below). While foiling a Nazi rocket program at the same time. In fact, he escapes from the fourth prison camp, just so he can go to the fifth! Guy is a damn Houdini.
New Folsom in Starcraft II is this. Siege tanks, Ravens, ghosts, and more marines and marauders than you'll ever need guarding the Terran Dominion's political prisoners and an assortment of other galactic plagues, and it only took fifty years since its founding for Raynor's Raiders, with help from rogue Spectre Gabriel Tosh, to thwart its security measures.
Raynor: Damn, Nova must've tipped them off. We'll need an army to break inside. Tosh: Even an army can't break through. But one man - one Spectre in the right place - can find a way in.
It's never actually seen in Dragon Age, but the Mage PC Origin and a codex entry reference The Aeonar, a prison run by the Chantry. Apostate mages and maleficars and their conspirators are sent here. This trope doesn't apply to any prisons actually seen in the game, as the ease at which you escape or free others from them suggest they're somewhat more fragile.
"The Gallows" from the second game swings between being one of these and a Cardboard Prison. For the first half of the game, the Mage Underground performs numerous prison breaks, with sympathetic Templars either aiding or chosing to turn a blind eye. By Act III however it becomes a full on Alcatraz as the Templars crack down on sympathisers, the Mage Underground is completely obliterated and the Right of Tranquility performed on Mages for the slightest infractions.
Bargate Prison in the Fable games, which you have to escape from after being captured in the first. Then there's the Spire in the second game, where you've been as a guard for ten years trying to rescue a character. You then fight your way past legions of guards and sail a ship out of the Spire back to the mainland.
In Destroy All Humans! 2, the expy of San Francisco level has an expy of Alcatraz just off the shore called The Rock. At the time it is used as the secret base for the KGB.
In Infinite Space, the planet Skantzoura in the SMC and Lari and Belgirate in the LMC are used to imprison dangerous criminals and the politically inconvenient.
Nova Prospekt in Half-Life 2 Before the Seven Hour War, Eastern European prison. Once The Combine took over it became a much worse place.
The first level of Bomberman 64: The Second Attack is called "Lost Planet Alcatraz". It's about what you'd expect from a name like that.
Sly 2: Band Of Thieves has Sly and Murray thrown into one of these in the 4th chapter at the hands of The Contessa. The only way for them to break out is for Bentley to break in.
The protagonist must ecape from one of these in the first mission of Saints Row 2.
The Elder Scrolls V: Skyrim has Cidhna Mine. You can escape from every other prison in the game, but not from this one, without outside help. The only possible escape route becomes available when you act as outside help to the local Rebel Leader imprisoned within (or by killing him and looting his body for the key), and it works only once, so you can't use it youself if you land in Cidhna Mine later.
The Winterhold prison is no slouch either. It is obviously inspired by Azkaban, which is natural, given that Winterhold is a mage city; it is located on an arctic island and guarded by ice elementals. In normal game, once you slip past the elementals, you can swim to the shore; if you have a realistic hypothermia mod installed, this prison becomes no less an Alcatraz than Cidhna Mine.
Morrowind features the Ministry of Truth, which is a small moon floating over the Temple Canton of Vivec City (meaning you have to have some means of flight just to reach the prison). The Temple uses it to imprison dissident priests and religious criminals (the interpretation of this is deliberately vague, and in fact one of the Dissident Priests' charges against the mainstream Temple). You never have to escape from imprisonment in it, but one of the main quests has you break an ally out of it (fortunately, this only requires getting in — you aren't expected to actually lead your ally out, just hand her a scroll allowing her to teleport away (prisoners have their magic drained and aren't allowed to keep scrolls, and the guards are religious fanatics, thus why this method doesn't work for prisoners without outside aid) and then use another copy of the scroll to follow her). This can turn the prison into something of a Cardboard Prison if you have become the Patriarch of the Temple, as you can simply walk in and ask for keys and directions. There are a few guards that are still hostile, but you are warned about them when you get the keys.
Ultima V takes place after Lord British has been captured by the Shadowlords. So let's see, they trapped Lord British inside of a mirror inside of a room that's on a ridiculously secure floor at the bottom of a very dangerous dungeon filled with monsters and puzzles, which is filled with barriers that can only be brought down with one of the crown jewels that was taken from him, you can't even set foot in the dungeon without the very last Word of Power which you don't get until all eight Sacred Quests are completed, the Shadowlords themselves show up to defeat the Avatar if he manages to set foot in that dungeon before defeating all three of them, the dungeon entrance itself is cloaked in darkness that can't be penetrated without another of Lord British's crown jewels, the darkness itself is hidden behind lava and mountains that can't be crossed without losing hit points, in a section of an underworld that lies beneath yet another dungeon which is less dangerous, but is also sealed up with yet another Word of Power, and everything that could have gotten Lord British out of there was either taken from him and hidden, or left in his private chambers? Yeah, I think it's safe to say the Shadowlords really, really didn't want Lord British to escape.
The main setting of Indie game Escape Goat is the Prison of Augus, where the goat protagonist is sent to for the crime of witchcraft.
In Kingdom Hearts II, the final Disney world of the game, Space Paranoids, starts off as a prison. While the world's pit cells are escapable for Keyblade welders and their allies, there is still the matter of being trapped inside the world itself whenever the computer is turned off. It only took turning it back on from the inside that the world loses it's prison status.
Robopon 2 has Gust Prison. Cody only escapes with the help of time travel.
Might and Magic X features Fort Laegaire in the The Falcon & the Unicorn DLC. Named for Laegaire the Mad, the Emperor of the Holy Falcon Empire who commissioned the prison, Fort Laegaire is located on a small island far out at sea (too far for any non-amphibious being to swim to shore from), has its wall enchanted so that magic can't pass out of them (stopping magical calls for help. The fort has a balcony which is open enough to not be subject to that, but the only entrance to it is from the commandant's office), and features an extensive aerial defence system, stopping anyone from approaching or leaving via air. The prison function was supposedly abandoned after Laegaire's death, with the fort later re-purposed as a base for anti-piracy operations by the Unicorn Duchy, but in actually the Duke of Unicorn has maintained it as a prison, using it to dump any people he wants or needs to 'disappear' without such pesky things as trials. It would still be a proper Alcatraz, but is compromised by the guards being corrupt and/or dissatisfied with what is going on. Combine that with your characters being imprisoned after beating the main game...
Star Trek Online has Facility 4028, a prison for the most dangerous criminals in the entire Federation. The prison is built into an airless planetoid and staffed almost entirely by holographic personnel, with individualized security approaches for every inmate. Inmates include a Cardassian True Way terrorist convicted of war crimes, an Undine who had impersonated a Starfleet captain in the backstory, and the female Changeling.
Girl Genius's Castle Heterodyne is a sentient (if badly damaged) psychopath's funhouse filled with deathtraps and run by an insane and fragmented AI. (It's also the titular heroines' ancestral home.) The ever-pragmatic Baron Wulfenbach deals with troublemakers by sentencing them to join the repair crew, thus killing two birds with one stone.
In one of the most terrifying Lets Plays out there, The Terrible Secret Of Animal Crossing, the town to which the hero is sent to is not an adorable land of fuzzy morons. It is in fact an inescapable prison that slowly turns humans into animals, who are then used as replacement parts for the insane warden. And it's awesome!
In the Whateley Universe, the Red and Black Sections of ARC (the Arkham Research Consortium) are used as uncrackable prisons to hold people and things too dangerous to ever let loose. When Fey, Carmilla, and Bladedancer go to ARC (knowing from a seer that the day will be a good day to try to help Carmilla's friend Merry break out), they find out why: a villain has set timers so that a horrific supervillain will be able to escape on that day.
So the horrific supervillain doesn't actually escape, and Merry only gets away with the help of the head of Red Section!
Plus Roxbury C, the Massachusetts facility for supervillains, set 70 feet underground in solid bedrock and magically warded. It had never been cracked at the start of "Ayla and the Boston Brawl."
Roxbury C's 'inescapable' status was, naturally, a lead-up to the inevitable - there were a million ways to keep prisoners from escaping, but one too few protections against an unauthorized party getting in, as they found out in Ayla and the Birthday Brawl.
Tech Infantry has the Federation (and later Imperial) Prison in the R45 systiem is a Death World and prison planet from which escape (or even survival) is almost impossible. Orbital forts and warships in orbit to prevent rescue, powerful magical incantations and a natural anti-magic field to prevent magical teleportation escapes, and a toxic ecosystem overrun by insane stranded Bugs make it a not at all nice place to be sentenced.
The Birdcage in Worm. It's a prison fitted into a mountain where a hole in a wall creates a deadly vacuum. It is designed to have people go in and never come out. So far, it has been sucessful. As there are no guards in the Birdcage, it's basically run entirly by the supervillains contained within, and so while supplies are sent in, it's also a Hellhole Prison.
The Fire Nation keeps captive Earthbenders on a giant steel platform way out to sea. The lack of anything to practice on keeps the prisoners down, even when Katara makes a Rousing Speech, until the others grab a huge load of coal, which the Earthbenders can work with. One of the reasons the movie was so disliked was that they dropped the "out to sea" part, keeping the Earthbenders in a quarry.
The Boiling Rock is one of the most over-the-top examples that isn't for humor: It's a maximum security prison, on a tiny island, in a lake heated to boiling by hydrothermal vents, in the caldera of a remote volcanic island, so that the only way in or out is an aerial tram to the docks. Sokka and Zuko break out Suki, Hakoda, and a random inmate named Chit Sang ("Hey, I'm new").
Early in Book 3 of The Legend of Korra, the four members of the Red Lotus get one of these each. Each one is tailor made to restrict their abilities. They worked for over 15 years and even then they only failed because their leader gained Air Bending through what was basically a miracle.
Belle Reve in Young Justice is a supermax facility located in the Louisana bayou, and built to house most it not all of the strongest and deadliest of super villains. The only thing keeping all the inmates at bay are special collars designed to negate their individual powers, and shock them into submission if they break the rules. Then somebody figured out having the baddest villains under the same roof was a plus, so the evil cabal known as the "Light" engineers an failed escape attempt, (by having ice-based villains purposly caught and brought to Belle Reve to freeze the walls solid and smash through them), that allows one of their agents to be put in charge of the facility. Despite all the major villains being unable to escape, Edward Nygma, aka "The Riddler", is the only one that manages to break out during the ice-villains' attempt, after being harrassed for so long, and called a loser and second-rate criminal.
Superjail, from the series of the same name, seems almost ridiculously inescapable. For one thing, it's on top of a volcano... which apparently grew right in the middle of another volcano (so, you know, lava moat), which is on a desert island and it's probably in another dimension. One character manages to escape by the end of the first episode. It's a good thing too; in Superjail, you go in... and that's about it.
This soon proves to be a running gag that occurs Once an Episode, where by some strange coincidence he manages to escape at the end of every episode only to be brought back at the beginning on the next one.
Walker's prison stronghold in Danny Phantom. Naturally the main character got all the Rogues Gallery he's faced so far to help create havoc and escape. All this for a present.
In the Dungeons & Dragons cartoon, Venger's "Prison of Agony" is an enormous prison suspended over a lava lake in a volcano by four enormous chains. One of the biggest reasons it was escape-proof was because the winch to operate the drawbridge that was the only way in or out was so heavy, only the giant who guarded it could turn it. The giant actually wasn't a bad guy; Venger was blackmailing him by threatening to destroy his homeworld. (Apparently, he was in the same situation as the heroes.) Naturally, when Venger sent the heroes to this awful place, the giant proved a valuable ally when they launched a mass-jailbreak and destroyed the whole facility.
Then there's prison 42: a prison designed by Ant-Man, Reed Richards, and Iron Man later in the series. This prison is based off the Negative Zone prison mentioned in the Comic Books section, and much more like a more traditional alcatrez. The only entrance is through the Baxter Building, and that entrence is key card and hand scanner protected. Each cell is protected by a transparent forcefield, and since the prison is in the negative zone, they can lock the door if anyone tries to break out (nobody has yet). It used to be patrolled by hundreds of Ultron robots, but after their destruction in the war against Kang, it currently is under SHIELD control with hundreds of armed agents patrolling at all times. Thus far, it has proved its worth, as no villain who ends up in the negative zone has ever escaped (yet).
42 was ultimately retired when the Annihilus revealed himself and nearly destroyed the prison, endangering prisoners, guards, and the outside world.
Storm Hawks has the Cyclonian prison on Terra Zartacla. Since the actual prison complex is surrounded by a dense jungle, escaping the prison proper doesn't mean you're home free. What's more, the warden, Mr. Moss keeps dangerous animals bred for tracking down escapees. And since a 'terra' in Storm Hawks means a tall peak surrounded by a volcanic wasteland, without a pre-arranged ride you'd be out of luck. Aerrow manages to escape, and spends the episode dodging Mr. Moss' forces until his friends who by this time have freed the rest of the prison while it was left defenseless because Moss called all of his men on the search.
The Citadel in Star Wars: The Clone Wars can be found on a remote volcanic planet, blockaded by the Separatist fleet. It's explicitly stated, that even if someone manages to escape the institute, they still can't really go anywhere because the landscape is almost impossible to cross -esspecially while being chased.
W.I.T.C.H. has the prison of Cavigor where Prince Phobos sends rebels and anyone else that opposes him. It's a lot like the original Alcatraz only instead of water there's a Bottomless Pit and there's only one way in or out; Caleb states that even the guards are prisoners until they're relieved by the next shift. Cavigor was in the original comics, but was just a regular prison on a hill. Both versions have giant cockroaches as guard dogs, just to add to the charm.
A weird example occurred in one Huckleberry Hound cartoon. Huckleberry was the warden of a prison in the middle of nowhere, from which nobody escaped...because the amusement parks and various entertainments inside made the place so darn fun. In fact, Huckleberry's problem in that cartoon wasn't a criminal trying to break out, it was one who'd served his sentence trying to break back in.
In Winx Club, the frozen prison planet of the Omega Dimension is where the most evil criminals are sent. Anyone sent there is either frozen or placed in a capsule and then shot down to the surface from space. Anyone that gets out must deal with large ice snakes with an ice breath that can freeze lightning, freezing to death, finding any food and supplies, and avoiding roaming gangs attacking intruders. Without a spaceship, the only way out is a single portal heavily reinforced with magic. Anyone who could get through that would arrive on the ocean planet of Andros and be confronted by the mermaid guards at the portal. When the Trix are sent there, they free another prisoner, Valtor. They locate the portal and manage to break it open while simultaneously brainwashing the mermaid guards. They then stroll free, leaving the portal open for other prisoners to escape.
In SilverHawks, the Penal Planet serves this purpose. Mon*Star broke out in the first episode thanks to a burst of light from the Moon*Star of Limbo which transforms Mon*Star and gives him the strength to break free.
The Trope Namer is Alcatraz, the famous prison in San Francisco Bay set out on a rock. The most successful escape attempt was a man (John K Giles - a pretty awesome guy in his own right) who stole an Army uniform, snuck onto an Army laundry boat, and took it to Angel Island (another island in San Francisco Bay) where he was immediately apprehended. It says something that this is considered successful.
This trope is so famous that, in direct competition with the 140.6 mile Iron Man endurance triathlon, San Francisco now holds an Escape from Alcatraz triathalon, which starts with the athletes diving off the prison island and swimming to shore, before completing a bike race and foot race.
Ironically, as of 2012 Alcatraz itself has spent more years as a tourist attraction (40 years, 1972 to 2012) than as a federal prison (29, from 1934 to 1963).
The prison (and escape) in The Great Escape was based off a real one, Stalag Luft III.
While somewhat more famous in Britain, Colditz Castle was another 'inescapable' WWII POW camp. The population was composed entirely of men who had already escaped from other prisons and 15 managed to escape even here (there was a 16th who got out, but he wasn't heard from again).
Yet Henri Charrière, according to the novel and film Papillon managed to escape from there.
Giacomo Casanova (yes, the Trope Namer) managed to escape from the supposedly inescapable Doge's Palace.
Arguably, all of West Berlin. East Germany spent enormous amounts of money to keep people from breaking in.
The entire GDR probably fits this trope even better. With an over 1300 km long border, complete with cleared death zones and spring guns, guarded by a 50,000 man strong paramilitary unit, all of it only to stop people from leaving the country.
The British prison on the Rock of Gibraltar.
Portlaois Prison in the Republic of Ireland contains Ireland's most dangerous criminals, members of dangerous drug gangs and criminals serving life sentences for serious crime. A number of Irish Republican prisoners are still in the old E Block. Anyone charged under Section 30 of the Offences Against the State Act must be sent to the prison because of its unique security measures.The prison has a capacity for 399 prisoners, but because of the security sensitive nature of its inmates, it operates below this capacity. A large number of well armed Irish Defence Forces soldiers guard the prison 24 hours a day, making it one of the most secure prisons in Europe.The security features include a army detachment consisting of approx Company strength, armed with assault rifles and anti-aircraft machine guns, who guard the prison complex. An air exclusion zone operates over the entire complex. The perimeter consists of high walls, cameras, sensors and acres of tank traps.
Elba was supposed to be this for Napoleon. Despite being an island guarded by the British Navy, he managed to escape after 300 days. After Waterloo, he was exiled to Saint Helena, a barren and isolated chunk of rock in the South Atlantic. He didn't escape that time.
Australia was a penal (prison) colony for Britain for the greater part of the 19th century, and well beyond swimming distance to someplace better, and certaintly prohibitively far from England, which was the point. On top of that, it's Austrailia, Everything Is Trying to Kill You is in effect for the best part of the continent.
The Marias Islands in Mexico.
During World War II, Nazi Concentration camps were a subversion, as they were neither escape-proof, nor sneak-proof. Alongside people who smuggled various objects inside, who spied and relayed some bits of info to partisans or Allied spies, who helped some prisoners to escape, the prisoners themselves were usually taken out for forced labor in quarries, construction sites or armament factories. The secrecy of The Holocaust was not maintained by guarding those living inside, but by exterminating most of the new arrivals in the first three hours after disembarking from trains.
In federal Supermax prisons, inmates are allowed out of their cell for only one hour a day and otherwise are kept in solitary confinement, being fed through a slot in their cell door. The escape rate from these facilities is virtually zero.
Her Majesty's Prison Peterhead was described as "Scotland's gulag." It is an old, Victorian era building, initially serving prisoners doing hard labour. It only got electricity in 2005, and still doesn't have flush toilets for prisoners.
Spike Island was this when it was used as a prison. In 1985, a riot occured culminating in the prisoners burning down one of the prison blocks. Of course, they were all rounded up, as getting off the island without a boat was impossible.
Several in Russia, such as White Swan (in Solikamsk), Black Dolphin (in Sol Iletsk), Fire Island (in Vologda Oblast). These supermaxes were built for vory, Chechen terrorists and similar especially dangerous criminals sentenced to lifetime imprisonment.
Another one, infamous in Mafiya and gopnik circles, is the Vladimir Central. There is a shanson song dedicated to it.
Note that Russian supermaxes are either from the Tsarist times (like the Vladimir Central) or recently built. The Soviets did not believe in this trope, using either lax but very distant, frozen penal colonies or the death penalty.
Camp Delta, more commonly - and inaccurately - referred to as Guantanamo Bay in Cuba. This houses some of the most dangerous prisoners taken by American forces during The War on Terror (and, by many accounts, quite a few innocent mugs who were in the wrong place at the wrong time). There are 12 guards for every one prisoner, and torture was performed regularly until 2008. Escape is considered virtually impossible; even then, an escaped prisoner would find himself in the middle of a US Navy base and having to cross the heavily guarded border with Cuba or swim across the Florida Straits to...America.
Tadmor Military Prison in Syria, home of rebels and political dissidents. The prison can only be accessed through a single long tunnel, through which those wishing to get in must crawl. During the 1980s, it was infamous as somewhere the regime cast people too important to execute but too dangerous to release - it was nothing more than a hole for them to die in. Closed during the 1990s, it has now been re-opened to hold rebel prisoners taken in the ongoing Syrian Civil War.