Trope Talk: Prison Break!

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Who doesn't love a good stock episode? Let's talk about what happens when you take "character doesn't want to be where they currently are" and boil it down to its absolute purest concentrated essence, and all the fun (?) shenanigans that ensue!
Got a favorite or least-favorite prison break? Shout it out in the comments!

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Let's be honest. Despite having the title of "one of the most secure places on Earth", Arkham is basically at this point a one-night motel for Batman's villains...

TetsuShima
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That last point is what makes 2 of the 3 AtLA prison breaks (Boiling Rock and the coal platform) so amazing. If a building is designed for no reason other than to hold people, than flaws in that design are really obvious and break immersion. However, the aforementioned AtLA prisons aren't *just* designed for incarceration - they're also designed to oppress the inmates.
The prison rig is built in the middle of the ocean to make earthbenders feel hopeless. In order to justify being in open water, the prison rig also needs to be strategically useful and self-sufficient; thus, it runs on coal and refuels fire navy ships (which also use coal), which earthbenders can use. Boiling Rock's anti-firebender freezers, which aren't as infallible as they might seem, are exploited in a very clever way as well, and the plan would've absolutely worked if not for Chit Sang making a small, stupid mistake. The gondolas are also necessary for a prison of such convoluted design, and despite being easily defensible, they are nonetheless a weak point that gets exploited - if Azula, Mai, and Ty Lee hadn't been there, there is a decent chance that any issues in the escape would've been easily solvable.
In other words, if you want a prison with baked-in flaws that's still believable, design it with other purposes in mind: strange or convoluted locations to enforce isolation, slave labor, or excessive punishment and oppression. That last one is probably the hardest to exploit unless you're really clever or have worldbuilding loopholes like AtLA, but the other two should be pretty reliable.

GrayVBoat
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Shout out to the show literally titled Prison Break, which had to come up with increasingly dumber reasons for why the protagonists keep getting tossed in increasingly absurd prisons.

SirAsdf
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Ah, if there is a Prison Break Trope Talk, that means we absolutely need dedicated a Heist/Caper Trope Talk.

_imago
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One thing about prison breaks that tends to get overlooked is that routines tend to make people lazy, even security guards. Do something enough times and you'll tend to overlook little things that might tip you off to something being wrong. Some guy you never seen before, says he's new, his badge looks legit, you wave him through. Someone standing around, why would that be fishy, you got more important things to do. Level 3 is usually off limits to anyone but the higher ups, but this person has proper clearance and getting too nosy just leads to more paperwork and Jim will probably chew you out if you wasted all this time for nothing, wave them through.

hannahdawg
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Watching Suki go full Kyoshi Warrior on the Boiling Rock will always be my favorite.

VivaLaDnDLogs
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I absolutely love when the prison break plan is practically non-existent and only works cuz the protagonists are insane. Like, it's not that the prison security has a flaw, it's just that no sane person would EVER try to the recklessly stupid things the protagonists did.

KtheSongbird
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The Henry Stickmin series has a fascinating twist on the outside rescuer. In one of the routes in "Escaping the Complex", Henry gets rescued by the mafia. In the previous game, Henry had beaten the mafia leader, Reginald, leading Henry to take over while Reginald was left as second in command. The only reason Reginald responded to Henry's call for help was so he could personally betray Henry and take back command of the mafia.

valdonchev
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As a wise man once said " if you imprison an adventurer for adventuring then they will meet other adventurers and break out to adventure even more"

jaminjames
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A classic case of the prison break trope comes from the Count of Monte Cristo, where Edmont Dantes is trying to escape the Chateau d'If (I may have spelt that wrong...) along side his teacher and friend through a prolonged attempt to carve out an exit. However, renovation ends up foiling their plans, and Dantes' friend passes away shortly after. However, the passing of this friend gives Dantes an unexpected exit: he's tossed out into the sea, pretending to be his friend's corpse. This plan is markedly dangerous as the Chateau is far from the mainland, and Dantes has no idea if he'll hit rocks instead of water, but the bet pays off, and Dantes successfully escapes. It's a simple and risky plan, but it's fun to see unfold.

Dragonpit
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Tess, Erin, and Falst: Let's break Kendal out of the prison!

Alinua: Let's break the prison.

EPadraigM
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I applaud Red's self control to only use one clip from "The Blue Spirit", her favorite episode of Avatar

gregorysmith
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Missed the part where if the friend on the inside does survive, they become a party member instantly

bigfootstoe
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My favorite meme with prison breaks is the ones that lead to first attempt failure by whoever is outside that usually creates this sort of interaction.
"Are you guys here to rescue me?"
"Nah. We got caught too."

MageKirby
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Andor's prison break arc was some of the best television I had watched in 2022. The suspense, the unique gimmicks, the horror, and the immaculate performances was just perfect.

stingspring
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11:40 Suggesting that the Boiling Rock, a pair of episodes whose only real motivations and effects are based on character relations (Mai's betrayal, Ty Lee's betrayal, Suki X Sokka, Zuko X Mai, Zuko/Sokka bonding experience, Sokka saving his dad), is just an exciting action set piece.

In fact, thinking about it, if it were purely logic based they would have brought Toph, the only member of the Gaang that can bend rocks and metal and has never hesitated to punch a cop.

Edit: The more I think about it, the more interesting this gets. If this was just a strict "prison break" plot, Toph could and would have gotten them in and out completely unhindered in 10 minutes flat. But it's not about that. It's about "saving the jerk who dumped me" and "you should have feared me more" and "my girlfriend turned into the moon" "that's rough, buddy." None of these character moments would have happened if this was just a prison break and Toph broke the prison.

Scarhand
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Weird thought, but a plot where arkham gets an ACTUALLY competent warden that stops the one-at-a-time prison breaks would be nice, maybe even including the entire rogue's gallery teaming up to break out and showing why the one-at-a-time thing is a better option, actually

somepepperonyoutube
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Firefly has an amazing subversion of the "If the plan's explained, it will fail" trope in the episode Trash. They explain the heist plan, it seems to go wrong, but it actually went perfectly according to plan because the group knew one of their members was planning on backstabbing them, so they incorporated it into the real plan.

Frostbite
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You know what's better than prison break, a prison break-in.

TripleAAA
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Impel Down of One Piece is an entire arc focusing around Luffy breaking into and rescuing a person from the world's most secure prison. Amazing arc that sees old villains return and forming temporary alliances.

VivianKurayami