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Loony Laws

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By royal decree, all citizens of the realm must make their clothing out of taffy and stand on their heads three times a day! Mondays have been outlawed! The color puce is an abomination!
In other words, this is when the lawmakers have gone insane. The usual result of your more literal cases of With Great Power Comes Great Insanity. Might have been written by The Caligula, or put up by the Hanging Judge in a Kangaroo Court. Often Played for Laughs — and is usually Black Comedy even in more serious examples.
Loony laws can also arise from "poison pill" political tactics. Opponents of a sane proposal may add a loony provision in hope of getting the main proposal defeated, but if the proposal passes despite such machinations, the loony provision also becomes law.
Sometimes the law may not have been Loony in and of itself when originally implemented (a law that prevents animal cruelty, for example), but the fact that society changes and Technology Marches On makes any attempt at continuing to enforce the law seem insane (the animal the law was supposed to protect is long extinct, but the law has not been repealed or changed to account for it).
Compare Single-Target Law, where a law passed with a single person in mind ends up affecting people unrelated to it.
May involve a lot of Felony Misdemeanor or Disproportionate Retribution. If the law permits deeds that aren't just wacky but downright wrong, that's Legalized Evil.
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One of the PA announcements in Batman: Arkham Asylum is Joker announcing that while under his control, the asylum has but one rule, the penalty for which is summary execution, with no exceptions. However, he never tells anyone what the rule actually is. It's probably just an excuse for him to shoot anyone he wants on a whim, after which he can retroactively declare that they violated his unstated rule in some unexplained way.
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In El Chapulín Colorado, a retelling of The Brave Little Tailor portrays the King in said story as always making a bunch of ridiculous royal decrees, such as "Rain on Saturdays is forbidden" so he can go hiking.
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The Sam O'Nella Academy video "Weird Laws from Around the World" covers this topic, including a law in Oklahoma against "making an ugly face at a dog".
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The Simpsons:
In "Homer vs. the Eighteenth Amendment", the punishment for disobeying Springfield's prohibition law is to be launched out of the city by catapult. It's right next to another law requiring ducks to wear long pants.
In "The Seven Beer Snitch", Mr. Burns opens a for-profit prison, and conspires with Chief Wiggum to fill it by enforcing bizarre laws. Homer is arrested for kicking an old can in the street five times... because he wasn't accepted for a guard job at the prison he is to serve his sentence in. Another law that makes it unlawful for men to be in public without hats is also mentioned, and they are all printed in a compendium of silly laws.
In "Marge vs. the Monorail," Wiggum discovers that under the terms of the town charter, he's supposed to receive a pig "and two comely lasses of virtue true" every month as chief constable.
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Pawnee of Parks and Recreation has a few of these, partially because they're old and everyone forgot to repeal them, and partially because Pawnee is just odd in general. They have a tradition of throwing a man named Ted into the lake every year, women are supposed to be confined to bathtubs while menstruating, white men can seize any Indian's property for 25 cents, and buffalo can be used as currency.
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Horrible Histories has a sketch about loony "sumptuary laws," which were common in England and Europe historically and dictated clothing you could or couldn't wear based on your station. In this sketch, a man has come to petition Queen Elizabeth I, and keeps receiving lectures that his clothing is illegal before he can actually get his business before the Queen. He has to take his cape off (because it could conceal a sword), remove his shirt (because it's of the wrong material), and put a woolen hat on (to boost the business of the wool merchants.) In the end, Elizabeth asks if there's a law about having "a naked man in my throne room"; apparently, there isn't.note Sumptuary laws also existed in Tsarist Russia: the height of your fur cap was dictated by your status as a noble, as were things like the number of buttons you could wear. Tsar Peter the Great took this seriously and would exile minor nobles to Siberia for getting it wrong.
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Final Fantasy Tactics Advance:
In a case of Gameplay and Story Integration, Judges oversee every battle to ensure that you don't break some arbitrary law that changes every other battle. As the game goes on, the Prince of the Realm suffers something of a Villainous Breakdown and starts decreeing more and more laws. Two laws become active per battle after you destroy the first Crystal, and a third becomes active when you destroy the fourth Crystal and the judges announce their independence.
In a post-game campaign unlocked after completing all 300 requests, Marche learns that Judges and the officials who work for them have been abusing their power to put in all sorts of absurd laws. These include forbidding reading or writing(so the official won't have to do paperwork), banning jumping, preventing people from being at full HP(so people will go around hurting each other to get them into compliance) and requiring people to give free kisses. These laws don't actually affect gameplay, since one official tries to enforce his No Arms law, only to fail.
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On a smaller scale, Weird school rules in Hong Kong discusses the strange rules set up by various schools across Hong Kong through skits, most of which are based on real-life school rules, and some are even based on real-life incidences with a bit of embellishment.
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SCP Foundation: SCP-1434 is a brick that causes the nearest small town to enact and enforce increasingly bizarre laws.
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The Elder Scrolls IV: Oblivion: There are two acts punishable by death in The Shivering Isles — attacking its ruler, Sheogorath, and attempting to grow a beard.
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The Discworld, perhaps predictably, has examples.
Ankh-Morpork has a law against metaphors, once memorably phrased as "if you say someone has a face that can launch a thousand ships, you had better have the passenger manifests." Lord Vetinari is even said to enforce this law from time to time, most noticeably by requiring the creation of the Pork Futures Warehouse, a place to store pork that doesn't exist yet. (Vetinari is entirely sane, but likes to keep other people off balance.)
In Monstrous Regiment, much of Nugganite religion is the very substantive list of Abominations, which now includes babies ("I take it people still make them here?" "Yes, but they feel very guilty about it."), garlic, blue ("The sky is blue!" "Devout Nugganites try not to look at it these days."), rocks, ears, and accordion players, although Vimes for one agrees with him on that last one. Nuggan has actually died because of this. People stopped believing in him as a god, only believing in his Abominations (when people actually wanted something, they pray to the Duchess, who is now a Deity of Human Origin because of it). Since the Disc runs on Clap Your Hands If You Believe, Nuggan withered away until now he's no longer a sapient being; all he can do is Abominate random things, which is the reason most recent Abominations are so ridiculous.
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Jet Lag: The Game: Season zero, Crime Spree, was themed around breaking obscure, unenforced laws around the United States. In season four, this returned as an objective, where you could claim a state by breaking one of the unclaimed laws from Crime Spree. For Michigan, this was "Seduce and debauch an unmarried woman," which was interpreted to mean making a match on Tinder, then getting said match to perform an immoral act — in this case, spreading (obviously false) misinformation.
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Planescape: In Mechanus, the natives are so obsessed with laws that you can be arrested for things like singing in a place where it isn't allowed — at a specific time of day. Regulus, the home of the Modrons, is the worst. An introductory adventure involves the Player Characters being arrested for wearing the wrong color and sentenced to a community service task that will clearly take ten years to do. (If they successfully help the supervisor fight off some invading chaos imps, they can get the sentence reduced to time served.)
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A popular source of convincing-sounding falsehoods and ridiculous-sounding truths in The Unbelievable Truth. Lampshaded by John Finnemore in Series 12, Episode 6, on the subject of guinea pigs (the second one was true):
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The Goblins of Labyrinth establishes that, presumably at some point before its takeover by David Bowie in tight pants, the goblin legislature within the Labyrinth underwent what is known as the "Great Collapse of Good Governance", a period of escalating political inanity that culminated in the appointment of a Prime Minister whose chief qualification for the job is that he is inhabited by the World's Largest Flea (its name is Betsy). The Great Collapse of Good Governance saw the passing of such enlightened legislation as The Law Against Holding Up Any Kind of Lunch Box, the Prevention of Benevolence Act (1451), the Anti-Smirking Laws, the Prevention of Thoughtful Pauses Act, and the Abolition of Death (1896) Act. Reproduction was also outlawed during this period, to no effect.
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Pathfinder: Mayor Barzillai Thrune's decrees at the start of Hell's Rebels include edicts to control rats and stray dogs, mandatory display of the queen's portrait, restrictions on the wear of embroidered clothing, a ban on drinking tea after sunset, and a ban on mint.
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Dungeons & Dragons:
In the adventure X3 Curse of Xanathon, the title curse causes the Duke of Rhoona to proclaim several odd laws, such as "All taxes must be paid in beer", "All riders must sit backwards on their horses" and "Horses can only be fed meat".
Planescape: In Mechanus, the natives are so obsessed with laws that you can be arrested for things like singing in a place where it isn't allowed — at a specific time of day. Regulus, the home of the Modrons, is the worst. An introductory adventure involves the Player Characters being arrested for wearing the wrong color and sentenced to a community service task that will clearly take ten years to do. (If they successfully help the supervisor fight off some invading chaos imps, they can get the sentence reduced to time served.)
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The Kingdom of Khura'in from Phoenix Wright: Ace Attorney – Spirit of Justice has the Defense Culpability Act, which makes it illegal to "support criminals". If you are seen as offering any kind of support or assistance to anyone accused of a crime, and that person is found guilty, then you will be considered guilty of the same crime, and given the same sentence. Since Khura'in's courts are known to hand out death penalties (even against children), the DC Act has essentially resulted in a pogrom against defense attorneys, since "supporting criminals" is pretty much their entire job.
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In Monstrous Regiment, much of Nugganite religion is the very substantive list of Abominations, which now includes babies ("I take it people still make them here?" "Yes, but they feel very guilty about it."), garlic, blue ("The sky is blue!" "Devout Nugganites try not to look at it these days."), rocks, ears, and accordion players, although Vimes for one agrees with him on that last one. Nuggan has actually died because of this. People stopped believing in him as a god, only believing in his Abominations (when people actually wanted something, they pray to the Duchess, who is now a Deity of Human Origin because of it). Since the Disc runs on Clap Your Hands If You Believe, Nuggan withered away until now he's no longer a sapient being; all he can do is Abominate random things, which is the reason most recent Abominations are so ridiculous.
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Alice's Adventures in Wonderland: The Queen of Hearts is defined by being a woman that has to be obeyed on every single little whimsical law she makes on the spot, even the ones that make no sense, and every single crime, no matter how small, all have the same sentence: beheading (thankfully the King pardons everyone when her back is turned, a fact omitted from the Disney version). When Alice first arrives to her kingdom, she meets a group of guards that are rushing to paint every rose on the garden red (they were white), because she just woke up in the morning hating them being white (and made them illegal). During Alice's judgement later on the book, the Queen kept on making things Alice did while defending herself illegal on the spot (and, again, kept calling for her beheading for each transgression).
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The Recess episode "The Rules," appropriately enough, is all about this trope. When Vince and Lawson disagree over whether an errant kickball should be a home run or a strikeout, King Bob sends his lackeys to find a way to settle the matter. They discover a book written by Old King Morty, and Bob insists that everyone on the playground follow Morty's law code. Unfortunately, said code requires them to do things like play basketball with rags and use a tree stump for Four-Square, which leads to mass confusion and chaos. In a rare example of justifying this trope, Gretchen realizes that King Morty reigned during the Great Depression, which meant the kids of his time had to play by rules that encouraged using whatever was on hand, as there wasn't enough money for proper toys. T.J. encourages King Bob to make rules of his own rather than follow ones from a bygone era.
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In Archie Comics, there was once a segment called, "Jughead's Loony Laws", which describes somewhat inane rules in different parts of the world, with the accompanying illustration either showing a Loophole Abuse or parodying how the law is enforced. For example, one law states that a household cannot have more than five cats. The picture shows a man with five mountain lions in his den, telling a cop, "So I've got five cats. What of it?"
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Oglaf:
In the strip "Don't" (pictured above), the town magistrate has to explain to the townsfolk that all the new signs forbidding things like "sex during thunderstorms" and "trimming your beard" aren't loony laws, but loony curses. The community spectre they're stuck with is a spiteful sort. (Interestingly "no trimming your beard" and "no mixing fabrics" are (simplifications of) actual commandments in Judaism.note "No trimming your beard" is a simplification of the commandment not to trim the "corners" of the beard, which gave rise to peyot; "no mixing fibers" is a simplification of the commandment against wearing shatnez, fabric made of a mixture of wool and linen.)
The strip "Assorted Fruits of Wrath" has a crusading army get blown away by its own god for violating a scriptural law about not opening the wrong end of a banana (no mention of which end that is). (Also, as their enemy's commander notes, their religion also prohibits wearing mixed fabrics.)
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The conflict of Santa Claus Is Comin' to Town starts when Burgermeister Meisterburger proclaims a ban on toys after tripping on one and hurting himself. Upon hearing of it, Kris Kringle immediately comments on what a silly law it is. At the end of the special, the narrator explains that once the Meisterburger line died off and fell out of power, the people realized how ridiculous the toy-ban was and repealed it.
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For the Glory of Irk: The Irkens have a lot of weird laws, mostly due to Therron's childishness and Voel's aggravated reactions to it. These include outlawing wearing anything green, outlawing eating anything other than tacos on Taco Tuesday, declaring that the Massive can only fly in straight lines, and requiring a password to change any laws (with the password only being known to the Massive's Employee of the Month).
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Chronicles of Darkness: The Old Laws of the Underworld in Geist: The Sin-Eaters often fall into this, with laws that make no sense, and often contradictory. But you better abide by it, unless you want to run afoul of the Kerberos in charge of the domain...
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In Arthur, King of Time and Space, Arthur in the baseline and space arcs has a tendency to make decrees based on things that annoy him at the time, which sound completely arbitrary out of context. Many of them involve groceries, but one ("No serving of alcohol to cows on a Tuesday") leaves Kay and Mordred deciding they probably don't want to hear the context.
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Gormenghast by Mervyn Peake: Gormenghast has so many strange laws and rituals that by the time someone has become its Earl they are probably quite insane themselves. So the laws and rituals become more insane. Gormenghast is the Crapsack World logical extreme of this trope.
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Judge Dredd: Judge Cal passes a number of ridiculous laws during his insane term as Chief Judge, such as outlawing happiness. Sometimes he gets more creative:
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In the Blackadder the Third episode "Dish and Dishonesty", a number of political parties are running for a certain parliamentary seat in Regency England, including a joke party called the Standing-At-The-Back-Dressed-Stupidly-And-Looking-Stupid Party, along the lines of real-life troll candidates like the Rhino Party or Vermin Supreme. Their candidate, Ivor Biggun, outlines his policy thus:
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My Little Pony: Friendship Is Magic:
Chancellor Puddinghead may have been responsible for a few; according to the Equestria Girls special Forgotten Friendship, she tried to pass a law mandating earth ponies to drink carrot juice at every meal.
In "The Lost Treasure of Griffonstone", there is a "No Singing" sign next to the ancient library in Griffonstone, for no explained reason. This causes a serious case of culture shock for Pinkie Pie, since ponies like her have the habit of busting into song at the drop of a hat.
In "The Parent Map", while trying to find the source of the friendship problem, Firelight mentions an old law that forbids the citizens of Sire's Hollow to prance or canter after dinnertime.
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Henry Danger: "Christmas Danger" reveals Swellview has a book of rather stupid and insane rules which consider certain mundane things illegal, such as not wearing a hairnet when serving food, taking a picture of a rabbit without a permit, eating hard ice cream on a cone, and wearing more than one hat at a time. "Secret Room" also reveals it's illegal to drop a single bit of soup on the floor, even if it's an accident.
Regarding the "Secret Room" soup, it was a bribe so that Piper could get out of going to jail. The police officers merely told her she couldn't spill a single drop just to punish her.
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In Marvel Adventures: Super Heroes #9, Dormammu reveals that the Ancient One forced him to sign a contract upon his first defeat that stipulated, among other things, that he was only allowed to summon his Mindless Ones if he was standing next to a red convertible. Dormammu uses Loophole Abuse by converting most of the cars in the street to red convertibles, but cannot transform a green truck, because it is parked next to a mailbox, and the contract also forbids him from affecting any object ten feet from a mailbox.note More rules that Dormammu must abide by are that he can only enter the human world by taking the form of a rodent, cannot teleport inside a ballerina's house, is not allowed to dry-clean his clothes, is only allowed to eat hot dogs on a Wednesday, can't wear green shoes with black shoelaces, cannot cast spells while dressed as a schoolgirl...
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Nier: The inhabitants of Facade, the People of the Mask, have this as their societal hat. They have over 120,000 rules for seemingly everything, and follow them religiously. Some of the rules are reasonable ("Always repay your debts"), but most of them are incredibly silly and arbitrary ("Never build on level ground", "No one may buy from shops until they have taken a tour of the city", and so on). Still, the People of the Mask hold these rules in deep reverence, so the protagonists generally try to respect them, however exasperating they get.
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The post-apocalyptic New Quahog in Family Guy was briefly ruled by Peter, who, among other things, randomly assigned duties from a "job hat" and not based on expertise.
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Captain Underpants: In a comic they make about Melvin in the sixth book, he becomes mayor and passes countless ridiculous laws, jailing people for things like "stopping to smell the roses" and "reading signs" (that the rules are written on).
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Harry Potter and the Order of the Phoenix: Umbridge is a tyrant in both book and film, but the book only featured 28 Educational Decrees and only seven of them appeared. In the film, they numbered at more than 100 and ran the gamut from "Students performing prohibited incantations will be subject to SEVERE punishment." to "Exploding bon-bons are no longer permitted to explode. Hand in immediately to Ministry disposal unit."
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Bananas: When Esposito's revolution takes the capital, he makes clear with his first official address as President that he will be a worse Caligula than the guy he just deposed by unleashing a bunch of these laws. Esposito's CIA backers immediately drag him away and install Fielding Mellish in his stead.
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The Unstoppable Yellow Yeti: Winterton has very strange laws. For example, you MUST know how to ski if you want to live there.
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In Crusader Kings II, one of several random events that can happen with a ruler with the Lunatic trait is to pass one of four insane laws: either banning the wearing of pants, decreeing that all dwellings must have holes in two opposite exterior walls, declaring turnips the sole currency of the realm, or banning interpersonal violence and capital punishment. None of the laws have any gameplay effect other than the ruler in question incurring an opinion malus with all their vassals.
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Gravity Falls:
The titular town was founded by (ex-) President Quentin Trembley, and his lunacy was reflected with such things as a law that allowed humans to marry woodpeckers.
In the first season finale, Gideon steals the deed to the Mystery Shack, and is instantly recognized as its legal owner. The show's creator jokingly suggested Gravity Falls has a "Finders Keepers" Law where physically possessing an object immediately makes you its rightful owner, even if it was obviously stolen.note In the actual show Gideon claimed Stan gave him the deed, and was just so well-liked the police believed this despite no evidence or reason Stan would do so.
In the second season there's a mayoral election, the qualifications for candidacy being "anyone who can cast a shadow, count to ten, and throw their hat into the ring (literally)". Then the citizens vote by tossing birdseed at their preferred candidate during their final debate, at the end of which a bald eagle is released which then lands on and kisses the victor. Oddly after Stan wins he gets disqualified due to his lengthy criminal record and the new mayor is Tyler Cutebiker, the one candidate who filled out the paperwork properly.
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One case from the sitcom Night Court involves a Yugoslavian husband and wife facing trial for unlawful detonation of poultry.
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