Prison Escape Artist

"This man, Ashley-Pitt, for example. Caught in the North Sea, escaped, recaptured, escaped, recaptured. Archibald "Archie" Ives: eleven escape attempts. Even tried to jump out of the truck coming here. Dickes, William. Known to have participated in digging of eleven escape tunnels. Flight Lieutenant Willinski: four escapes. MacDonald: nine. Hendley, the American: five. Haynes: four. Sedgwick: seven. The list is almost endless... One man here has made seventeen attempted escapes."

— Colonel Von Luger, The Great Escape

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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Examples:

Anime & Manga

• 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.
• 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.
• Gunther Milch from Monster escaped twelve times prior to when he was introduced.

Comic Books

• 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.
• 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.
• 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.
• Wonder Woman Vol. 2: Cheshire escapes from prison with a short length of twine, a cheap plastic knife, and a small compact mirror.
• 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.

Comic Strips

• 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.
• 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.

Fan Works

• Danganronpa: Memento Mori: Ren Kurusu earned his title as the Ultimate Inmate for breaking out of several prisons.

Films — Live-Action

• 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.
• 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.
• 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.
• 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.
• The Great Escape, the Film of the Book based on the Real Life event. The inhabitants of the Nazi prison camp are the best escape artists among captured Allied soldiers, and Roger Bartlett (a.k.a. "Big X") is the best organizer of escape attempts among them. When the Gestapo manages to capture most of the escapists, they decide the best solution to the 50 men who made fools of them and may attempt a repeat escape is an open field and an MG-42 (it still fits under "shot while trying to escape").
• 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.
• Escape from Alcatraz: Frank Morris is sent to the supposedly inescapable island prison of Alcatraz after having successfully escaped from several other institutions.
• Ladyhawke starts with the thief Philippe the Mouse escaping from a supposedly inescapable prison.
• 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.
• John Mason in The Rock is said to have escaped from several maximum security prisons, including Alcatraz itself.
• 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.
• In Shanghai Knights, Lin nearly escapes from jail by using her pillows to make it look like she's asleep under her bedsheets, then drops down from the ceiling to attack whoever comes in. This only fails because her brother and Roy are the visitors and she stops to talk to them. Later, she successfully escapes (albeit offscreen) by picking the lock to her cell with a deck of playing cards and climbing down the wall using a mop, fork, and her undergarments.
• 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.
  Scotty: "What are ye standing around for? Do ye not know a jailbreak when ye see one!?"
• 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.)

Literature

• 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.
• Wallace Nussbaum, the "Napoleon of Crime" of Daniel Pinkwater's Snarkout Boys series, breaks out of prison at least once per book and is implied to have done so more times. One book has him escaping from the supposedly inescapable Devil's Island.

Live-Action TV

• 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.
• 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!"
• 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.
• 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.
• 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.
• The Space Precinct episode "Two Against The Rock" featured a psychic alien Prison Escape Artist, who was rather inconspicuously named Houdini.
• White Collar: Neal Caffery, when he isn't working with the FBI seems to consider prison terms optional.

Tabletop Games

• 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.

Video Games

• 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...
• Anne from Dubloon mentions that she has experience breaking out of jail before offering to help Russel break out in the beginning.
• 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.
• 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.

Western Animation

• Jacknife is imprisoned at the start of every episode of Superjail!, and every episode he escapes at the end.

Real Life

• 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.
• Roger Bushell, the man who inspired The Great Escape.
• Steven Jay Russell, as mentioned above.
• Jack Sheppard was a thief in 18th-century London, who was arrested and imprisoned four times, but always escaped. This made him a hero among the poorer classes. (For his final escape, he was shackled, chained to the floor under constant guard, behind six iron-barred doors — and he still escaped!) Eventually, he was caught for a fifth time and hanged, but his high-profile escapes had made him so popular that his arch-nemesis, corrupt and brutal thief-taker general Jonathan Wild, was undermined with the populace and ended up executed himself within a year.
• Patrick "Paddy" Mitchell was the leader of the notorious "Stopwatch Gang" of bank robbers in the 1970s and 1980s. After they were finally caught, he escaped from prison three times in ingenious ways. After his last escape, he hid out in the Philippines for 15 years before returning to the US and being arrested in 1994. He never escaped again and died in prison in 2006.
• Houdini did this as an advertising stunt. A typical example would be him going to a police station, saying "your cell can't hold me". They would lock him in and he would get out and everyone would hear about it and go to his show.
• Ikey Solomon, the (partial) model for Fagin in Oliver Twist.
• As of December 13th, 2014, Danish criminal Brian Bo Larsen had successfully escaped from prison a record 22 times.
• Autistic savant and "Houdini of Florida" Mark DeFriest was arrested on false charges in 1980 brought up by his Wicked Stepmother and sentenced to a few years in prison, but his seven successful escapes resulted in him being upgraded to a life sentence in spite of his mental condition making him incompetent to stand trial. With a combination of training from his late ex-OSS (CIA predecessor) father and his own engineering knowledge, he managed to utilize strategies like navigating through barbed wire, dosing guards with stolen LSD, and even MacGyvering zip guns to intimidate guards with. As of 2022, he remains in prison (for now).
  Mark: If I was a rapist or a murderer, they'd let me out. But I'm the idiot who made them look like idiots.
• Convicted murderer Richard Lee McNair managed to escape from authorities three times in three different decades from three different facilities. In 1988, he escaped from Minot Police station in North Dakota by using lip balm from his pocket as a lubricant to squeeze out of his handcuffs and then running out of the station, leading police on a three-hour foot chase before he was caught. In 1992, he escaped from North Dakota State Penitentiary in Bismarck, North Dakota by crawling through an air duct in an education room until he reached the roof of the building, where he made his way across several more roofs until he dropped down outside the prison wall, earning himself 10 months of freedom before he was apprehended again. Transferred to the Federal Bureau of Prisons after his second escape, he managed to escape from federal prison in Louisiana in 2006. McNair had a job in the prison manufacturing yard repairing old mailbags. He made his escape by constructing a special "escape pod", which he hid himself in on a pallet beneath a pile of mailbags. The pallet was shrink-wrapped with him in it and taken to a warehouse outside the prison, where he cut his way out and escaped as soon as the work crew left. After escaping, McNair was stopped while jogging on railroad tracks by police officer Carl Bordelon. Bordelon had been assigned to look for McNair after the prison authorities discovered he was missing. But amazingly, after a 10-minute interview (which can now be seen on YouTube), Bordelon let him go, completely unaware the person he was talking to was in fact the fugitive he was looking for. After this escape, McNair was able to remain free until October 2007 when he was arrested in Canada by the Royal Canadian Mounted Police and extradited back to the United States.
• An Older Than Print example: future Sassanian (Persian) Shah Kavad I^note father of the more famous Khosrow I Anushiruwaan, the long-time opponent of Eastern Roman (Byzantine) Emperor Justinian I and generally considered the most significant emperor of the Sassanian Empire was placed into the 'Prison of Oblivion' by his uncle, Shah Sukhra. This prison proved to be rather inaccurately named, as he would escape from it, overthrowing his uncle and taking the throne himself. After a revolt among the nobles, Kavad was deposed and put back into the Prison of Oblivion — which continued to be very very bad at containing Kavads, as he swiftly escaped and returned to power.
• Yoshie Shiratori managed to break out of prison four different times, each under increasingly difficult conditions. Most (in)famously, he used miso soup as a tool to escape from his cell by slowly oxidizing the metal grate of his cell until the screws and bolts finally came loose.

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