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Prison Escape Artist

 Prison Escape Artist
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 Prison Escape Artist
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Prison Escape Artist
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 Prison Escape Artist
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So you have a convict. They have been caught, and they are going to the slammer. Justice has been served. Right?
If the convict is a Prison Escape Artist, then absolutely not. To them, prisons might as well be made of cardboard. They can wiggle their way out of anything. Yes, even prisons that are supposedly impossible to break out of such as The Alcatraz. If you build a Tailor-Made Prison just for them, it will fail. Several methods can be used to achieve their escapes, including digging their way out, making use of air vents, and having some friends come in disguised as guards, among others.
Needless to say, they often play a role in a Great Escape, and may lend a Wrongly Accused protagonist a hand if they aren't evil and happen to like said protagonist. If they never get caught again, they might organize escape attempts for other prisoners. Compare and contrast Play-Along Prisoner, as a Prison Escape Artist doesn't necessarily have to be able to escape at any time. Some may just seek out opportunities.
Note: This trope is not simply someone who escapes from prison. This is someone who has escaped and/or has helped others escape more than once, either prior to or during the story.
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DBTropes
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Anders from Dragon Age has escaped from the Circle Tower (which is on an island in the middle of a lake and heavily guarded by armed and armored Templars with Anti-Magic) seven times. Of course, he kept getting recaptured, and once spent a year in solitary, but...
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Nova: The one-off villain Abyss is stated to be able to escape from anything and anywhere, no matter how secure. His archenemies, the Luminals, have defeated and imprisoned him countless times, but he always manages to come back. They even try to get rid of him permanently by stuffing him into a power-nullifying containment unit and chucking him into the nothingness at the literal edge of the universe, but we never get to find out if this would have worked.
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Lupin III: The Italian Adventure a.k.a. Part 4 a.k.a. the "Blue Jacket" series, has Lupin willingly get captured by Zenigata in order to spare Rebecca from being caught. He makes multiple attempts at escaping, knowing that Zenigata is there at every turn to beef up security. Eventually, he gets put inside an isolated Tailor-Made Prison that cannot be opened through any means besides Zenigata himself. Lupin acts increasingly depressed, giving up the will to live, and just accepting his fate that he's finally been caught once and for all. He refuses to eat any of the meals that Zenigata cooks up. Zenigata is increasingly worried about his behavior because, under Italian law, he's not allowed to let a prisoner die if there are any ways to prevent it. Eventually, he looks through to the slot in the prison door to see Lupin seemingly dead, and he opens the door to find that he'd been tricked by an elaborate optical illusion that Lupin painted onto the floor using the meals he never ate. Lupin hid in the corner above the door and slipped out, locking up Zenigata in the process, and going about on his way.
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Both Pour Elle, a French thriller about a man attempting to break his wife out of jail and its English-language remake, The Next Three Days, feature one of these characters. In the latter, he's played by Liam Neeson.
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White Collar: Neal Caffery, when he isn't working with the FBI seems to consider prison terms optional.
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In Strange Psychokinetic Strategy, Fujiko needs Lupin's help to escape from jail. He promises to do so in exchange for a date. Of course, just because he's successful doesn't mean that he's going to receive anything nice in repayment. (He gets Mugged for Disguise and left in her prison uniform for the police to capture.)
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Jacknife is imprisoned at the start of every episode of Superjail!, and every episode he escapes at the end.
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The Joker is this among other things. Not only does he often break out of Arkham, he initiated a jailbreak from The Slab during The Last Laugh storyline. In the case of The Slab, no-one had been able to escape from it before. Even when he was put in a room with no entrances or exits, he still escaped... somehow.
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Anne from Dubloon mentions that she has experience breaking out of jail before offering to help Russel break out in the beginning.
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Wonder Woman Vol. 2: Cheshire escapes from prison with a short length of twine, a cheap plastic knife, and a small compact mirror.
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Seven Years in Tibet: Heinrich makes at least four solo escape attempts before joining Peter's and makes it outside the wire at least once.
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Discworld: Terry Pratchett's The Last Continent gives us Tinhead Ned, based loosely on the real-life Ned Kelly and Jack Sheppard. Sir Pterry's Ned was an inveterate sheep thief who kept getting caught, but who kept escaping just before he was hanged. Eventually they stopped locking him up and just hanged him as soon as they caught up with him. But Rincewind learns his secret when he himself is locked in Ned's cell. Not only are the hinges on the inside of the door, but they're simple pin hinges. Any prisoner can just lift the door straight out of the hinges, then slot it back in place once he's out.
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I Love You Phillip Morris is based around Steven Jay Russell, a real-life conman who has escaped prison multiple times in increasingly creative ways.
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MAD: Melvin Mole in the comic story "Mole!" can just dig his way out of any prison, using any digging implement — even if the prison is on an island. He doesn't necessarily emerge in a safe place, though.
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The Space Precinct episode "Two Against The Rock" featured a psychic alien Prison Escape Artist, who was rather inconspicuously named Houdini.
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Batman:
The Spook's original shtick was offering criminals incarceration insurance: promising that he could break them out of any prison if they were caught.
The Joker is this among other things. Not only does he often break out of Arkham, he initiated a jailbreak from The Slab during The Last Laugh storyline. In the case of The Slab, no-one had been able to escape from it before. Even when he was put in a room with no entrances or exits, he still escaped... somehow.
The Riddler is self-trained in escapology and has been shown to easily escape from prisons even other villains can't get out of.
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Lucky Luke: The Dalton Brothers are this in most of the stories they appear in. They are best known for being Tunnel Kings but they have tried quite a few other methods as well: cutting through the bars at the window with a file, using a broken file to make four extra doors (one for each brother) in the cell, making a hole in the wall with either dynamite or with their mattocks, setting the prison on fire, hiding in the wagon with food (comic) of dirty clothes (cartoon)... In fact, this has become so much of a Running Gag, that the creators in some of the later stories will simply just skip the escape part since the readers already know how easy it is for them.
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One of the prisoners, Axel Herrmon, from Traveller Classic adventure 8 Prison Planet has escaped from the Imperial prison facility on Newcomb and another prison as well.
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One Iznogoud story had him hire a master criminal for his latest scheme, and conveniently he heard he was already locked up in the dungeons. Only when Iznogoud went to meet him, no one was in the cell. A guard informed him that they had locked up the thief several times and he always escaped effortlessly, so they've stopped even trying. The thief on his part had taken to also breaking back into his cell whenever he wanted a free place to sleep and get a meal.
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Danganronpa: Memento Mori: Ren Kurusu earned his title as the Ultimate Inmate for breaking out of several prisons.
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Hogan's Heroes:
Hogan and his team break out of Stalag 13 so often that Klink might as well have just given them the keys to the front gate. And then they break back in when they're done with whatever business they had outside the camp because it's in their long-term interests to let the Germans think that they're still locked up.
One episode also has a former stage performer and career Escape Artist intentionally get caught and thrown into Stalag 13 as part of a long-term rep-building ploy to break out of every P.O.W. camp in Germany. This creates a problem for Hogan because Stalag 13's artificial status as The Alcatraz is the only thing keeping the German High Command from replacing Klink with someone far more competent.
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An episode of Murdoch Mysteries has Harry Houdini, expert at escaping anything, escape from jail no less than three times after being a murder suspect.
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Lupin III escapes from prison multiple times.
The second episode of the "Red Jacket" series has him get himself, Jigen, and Goemon locked up to create an alibi for a theft, which meant they would have to break out and in before anyone noticed they were missing.
Lupin III: The Italian Adventure a.k.a. Part 4 a.k.a. the "Blue Jacket" series, has Lupin willingly get captured by Zenigata in order to spare Rebecca from being caught. He makes multiple attempts at escaping, knowing that Zenigata is there at every turn to beef up security. Eventually, he gets put inside an isolated Tailor-Made Prison that cannot be opened through any means besides Zenigata himself. Lupin acts increasingly depressed, giving up the will to live, and just accepting his fate that he's finally been caught once and for all. He refuses to eat any of the meals that Zenigata cooks up. Zenigata is increasingly worried about his behavior because, under Italian law, he's not allowed to let a prisoner die if there are any ways to prevent it. Eventually, he looks through to the slot in the prison door to see Lupin seemingly dead, and he opens the door to find that he'd been tricked by an elaborate optical illusion that Lupin painted onto the floor using the meals he never ate. Lupin hid in the corner above the door and slipped out, locking up Zenigata in the process, and going about on his way.
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The Elder Scrolls: You can be one in Oblivion and Skyrim. In the latter game, there's also one inescapable prison; however, a Rebel Leader imprisoned there is revealed to have a handy escape tunnel, just in case, which makes him another example.
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3:10 to Yuma: It's revealed that Ben Wade has already twice escaped from Yuma prison; he willingly boards the train to Yuma to ensure Dan Evans receives the reward for delivering him, but whistles for his horse as the train pulls out and it's implied that a third escape is coming.
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In Cube, Rennes is a French escape artist known for getting out of jails. Subverted when he triggers a fatal booby trap shortly after he's introduced. There'll be no easy way out of the Cube, folks.
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On Leverage Parker seems to qualify, though only in the backstory. Nate also manages to escape from custody a few times, though once he was never actually imprisoned as he got away beforehand.
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John Mason in The Rock is said to have escaped from several maximum security prisons, including Alcatraz itself.
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The Spook in The Wizard of Id is always escaping, but he's always caught again soon afterwards, usually because his plan backfired on him.
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The Escape Plan series has Ray Breslin as this trope as a prison consultant, first casually going into supermax prisons undercover as a prisoner and then breaking out to show their weaknesses and improve their security, then getting thrown into the movie's The Alcatraz.
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River Song in Doctor Who. In the 2011 series so far, she has been shown exiting and entering Stormcage prison at will, even stopping to pick up a phone and holler over the klaxons, "Oh turn it off, I'm breaking in, not out!"
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Gunther Milch from Monster escaped twelve times prior to when he was introduced.
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Ladyhawke starts with the thief Philippe the Mouse escaping from a supposedly inescapable prison.
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In the postgame of Hades, Hades decides that Zagreus has been so good at escaping the underworld that he's good at exposing flaws in their security, "the kind of flaws that don't show up in reports." Zag is then just hired to do what he's been doing the whole game, in an official capacity.
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Star Trek V: The Final Frontier: The designers of the Enterprise-A had at some point recruited Captain Spock to try to escape from the new brigs installed on the ship. Despite his best efforts Spock failed to escape. Later on Spock, Captain Kirk, and Dr. McCoy are placed in a cell by Sybok's people and initially they are unable to escape either. However the designers had failed to consider the possibility of outside assistance. Kirk, Spock, and McCoy all escape when Montgomery Scott blows a large hole in the back of the brig's cell.
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In an episode of Barney Miller Barney is told by a snitch where an infamous prison escape artist is hiding out. He had been sentenced to 5 years for robbery 30 years earlier, but his sentence kept getting extended because of his frequent breakouts. The escape artist has decided to hang it up; although he does break out of the holding cell in the squadroom at one point in order to use the restroom. Nobody notices until he saunters back and locks himself up again.
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As dramatized in Escape from Alcatraz, Frank Morris is a Real Life example, rendering every single prison he was held in as cardboard, including, you guessed it, Alcatraz. The two men who broke out with him, John and Clarence Anglin, were also known as escape artists (although, like many escape artists, Morris and the Anglins discovered that staying out after escaping is much harder than getting out in the first place, and were always recaptured). Prison authorities think the three men drowned, and there hasn't been a confirmed sighting of any of them since the day they escaped, although some believe they may have survived, citing that their bodies were never found. Their fate remains a matter of debate.
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The Riddler is self-trained in escapology and has been shown to easily escape from prisons even other villains can't get out of.
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Prison Escape Artist
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Diggstown: Gabriel Caine comes across one of these for the short portion of the film he spends in prison, having developed a fool-proof way of breaking out of the prison he's in undetected and using it to break out other prisoners in exchange for money while serving out the rest of his own sentence.
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Roger Bushell, the man who inspired The Great Escape.
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In Golden Kamuy, Abashiri Prison holds Japan's most heinous and dangerous convicts, neither of which are words you could use to describe the "Escape King" Shiraishi Yoshitake. He's a bumbling petty thief who, as his nickname suggests, also happens to be an expert Escape Artist who has broken out of every less secure prison in Hokkaido at least once. Flashbacks have shown some of his previous escapes, with his methods including making a paper-mâché replica of the master key and hiding it inside a beetle shell until he had a chance to get away, and starving himself and dislocating his limbs to squeeze through tight spaces. He even taunts jailers by threatening to escape on their shift if they're not nice to him. Sure enough, when a group of 24 prisoners successfully escape from Abashiri, Shiraishi is among their number, and the heroes make use of his skills when they need to break into Abashiri to meet with one of the prisoners.
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The following is a list of statements referring to the current page from other pages.

 Prison Escape Artist
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Escape Tropes
 Prison Escape Artist
processingCategory2
Prison Tropes
 The Wizard of Id (Comic Strip) / int_3e463af8
type
Prison Escape Artist
 Cube / int_3e463af8
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Prison Escape Artist
 Diggstown / int_3e463af8
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Prison Escape Artist
 I Love You Phillip Morris / int_3e463af8
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Prison Escape Artist
 King Arthur: Legend of the Sword / int_3e463af8
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Prison Escape Artist
 The Great Escape / int_3e463af8
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Prison Escape Artist
 Nanbaka (Manga) / int_3e463af8
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Prison Escape Artist
 Ripping Yarns / int_3e463af8
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Prison Escape Artist
 The Gospel Bill Show / int_3e463af8
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Prison Escape Artist
 Maniac Mansion (Video Game) / int_3e463af8
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Prison Escape Artist
 Papers, Please (Video Game) / int_3e463af8
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Prison Escape Artist
 Choice of Games / Videogame / int_3e463af8
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Prison Escape Artist
 Extra Credits (Web Animation) / int_3e463af8
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Prison Escape Artist
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Prison Escape Artist