"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."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.
— Colonel Von Luger, The Great Escape
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Anime And Manga
- Gunther Milch from Monster escaped twelve times prior to when he was introduced.
- 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 aka Part 4 aka 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.
- From the Batman comics:
- 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 Dalton Brothers from Lucky Luke are this in most of the stories their appear in. They are best known for being Tunnel King but they have tried quite a few other methods as well: cut through the jars at the window with a file, use a broken file to make four extra doors (one for each brother) in the cell, make a hole in the wall with either dynamite or with their mattocks, set the prison on fire, hiding in the wagon with food (comic) of dirty clothes (cartoon)... In fact this have 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 easy it is for them.
- Melvin Mole in the MAD 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 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 (AKA "Big X") is the best organizer of escape attempts among them.
- 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.
- Frank Morris in Escape from Alcatraz.
- 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.
- 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.
- 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.)
- 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
- The Space Precinct episode "Two Against The Rock" featured a psychic alien Prison Escape Artist, who was rather inconspicuously named Houdini.
- 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!"
- Parodied with Major Errol Phipps in the Ripping Yarns episode "Escape from Stalag Luft 112B".
- Michael Scofield from Prison Break.
- 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.
- 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.
- 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.
- Neal Caffery, when he isn't working with the FBI seems to consider prison terms optional.
- 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.
- 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.
- Anne from Dubloon mentions that she has experience breaking out of jail before offering to help Russel break out in the beginning.
- 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.
- 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...
- Jacknife is imprisoned at the start of every episode of Superjail!, and every episode he escapes at the end.
- 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. As despite what prison officials said (that he and his two co-escapees drowned) they Never Found the Body, we can only assume that he's gone straight and is living a normal life under an assumed name... assuming he's still alive, that is (he did escape in June 1962, after all).
- Evidence appeared on early 2016 that showed they made it (whether he and the Algins are still alive is a different story).
- 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 Philipines 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 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.