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  • In the Ace Attorney Investigations manga, Randolph Miller's three hires to watch over the painting — Monet Kreskin (his niece, who knows nothing about art), Dick Gumshoe (the series's Clueless Detective), and Thomas Bester (a private detective possibly even worse than Gumshoe, but more conceited) — seem to be poor choices, because none of them know much about art, but then it turns out that Randolph sold the painting and wants to both stage its theft and kill Max Arden, the only other one who knows the truth. Then again, the failure of the plan is largely because Gumshoe's involvement brings in the much more competent Edgeworth, rather than any of the three being more competent than Randolph expected.
  • Berserk: This turns out to be the origin of Dragonslayer, Guts's signature BFS. It was created by the smith Godot, as a form of protest when his lord told him to make a sword capable of killing dragons. As he thought the challenge was stupid, because dragons don't exist (well, he thought so, anyway), he proceeded to design and forge an equally stupid weapon. The result was a sword so absurdly massive and heavy that most men couldn't even lift it unassisted, much less use it in a fight. However, as it turned out, when Dragonslayer was put in the hands of a man who was strong enough to use it in a fight, it is a terrifyingly effective weapon, able to shred plate armor and slice through giant monsters.
  • Billionaire Girl: In the last chapter, Yukari tries to lose her money by making investments with higher-than-usual risk. She actually makes a profit.
  • Case Closed has a case where Heiji and Kazuha are arguing over whether to see a baseball game (Heiji's preference) or a theatrical production (Kazuha's preference). They make a bet, with the person who successfully solves a particular murder case getting their way. Heiji takes the bet seriously at first, but after seeing Kazuha at the point of tears, changes to trying to give her hints instead. Unfortunately, he puts too much effort into it and solves the case himself.
  • Date A Live's 13th episode dedicates its first half to Shido attempting to botch his date with Origami in the worst way possible as a means to get her off his back. To wit: he asks her to dress up in a School Swimsuit with dog-eared headband, "kneel like a bitch" and accept him leading her with a leash. She does exactly that. When he breaks down in tears and apologising, she responds with "Woof~". In other words, it fails epically because Origami is THAT much of a devoted love interest with a disregard for public opinion and a blunt attitude, dumbfounding everyone in the process.
  • Doraemon has a humorous example of this. Noby/Nobita uses one of Doraemon's gadgets and meets a goat-like alien. Because using this particular gadget literally forces extra-terrestrials to come, a good reason as well as a crazy amount of hospitality is needed. We wouldn't want them getting any ideas. Realizing that they need to make their guest as comfortable as possible, they serve him all of the good food they've got, only to discover that the only thing he absolutely LOVES to eat are Noby's failed tests. He soon returns with friends who demand another one, which he gladly says he'll bring.... only he doesn't because by some unforeseen miracle he passed.
  • In Dr. STONE, Ginro was against joining the voyage to discover the cause of the mass petrification due to how dangerous it is. However, he also wants to impress all the girls, so he decides to fake a change of heart by attempting to swim for the ship after it's already too far away to reach, and claim that he totally would've joined the voyage if they hadn't left without him. Unfortunately for him, the ship's crew notices him and sends out a boat to drag him aboard anyway.
  • A variation of this can be found in Full Metal Panic!, where Sōsuke purposefully is very curt and detached from people so they won't be friends. It always fails, and he constantly ends up with a bunch of unwanted True Companions that all really like him.
  • In Fun Territory Defense By The Optimistic Lord, the first goal of Van Nei Fertio after getting a back-water village as a territory is to Do Well, But Not Perfect because if he does poorly, he will die, but if he's too prosperous too quickly, he will gain the attention of all the local powers, including his father who exiled him, and all will see him as a threat. Not only does he have to deal with a bandit attack as he arrives but when he's beaten the bandits, those that ran off come back being chased by a legion of beasts known as "armored dragons" and defeating said beasts in self-defense immediately draws the attention of all the local powers. It's only because his country's own king gets to him first, thanks to his neighbor's own Arranged Marriage ploy, that he's able to weather the storm.
  • A recurring plot element throughout Haven't You Heard? I'm Sakamoto is Acchan and other bullies trying to make Sakamoto slip up or look stupid. They do this out of jealousy for how easily Sakamoto attracts the attention of all the ladies. Whenever the bullies try, Sakamoto is Inexplicably Awesome, and always just ends up looking even more cool than he did before.
    • The bullies remove Sakamoto's desk from class so he has nowhere to sit. Sakamoto opens the window and sits on the windowsill instead, complete with Hot Wind.
    • When the bullies corner Sakamoto with a DVD he needs, they say he'll only get it if he rents a porn movie for them. But Sakamoto effortlessly manages to slip in to the 18+ section undetected, and has such a good poker face that he bluffs the store owner into letting him rent a dozen porn movies.
    • The bullies hold Sakamoto's balloon sculpture hostage at the culture festival, threatening to pop it if he comes closer. Sakamoto makes a gun out of balloons, and somehow uses the gun to pop the balloons himself, even making another sculpture out of it.
  • In an episode of Hyouka, Oreki attempts to convince Chitanda that he'd just gotten lucky with his theory-making (stating that theories can stick to anything) by playing a game with her. He follows an intercom announcement calling a student to the staff room for something happened at a shop the day prior to an explanation that's logical but likely too complicated to be correct. His theory was that the student had purchased merchandise at the shop with a counterfeit 10,000 yen bill that had been given to him as payment (this had been a problem that was talked about on the news recently), and then felt guilty and wrote an apology letter (which is why the announcement was read using the date instead of "yesterday"), leading police to turn up at the school (thus the announcement only being read once, as the school officials were nervous, and him being called to the staffroom instead of the chairman's office.
  • A recurring gag in Isekai Tensei, Ore ga Otome ge de Kyuuseishu: the male protagonist has been sent to the world of an otome game, that he hates. He hopes to finish the game without getting entangled in any romance with the male love interests; but to do so, he must keep his affection levels below the threshold where the romance route will kick in. So he takes part in game events intended to win over the characters, and sabotages them... but being a comedy, he often ends up raising their affection unexpectedly.
  • The premise behind Irresponsible Captain Tylor is that Tylor is so incredibly irresponsible that the United Planets Space Force puts him in charge of a Ragtag Bunch of Misfits onboard the worst ship they have in the fleet, and giving him assignments in every intent that he will fail and either be killed in the process or face any justified reason to discharge him from service. He ends up being so unintentionally successful, that he ends up bringing peace throughout the two warring factions, much to the annoyance of his superiors.
  • JoJo's Bizarre Adventure:
    • In Diamond is Unbreakable, Koichi catches the romantic attention of the beautiful but terrifying Yukako and wants to get out of it. Josuke and Okuyasu help him out by spreading rumors that Koichi is a real scumbag, in the hopes that it'll put off Yukako; instead, she abducts him and locks him in a house so she can "fix" him and turn him into a proper young man.
    • The Sugar Mountain arc of Steel Ball Run is like this, with deadlier consequences than usual. Due to the effects of an enemy Stand, Gyro and Johnny must rid themselves of everything they obtained in a recent Honest Axe trade. The problem is that their attempts to rid themselves of everything often wind up with them getting more: for instance, Gyro tries to buy up a bunch of worthless property, only to be accosted by a geologist asking about the copper ore in the nearby hills. After finally disposing of all their wealth, they then have to trade away a pair of mummified ears... the one item they were after in the first place.
  • In one chapter of Kaguya-sama: Love Is War, Kashiwagi's boyfriend comes to Maki for advice on an anniversary present. Maki, hoping to make the two of them break up so she can have him for herself, suggests that he get her a tacky heart necklace. Kashiwagi ends up loving the gift so much that they end up getting to first base in the middle of the hallway.
  • In a K-On! episode, Tsumugi decides she wants to get hit on the head, but Ritsu doesn't want to do it without a reason, resulting in various attempts that fail miserably.
  • A grimly hilarious example occurs in the 4th Ninja World War arc of Naruto, when Kabuto resurrects a number of famous and extremely powerful ninja. He then controls their bodies and forces them to fight their former allies, though they can usually still talk of their own free will. Some prove to be so tough that even when they outright explain what they're about to be forced to do, it doesn't help. The trope is indisputably played best with the Second Mizukage, whose desperate attempts at getting defeated are all thwarted because his illusions are so complicated, even an entire army can't understand his explanation of them.
    Second Mizukage: I keep trying to tell you, attacking me now is useless! I'm nothing but a mirage! Attack the clam first! I told you, the clam's creating the mirage! Oh, COME ON! I've told you! I've told you already! That clam is a mirage too, you idiots! Aim for the real one, GODDAMMIT!!!
  • An early episode of Pokémon: The Series has a trainer who needs a Paras to win battles in order to evolve into a Parasect in order to make an experimental medicine. Since it's for a good cause, Ash tries to deliberately let the Paras win. Unfortunately, his opponent is so pathetic that it loses even as Pikachu and Squirtle hold back, and his third choice, Charmeleon, makes his disobedience known.
  • In one episode of Power Stone, a number of characters have been sent to work as slave labour in the mines to pay off their gambling debts. Falcon and Gunrock come up with a plan to rescue them by losing everything and being sent as well. Cut to them holding massive piles of cash.
  • Played for (what else?) laughs in Ranma ½. Ryōga receives a magical drawing on his belly which gives him superhuman fighting abilities. But the drawing is so ridiculous that he wants to get rid of it (it also compromises his Secret Identity since it also appears on his cursed form), and the only way to do that is to lose a fight. Ranma, of course, agrees to help. Unfortunately, Ryōga's fighting abilities have become so superhuman that even when he's blindfolded, restrained, and weighed down, and later in his little black pig form, Ranma can't lay a finger on him.
  • Rebuild World: When Akira gets a request direct from the Hunter's Office to assist in the extermination of the Yarata Socrpion nests, he tries to get them to drop him from the mission by adding on a series of ridiculous demands like having the government pay for all the ammo he uses, getting additional pay for every scorpion he kills, and being allowed to move freely on his own. To his alarm and chagrin, they agree to all of his demands, forcing him to go on the mission.
  • In The Saga of Tanya the Evil, Tanya writes the recruitment notice for her rapid-response flight mage wing with plenty of emphasis on both extreme danger and low pay of the job in the hopes of dissuading recruits, which will make the brass give up on the idea and give her a nice safe desk job away from the front lines instead. Unfortunately, the Empire's populace is firmly convinced that War Is Glorious, and the notice comes off as Dare to Be Badass instead. Afterwards, she puts the recruits through an absolutely horrific Training from Hell, hoping that they all wash out. Every recruit passes the training, and they are so capable that she and the newly formed wing are sent out constantly into the most dangerous situations since the brass are (rightly) convinced they are up to the challenge.
  • In Trigun, Vash at one point gets entered into a sharpshooting contest. Not wanting everyone to know that Vash the Stampede is participating, he decides he'll Do Well, But Not Perfect and gets wasted the night before, but since he has to put effort into not hitting targets, Vash wound up so hungover he couldn't fail and won anyway.
    Vash the Stampede: Oops. Oh no. I hit them all.
  • In Trapped in a Dating Sim: The World of Otome Games is Tough for Mobs, the protagonist Leon reincarnates as a nameless NPC in an Otome Game, and wants to live a normal life in peace and quiet. Unfortunately, his attempts to get demoted by doing bad behavior, and to shift fame and glory onto the game's five capture targets instead of himself, all end up backfiring, leading to him being promoted. The former, due to having one of the most powerful aristocrats in the Kingdom backing him, and the latter because of said capture targets' Honor Before Reason stubbornness and the appreciation of their families for the bribes Leon sends them.
  • In Tytania, a weak planet sends a starfleet against the almighty Tytania empire just to not surrender without a fight and do it on more or less profitable terms. They assign the worst officer they have as the admiral, but he somehow manages to win the battle. Hilarity Ensues. Well, it doesn't turn out to be fun, eventually.
  • Urusei Yatsura: When he learns that Ten is writing Sakura a love letter, Ataru instead ghostwrites one for him, filling it with all sorts of over the top lechery to dissuade Sakura from meeting up with him. She shows. Zigzagged, as she really showed up to beat the shit out of the pervert who dared to write the letter.
  • Welcome to Demon School! Iruma-kun: In the opening arcs, Iruma is constantly trying to keep a low profile as he is a human in a world full of demons that would eat him if they learned what he was. However, (partially due to his adoptive grandfather's influence), he repeatedly ends up in the spotlight, usually accidentally accomplishing some sort of amazing feat that only makes his fame grow. Eventually, he becomes more self confident and essentially gives up trying to hide his presence and focuses more on improving himself (though he still continues to (mostly) successfully hide what he is).

    Board Games 
  • Checkers has a rule that you must capture an opponent's piece if you're able to. As such, it can be played with a variant rule where the goal is to lose all your pieces as soon as possible. Since both players will be trying to do so, one of them will invoke this trope.
  • In 1979, Parker Brothers produced "The MAD Game", a reverse-Monopoly game where each player starts with $10,000, and you win by losing all of your money. If by some bizarre coincidence your full name is "Alfred E. Neuman" (MAD's mascot), you may end up acquiring a unique bill worth a very specific amount of money... which you can never get rid of, so you inevitably lose. Except there's numerous opportunities to force another player to trade places with you. It's too bad you'll never actually use the bill unless you bend the rules.note 
  • In 1965, Avalon Hill created a game called $quander (Squander), in which each player started with a million Squanderbucks. The first player to lose all of his money won the game. After some changes, it came to the US as well as other countries under the title Go for Broke!
  • In Suicide Chess, you must capture an opponent's piece if able and you win the game by losing all your pieces.

    Comic Books 
  • This has happened in Archie Comics a few times:
    • One Josie and the Pussycats story had their sponsor Mr. Cabot lamenting the Pussycats' success, having sponsored them because he thought they'd lose money and he'd get a big tax loss. He tries to sabotage both the Pussycats themselves and the seniors' club he owns by having the Pussycats play there, expecting them both to lose money and give him a big tax loss. Unfortunately, the Pussycats are a hit, and Mr. Cabot's club gets a six-month waiting list for people to join, earning Mr. Cabot another huge fortune.
    • In another story, Jughead tried to prove that people would believe anything. To prove it, he makes up a pamphlet with bogus stock tips and puts it with Mr. Lodge's morning mail, expecting Mr. Lodge to follow the tips, lose a fortune and prove his point. The first tips earn Mr. Lodge $60,000 and get him out of another company right before it crashes, which Jughead dismisses as a fluke. Following through on the rest of the tips earns Mr. Lodge a grand total of over $2 million.
    • In yet another story, Reggie lost a game of tennis to Archie and started complaining, and Veronica called him out as a sore loser. So, he decides to purposely lose a game against Archie, and act graciously. But he just can't seem to lose a game afterwards, no matter how badly he plays. Eventually, he breaks out in a fit over winning at another game of tennis.
  • This is the Running Gag for the Asterix story, "Asterix and the Laurel Wreath": to try and get into Caesar's palace to steal his laurel wreath (it's a long story), they get the bright idea of selling themselves as slaves from a vendor called the House of Typhus. Finding out they actually got bought by a common Roman patriarch and not Caesar, they try to get themselves thrown out; first by serving up a deliberately grotesque dinner (the family's son demands they be kept, because it works as a Hideous Hangover Cure), and then by waking them all up in the middle of the night by banging pots and pans and claiming it's a Gaulish tradition to throw celebrations like this (the inspired family promptly throws their own raucous all-night party, which keeps the Gauls up all night).
  • A hilarious example occurs in the "Harley and Ivy" arc of Batman: Gotham Adventures. Gal pals Harley Quinn and Poison Ivy hear about an upcoming stupid action movie themed around... well, them. Naturally pissed off, they head to Hollywood to stop it, but Ivy sees how much money the flick is budgeted for and decides to take over. The two don't plan to release it — Poison Ivy's just in it for the money and Harley likes seeing the Batman actor blow up "over and over and over again" — but after they're sent back to Arkham, the film's backers release it anyway. It quickly becomes a smash hit. (Harley even wins an Oscar, attending the ceremony with a police escort.) Of course, the only reason the movie was released was because the company had no choice due to all the money Harley and Ivy sunk into it, and the reason it was a hit was because people thought it was supposed to be a parody of overblown action movies and considered it epic.
  • Bone has Phoney's Mystery Cow scam for the Great Cow Race; He spreads rumors that Gran'ma Ben (The usual winner) is getting too old, while hyping the Mystery Cow (Smiley in a cow suit) as the sure winner. With everyone betting on the Mystery Cow, all Smiley has to do is throw the race, allowing Phoney to keep the pool for himself. It flops tremendously when Lucius bets his pub on Gran'ma, forcing the Bones to try and win. They fail, of course, and end up seriously in debt to Lucius and Gran'ma.
  • In the Vertigo limited series Cruel and Unusual, disgraced TV producer Bobbie Flint has been put in charge of the sleazy network owner's privatized jail, and is appalled by the inhumane conditions; prisoners are stored in silos, guards constantly beat prisoners and no one cares, and the owner won't spring for a new electric chair despite the old one setting two out of three prisoners on fire. She comes up with an idea; host the nation's first televised execution (of an obviously insane prisoner) to let the public see how bad it is and start the outrage machine. Unfortunately, it has the opposite effect... and Jail TV is born.
  • Disney Comics:
    • A Donald Duck story pretty much retold The Producers: A father-and-son duo of shady film makers plan to make their big, expensive movie Laura of Arabia fail spectacularly and run off with the investor money. (If the movie doesn't fail, the duo will owe the investors 753% of the movie earnings.) In order to ensure a flop, they sabotage every part of the filming process that they can. This includes hiring a completely inexperienced woman for the title role, not buying vital equipment, and employing Donald (who they believe is a huge, incompetent idiot) to do whatever needs to get done, so that he'll mess things up. Unfortunately for the film makers, Donald turns out to be excellent at all his duties... Except for when they make him a cameraman. When it's time to film the big, epic battle sequence, Donald's job is to film it from above, from the top of a pyramid. But he's exhausted from all his hard work, and sleeps through the entire shooting. And this was his only chance—the scene can't be re-shot. Then he's supposed to cut the scene, but decides that it doesn't work without the perspective from above. But one of the film makers arbitrarily re-cuts the scene while Donald is asleep, as a safeguard in case Donald turns out to be a decent editor. By pure chance, the arbitrary re-cut works excellently, and the scene ends up getting praised by critics, making the movie a huge success.
    • A Mickey Mouse story had the main investor of a stage director who had produced nothing but flops thus far go this route by having the play insured. Unfortunately, the director's latest ridiculous project (an adaptation of Hamlet set in the world of soccer) seemed to be actually working, leading the investor to dress up as the ghost of Shakespeare to try to sabotage the production.
    • In the short Carl Barks comic "The Colossalest Surprise Quiz Show", Uncle Scrooge takes part in the title quiz show. The show gives big sums of prize money to the contestants and the questions are ridiculously easy. However, Scrooge learns that he's reached the upper limit of his income tax bracket. This means that he would actually suffer a huge loss if he landed any money from the show. He doesn't want to chicken out, so he goes to the studio, but answers every question: "I don't know." The result? He receives a special bonus prize of $120,000 for being the dumbest person in the history of television.
    • A William Van Horn story had Donald taking a high tech aptitude test after being fired for the Nth time and being told that he's best suited for doing the lowest possible jobs. Whenenver he gets one of these jobs, a disaster occurs which he then solves, prompting his superiors to promote him... and is forced to resign, to stay as low as possible. The story ends with his nephews congratulating him on being promoted several times despite the test stating that he would always remain in the bottom of the ladder... with Donald (looking like he's about to burst into tears) saying "Yes... but I couldn't even succeed in THAT!"
    • The billionaire's club in Duckburg holds a contest awarding chess sets made of diamond, gold, or silver to the three most successful businessmen of the year, and a worthless wooden pawn to the worst one. For some reason Scrooge actually wants the consolation prize, and gets Donald to replace him as head of his business empire in the hopes that he'll ruin his profits for the year while Scrooge goes off on a holiday. Near the deadline he is livid to find out that Donald has actually been acting responsibly and his profits have shot through the roof. Then it's subverted when a stock market crash in the last minute makes Scrooge the biggest loser in the contest in one swoop. Oh, and the reason why he wanted the wooden piece was because it would have completed an invaluable chess set that Scrooge already owned and kept hidden in a vault.
      • Before getting Donald to replace him, Scrooge tried to sink his profits himself through foolhardy acquisitions... Except his reputation got the "lesser" billionaires to wonder what he was doing, find ways to turn them profitable, and investing in them, to Scrooge's growing horror. That was when Donald showed up to ask him for some money, and Scrooge instead gave him the post hoping he'd pull it off.
    • The Carl Barks story entitled "Spending Money" tells of Scrooge having too much money to the point that every bank in town will not take another dime of his money. So he enlists Donald and the nephews to go on a spending spree with him. They spend money on a car with ermine seat covers only to replace car after car when something is wrong with the previous one, feeding a giant troop of Junior Woodchucks, staying in expensive hotels, and buying tourist souvenirs at super high markups. In the end, the ducks end up spending none of it as Scrooge proves that he is the economy.
  • The first arc of Ex Machina concerns an extremely offensive piece of art. It turns out the artist was so sick of the art world that she sought to make something that no one could possibly praise. She fails, it appears in the Brooklyn Museum of Art, and she vandalizes it in disguise so it can be taken down without her publicly giving in to pressure to remove it.
  • One issue of Marvel Adventures Spider-Man sees Peter get roped into trying out for the baseball team, and he discovers that he's a natural outfielder, much to his shock. Turns out all the years of fighting bad guys as Spider-Man have honed his muscle memory to the point where he can't not move fast and catch projectiles.
  • In the Mortadelo y Filemón book ''El Tirano", the titular pair of agents are given the mission to eliminate a fascist dictator (a parody of Augusto Pinochet), but their constant failures actually stop murder attempts from other people (not to mention screwing with each other's attempts). When they are told they have to protect the man so that he is taken to Spain and judged for his crimes, they try, but their attempts at protecting him subsequently send him to the intensive care wing at the closest hospital.
  • Nightwing: When Nightwing is falsely implicated in the death of Blockbuster (who was really killed by Tarantula), the recently promoted Captain Rohrbach (his Friend on the Force) hides a witness statement and assigns the case to Detective Patitz, a Shrinking Violet recent transfer from Robbery Division who has never investigated a homicide. However, Patitz is a skilled investigator who quickly builds a case against Nightwing after all.
  • In Rising Stars, Randy Fisk, an ex-super hero, gives up his cape and runs for president. But fails several times in a row. In one season, he is losing so badly in the polls that he just gives up and decides to just spend the rest of his campaign wearing his costume and catching criminals. By coincidence, the two other candidates have sabotaged themselves and the voters get to choose between two criminals and one super hero. ...He wins.
  • An issue of the Silver Age World's Finest has Batman suddenly receiving a bag filled with a million dollars, and desperately trying to spend it all on worthless investments to help someone stuck in a rip-off of Brewster's Millions. Unfortunately, Robin and Superman (who aren't privy to the deal) think Bruce is in financial trouble, and sabotage every scheme. (For example, when Batman buys an empty gold mine, Superman throws down a meteor filled with silver, leaving Batman with even more money.)

    Comic Strips 
  • A Beetle Bailey comic had General Halftrack getting angry about a new television comedy show about an idiot general that looks a lot like him. He happens to run into the screenwriter getting drunk at a bar, who explains that he used to do cultural shows and was ordered to make a comedy. He then created what he saw as a terrible show in an attempt to get fired, but the show took off and he's now stuck writing it. He and Halftrack then hatch a plan to get the show off the air by writing an episode consisting solely of soldiers marching. The audience hates it... but the critics praise it as an avant-garde masterpiece.
  • One Blondie (1930) comic strip featured a wealthy person coming to the company playing a game of golf with Dagwood and Mr. Dithers. Mr. Dithers tells Dagwood to do poorly in the game so the newcomer will look good. Dagwood accidentally plays a great game.
  • The Bumpkin Billionaires was a long-running UK comic strip clearly inspired by The Beverly Hillbillies, and entirely based around this trope. The title family won a huge sum of money, and quickly discovered that they hated being rich... and so each strip would detail a new scheme of theirs designed to lose as much money as possible, much to the despair of their bank manager. Of course, their schemes were destined to fail, often resulting in the family ending up even richer.
  • Dilbert:
    • Professional Slacker Wally wants to get fired, because that way he can get a generous severance package. Thus, he acts as incompetently as possible so that management will give him the axe. The problem is that the company is manned by the trope-naming Pointy-Haired Boss, so everything Wally does gets the PHB's approval, is completely ignored, or causes someone else to be fired in Wally's place. All the while, Wally keeps slacking off and not doing his job, yet is consistently frustrated that he can't seem to get fired for it. This is based on someone Dilbert creator Scott Adams worked with, who was in a similar situation where a coworker realized that the severance package for getting fired was so generous that it outpaced his salary. Adams said of this coworker that "this wouldn't have been much fun to watch, but [this coworker] was one of the most brilliant people I've met, and completely committed to his goal" of acting awful. In the later Dilbert treasury What Would Wally Do?, Adams briefly mentions in his intro that said colleague did ultimately succeed in losing his job.
    • Also, the following exchange:
      Dilbert: The company pays me ten dollars for every bug I fix in my code, Ratbert. I want you to do your little rat dance on my keyboard so I'll have lots of bugs to fix.
      Ratbert: (dancing around) How am I doing?
      Dilbert: Not so good. You just authored a web browser.
  • Discussed by Garfield and Jon in the November 27, 2015 strip.
    Jon: What would happen... if I tried to be a failure... and failed?
    Garfield: We'd be rich!
  • An arc of Tank McNamara had sports fanatic Sweatsox coaching a Little League team, and learning that to advance to the playoffs, his team had to lose the current game. So, tied in the bottom of the ninth, he sent the most out-of-shape boy to bat. Sweatsox, with a smirk, thought, "I've forfeited." The boy, however, managed to get his first hit of the year, winning the game, and was carried off on the shoulders of his cheering team; Sweatsox was furious — and his wife said sarcastically, "That's the trouble with kids these days. They got no sense of values." (Sweatsox did at least have the grace to look ashamed of himself when she said that.)

    Fan Works 

Crossovers

  • Big Human on Campus: Kouma desperately tries to avoid getting paired with Ranma in their Fight Club. Unfortunately for him, this all comes to naught when Riza hears him muttering "Not Saotome, not Saotome" under his breath and immediately puts them together.
  • In Enter the Dragon, Professor Quirrel opts to attempt an extremely dangerous, volatile recipe in hopes that it will blow up in his face and "accidentally" kill him, as he considers that preferable to having to complete his master's orders. Unfortunately, he can't make himself intentionally fail, and the potion turns out successful.
  • Family Bonding And Other Perilous Pursuits: Danny's whole class actively tries to avoid winning the Thomas & Martha Wayne Foundation, as none of them actually want to go to Gotham. They win anyway, leaving Danny utterly baffled.
  • Hero Academia D×D: Hatsume has no intention of winning the Sports Festival; she just wants to use it to show off her babies, then step out once she's done. When Katsuki launches himself at her, she hits him with a capture net, causing him to fly out of the ring.
  • In Neither a Bird nor a Plane, it's Deku!, Izuku gets into a spat with Kendo Rappa over a Beebo plush and meekly tries to back out. Unfortunately, they're both egged on into playing the "Test Your Strength" Game for the doll. Izuku tries his hardest to just lose and get it over with, but his lovetaps alone are stronger than Rappa's casual punches. After being pushed to go all-out, Izuku utterly wrecks the machine, prompting Rappa to challenge him to arm wrestle instead. At this point, Izuku is fed up with him and crushes Rappa so badly that Rappa's arm flips around 180 degrees.
  • In The Pokémon Squad episode "Fifty Shames of Gray", RM and Brock write a Troll Fic based on The Fairly OddParents!. However, the fic becomes so much of a smash success that it ends up getting a movie deal!
  • In the second Love Hina arc of Sleeping with the Girls, the main character walks several of the local girls through how in worlds that run on the Rule of Funny, such as theirs (a romantic comedy universe), plans will almost always fail because it's funnier that way, even if you are planning to fail. If you are planning to fail, you will almost inevitably succeed.
  • In XSGCOM, while negotiating with the goa'uld System Lords, Weir wants to avoid going to war with Ba'al, so she tries to make a request that they will refuse by demanding that the goa'uld cede them every star system within two and hundred and fifty light-years of Earth. They go for it, and Earth inadvertently becomes an interstellar empire.

Batman

  • Bruce Has a Problem: In an effort to ensure that Sharpe or Garcetti don't become the next Mayor of Gotham, Two-Face decides to run himself. On top of his criminal background, he's confident that calling for Gotham to secede from the United States is far too insane of a platform to attract too much attention. However, many of Gotham's residents remember how the US Government turned its back upon them during the events of No Man's Land, so his calls for secession prove more popular than he'd anticipated, much to his surprise.
  • Error In Judgement: Bruce Wayne attempts to run for mayor of gotham city as part of his camoflage as an incompetent wealthy hedonist.

Bleach

  • One subplot in Red Duty, Black Honor is that the Kuchiki elders require either Rukia or Byakuya to get married. Rukia suggests to them that she marry Ichigo, figuring all of them would hate him as a candidate and would fight amongst themselves, delaying their decision. Instead...
    Rukia: I didn't think they'd agree to it!

Danganronpa]]

  • The Ultimate Hope chronicles a version of events where the murder game results in the trapped students befriending each other and becoming better people... much to the frustration of Junko, who'd been trying to force them to kill each other.

Daria

  • God Save the Esteem: One of the "Meanwhile, Sideways in Time" segments follows Dire Daria as she attempts to get fired from the Okay to Cry Corral. Her efforts wind up making her the most popular counselor there.

Fullmetal Alchemist

  • build your wings on the way down: Concerned that Edward is far too arrogant about his abilities for his own good, Roy attempts to give him A Lesson in Defeat by permitting him to try and save Nina after she's turned into a chimera. To his utter shock, Ed succeeds — meaning that now Roy has to scramble to keep their corrupt superiors from finding out and exploiting his skills.

Harry Potter

  • Harry's New Home: Snape wants to be seen as a Sadist Teacher who regularly reduces his students to tears. To his dismay, his occasional moments of kindness towards Harry cause him to be increasingly regarded as a Cool Teacher instead.
  • Harry Potter and the Methods of Rationality reveals that Lord Voldemort is this trope. Tom Riddle created the "Lord Voldemort" persona as an absurd Card Carrying Politically Incorrect Villain to work out the method for playing a villain and get the stupid mistakes out of the way for his next grand role to be defeated by his "David Monroe" persona and propel "Monroe" to hero status. Sadly the Ministry was so utterly incompetent that they couldn't actually defeat Voldemort, so he unleashed "Monroe" on him... which was hampered by the ministry doing a decent job of keeping Monroe from accomplishing anything to help them. He eventually gave up and just became an Evil Overlord because it was more fun.

Hellaverse

  • In Wings, Lucifer's plan hinges on making sure the Altar Diplomacy he set up between hell and heaven fails by deliberately chaining Octavia into it, hence making her likely to hate her future husband before the marriage even started, and forcing concesssions from heaven. However, he neglected to think of the possibility that Octavia and her husband could end up loving each other anyways.

Miraculous Ladybug

  • One step backwards and Three forwards: Felix makes skirting along the line of flagrant disobedience into an art form, defying and challenging his father at every turn while making his feelings about Gabriel's decisions very clear. To his horror, Gabriel actually seems impressed by his son's willfulness, showing more pride in him than he ever did in Adrien. Which is a problem, since Felix is Adrien — or at least, the part of him that remembers the original reality.

My Hero Academia

  • In Beezuku, Katsuki is secretly terrified of bees, so he's less than thrilled by Izuku's Adaptational Superpower Change. He repeatedly attempts to flunk out of U.A. so that he won't have to be around Izuku all the time, only to repeatedly impress their teachers as they mistake his conduct for truly heroic behavior.
  • DeusVerve's Springtime for Todoroki revolves around the notion that Shouto wants to get expelled from U.A. so that he can pursue his dreams of becoming a professional snowboarder, recontextualizing many of his canonical actions as attempts to get himself kicked out of school... which repeatedly fail. Much to his utter bafflement.
  • The whole point (initially) of Not That Kinda Fired: Izuku works for Endeavour as an analyst, but he's fed up because, among other things, some people from Accounting keep dropping their work on him. However, he can't quit because the contract he signed would land him in economic trouble - but, after seeing Endeavour's Number Two Burnin' firing an intern for flirting with her at work, he realizes he could instead try to get fired. However, everything he tries ends up making him more appreciated by Endeavour and makes it harder to get himself fired (never mind the fact that, outside of this, he does an excellent work and uncovered a villainous plot to create knock-off Nomu out of Rei Todoroki's blood).
    • When he has to make coffee for Endeavour, he decides to add mayo to it. Endeavour loves it so much he makes Izuku his personal coffee-maker and gives him a raise.
    • Since Endeavour hates music playing during office hours, Izuku rigs his MP3 player to the agency's PA so it will start playing music the next morning. Endeavour dislikes it... but when he sees the mood and productivity have improved, he approves of it.
    • When Shoto (who, due to not having Izuku as a friend, still refuses to use his fire side) comes to the agency, Izuku decides to get into a fight with him. He gets so involved and passionate about it that he convinces Shoto to learn how to use his fire side.
    • He then attempts to try the same thing that inspired his idea, flirting with Burnin'. He asks Mineta for some of the pick-up lines he used as a Hormone-Addled Teenager and waits until after office hours so he can use them on Burnin' and escape on his bike if she gets angry. Since he's visibly nervous and reading the lines out of cue cards (and visibly rejecting the worst ones), Burnin' finds him Endearingly Dorky and accepts to go out on a date with him.
    • For the office costume party, he decides to go out as All Might, complete with padded costume, stilts, wig - and his impression of All Might instead of a mask. Endeavor becomes impressed at how good the costume is.

My Little Pony: Friendship Is Magic

  • In Roll for Initiative, Rainbow Dash is playing a game of Dungeons & Dragons with the rest of the Mane Six. Due to a combination of reckless playing and unlucky dice rolls, Rainbow's characters get killed in rapid succession. At the next session, Dash embraces her bad luck and creates a new character: Trixie, who she wants to die — at which point the Random Number God suddenly swings in Trixie's favor. No matter how suicidally reckless Trixie acts, she somehow walks away unscathed from every fight. It culminates with Trixie single-handedly killing a Tarrusque, then eating its life force...
    Twilight: Rainbow, I have good news and bad news for you. The good news is that Trixie is gone forever. You can never play as her again. [...] As for the bad news, you just turned her into a goddess.

Naruto

  • First Try Series: In First Try: Team 7, Naruto doesn't want to be saddled with Sasuke and Sakura as teammates, so he tries to fail the bell test. Despite his best efforts, Kakashi rewards him with a bento; when Naruto then gives the bento to Sakura because he's not interested, Kakashi treats that as though he passed his Secret Test of Character and passes the whole team, to Naruto's dismay.
  • Five Petals: Played for Drama during the climax of the first story in the series: Danzo attempts to use Sakura as an Unwitting Pawn, convincing them that he wants them to become a Fake Defector and serve as his mole inside Sound. In reality, he's banking on Sasuke attempting to stop their "defection" so that his agents can attack and steal Sasuke's eyes. He's utterly furious when things don't go as planned, fuming as he recieves his first bit of intel from his unwanted mole.
  • The Uzumaki Tales: Return Of The Whirlpool: Shikamaru believed that forfeiting his match against Temari would make a bad impression upon the judges, since he'd practically won before giving up. Instead, the judges were impressed by the reasoning he gave in the ring, deciding to promote him to chuunin.

RWBY

  • Knight of Salem: When Salem orders Torchwick to enter Jaune into the Vytal Tournament, he decides to deliberately make Jaune's entry information be as obviously fake as possible so that Ozpin and his followers will immediately see through it. While Ozpin's ilk do immediately recognize the forged entry for what it is, they decide that playing along with Salem is actually their safest option, so they accept Jaune in.
  • In Linked in Life and Love, Torchwick decides to help Cinder's faction out because he believes Ozpin is The Omniscient, figuring that he can slip away with his profits while they're arresting Cinder. Turns out that Ozpin is Not So Omniscient After All, having no idea about Cinder's scheme, meaning it goes much further than Torchwick ever anticipated.
  • White Sheep:
    • Qrow, believing that Jaune is the half-brother of Qrow's niece Yang, decides to sabotage Jaune and Yang's burgeoning relationship, despite muttering that this will make him "the biggest asshole." He tells Jaune that Yang (a shameless Tomboy who spends most of her free time punching things) secretly loves formal courtship. So Jaune, rather than taking Yang to an arcade or something like Yang expected, instead calls his Uncle Watts, who gets them the most expensive reservation at the most expensive restaurant in the city. It's the kind of place people go on their fiftieth anniversaries. Yang ends up enjoying being treated like a princess for once, and while Watts went way too far, the mutual embarrassment also brings her and Jaune closer together.
    • The match between Teams CMEN and WJRP has this on both sides. CMEN don't want to win as that would require them to show their real skills. Meanwhile, Jaune of WJRP wants CMEN to win so that Cinder (its leader) will be chosen to become the Fall Maiden (though his teammates don't know about this and fight seriously). Complicating things further, Mercury of CMEN is briefly convinced to fight seriously thanks to his girlfriend's encouragement, thus showing off his real skills. In the end, the match ends with neither team's victory due to Cinder having to rescue a drowning Jaune.
    • Weiss' father Jacques sends her to negotiate with Ironwood to end the trade embargo with Vale, expecting her to fail so he can disown her and make Whitley his heir. Instead, she actually succeeds by both understanding Ironwood's motivations (keeping the White Fang from stealing more Dust) and coming up with an acceptable workaround, rather than just complaining about the lost profits and demanding he drop the embargo like Jacques would.

The Saga of Tanya the Evil

  • Pretty much the whole point of A Young Woman's Political Record. Tanya von Degurechaff tends to fail upwards, fail at failing or her actions have unexpected consequences that work entirely to her benefit. So far:
    • She joins a minor political party for a cushy job as a party functionary. She winds up as Chancellor.
    • Tanya provokes the Francois Republic with an eye towards being removed from power in exchange for a comfortable exile. The other Great Powers backstab the Francois Republic and basically tore up most of the Treaty of Triano. Notably this was a major plank in Tanya's (thought to be impossible to achieve) party platform.
    • Tanya seeks to get voted out of office peacefully before the problems of post-War Germania can rear their ugly head. She starts a government enterprise to splinter her own ruling coalition (which contain radical Free Market Capitalists). She puts a man to work designing a cheap car for the masses thinking it would be a marginal profit. Instead he creates the Volkswagen Beetle, one of the most successful cars of all time.

Sailor Moon

  • In this fanart, Sailor Mercury fills a cookie jar with spicy chili cookies in attempt to make Chibi-Chibi afraid of them (so she would stop stealing them). Chibi-Chibi ends up enjoying them more, intentionally inducing a Fire-Breathing Diner like a dragon.

Star Wars

  • Roger, Roger: Palpatine engineered the Separatist attack on Kamino with the idea that it would do only minor damage to Kamino’s cloning facilities, and would galvanize the Republic into putting more resources into the war effort. However, Ventress puts 711 in charge of the attack force, and the attack does major damage to the cloning facilities, with the Republic forces only barely averting their total destruction.

Trails Series

  • Isekaid To AJRPG As A Harem Member: After being assigned to Class VII, Jessica states that she doesn't have the skills necessary, and whoever placed her there made a mistake. Aurelia reveals that she was the one who'd assigned her there, whipping out her blade and threatening her with it. When Jessica calmly stands her ground, she unintentionally passes Aurelia's Secret Test of Character, leaving her confident that she'd made the right choice in her initial assessment.

Warhammer 40,000

  • The Crack Fic Ciaphas Cain, Warmaster of Chaos is all about this; after Cain accidentally becomes the leader of a Chaos-rebellion against the Imperium, he routinely tries to sabotage his new planet from within so that the inevitable Imperial retribution goes as smoothly as possible. Unfortunately for him, all his ideas of "sabotage" are Imperial ideas of what's foolish, things like giving workers time-off and safety standards, and allowing Tech-priests to actually invent new technologies; others, like trying to run his soldiers into the ground with ridiculously over-the-top training fails because they have Khorne's blessings, so the training only makes them stronger. Combined with the fact that he keeps the actual Chaos-worship on the planet restrained, Slawkenburg not only survives the Imperium (and the Orks and Drukhari) but thrives as a burgeoning utopia, while Cain is regarded as one of the greatest threats to the God-Emperor's realm. He's utterly miserable the whole way through, of course.
  • In The Guy Who Cried Grendel, the titular Non-Action Guy made a desperate charge against an Charnel Daemon, hoping to distract it and buy time for his teammates to escape while the daemon was busy brutally murdering him. And then he rolled a Critical Success for his knife strike and decapitated the daemon in one hit.

    Films — Animation 
  • A Bug's Life: The queen of the ant colony lets Flik go to find help with his crazy idea to fight the grasshoppers. This was only supposed to keep him out of the way, since his crazy ideas were becoming dangerous. Instead, Flik finds a group of circus performers (whom he mistakes for bug warriors), and brings them back to the ant colony, so the ant royalty now have to go along with a plan they clearly don't want to do. This, along with the grasshoppers realizing what the ants are up to, results in a "Fawlty Towers" Plot where the lie has to be kept going, gets exposed, and then maintained to fool the other group anyways.
  • The Little Mermaid (1989) has Ursula engineer a rather crafty gambit: She knows that the only thing Eric remembers about Ariel is her beautiful voice, so she makes her voice the price for the human-turning spell, reasoning that Eric will not recognize her or fall in love with her in three days. This backfires: Eric sees this poor, mute girl who looks like she washed up from a shipwreck and shows her hospitality. Her energy and excitable demeanor snaps him out of a mournful funk (ironically, over not being able to find Ariel) and he begins to fall for Ariel quickly. Ursula ends up needing to intervene herself and brainwash Eric in order to ensure Ariel doesn't fulfill her end of the deal.
  • This kicks off the plot of Mickey, Donald, Goofy: The Three Musketeers. Pete, upon being ordered by Minnie to find Musketeer bodyguards to protect her, deliberately picks Mickey, Donald, and Goofy, whom he considers to be completely unfit, and therefore making all the easier for him to kidnap her. It comes to backfire on him spectacularly when the trio actually starts becoming competent at their job.
  • In Spider-Man: Into the Spider-Verse, Miles purposely gets all the answers wrong on a quiz in an attempt to flunk out of Visions Academy, the private school he got enrolled in. His teacher, unimpressed, points out that getting a zero on a true or false quiz is astronomically unlikely, unless you actually know all the answers. She gives him a perfect grade.note 

    Literature 

By Author:

  • P. G. Wodehouse:
    • Peril at the Tee involves two crappy golfers playing a round with each other. As the consequences of winning would be to neither's liking, both of them attempt to throw the game. However, the methods they employ actually improve their technique. As an example, one of them is wearing a tight-fitting jacket, figuring it will restrict his swing into total ineffectiveness. Instead, it ends up correcting his chronic overswing.
    • In another P.G. Wodehouse story, an honourable young man comes to believe there is insanity in his family. He must therefore end his engagement (since he cannot condemn the woman he loves to marriage with someone who may go mad), but cannot say why in order to protect his family. He decides to behave outrageously so that his fiancee will break off the engagement herself or her family forbid it. Everything he does to this end causes him to be admired all the more for manly frankness. It being Wodehouse, the fact that this potentially tragic scenario ends happily for everyone is possibly the most pointless concealment of a spoiler in the history of TV Tropes.

By Title:

  • Canadian political satire The Best Laid Plans by Terry Fallis follows Daniel Addison, a Liberal Party political strategist who wants to leave politics and start teaching at his alma mater. Daniel attempts to destroy his credibility by convincing Angus McLintock, his new colleague/landlord, to run for Parliament for the Liberals even though he is considered unelectable (and doesn't actually want to be elected, and is only running in order to get out of teaching an English course to first-year engineering students, his most hated class) in the strong Conservative riding where they live. (Exacerbating the hopelessness of the Liberal cause is that the incumbent Conservative MP is also the nationally popular Minister of Finance.) Even though Angus refuses to participate in the campaign, or indeed to let Daniel do much, he wins by a narrow margin after the incumbent gets caught doing something very stupid three days before the election, rendering him unelectable in the riding. Upon learning he was elected, Angus admits he never wanted or planned to become an MP. When he rolls with his election, he follows his head and rejects "politics as usual", and becomes popular with the voters.
    • The sequel, The High Road, averts this trope by having Angus actively run for re-election, and win a close contest.
  • A variation in the Olivia Goldsmith novel The Bestseller. Gerald Ochs Davis Jr. is the son of a powerful publisher who part-owns Davis & Dash Publishing. He has dreams of being a great writer but can't quite make it. So he regularly cooks the records to take the sales of other novels and attribute them to his own books so they appear to sell better. For his latest, he decides on A Week in Firenze, reasoning that no one will miss any numbers from a novel about a bunch of old ladies vacationing in Italy written by a first-time author. Gerald is as shocked as everyone when Firenze is soon topping the bestsellers lists. It doesn't take long for the auditors to realize something is off about Davis & Dash claiming the biggest hit of the season isn't selling more than 30,000 copies and Gerald's scam is exposed with his own father firing him.
  • The Black Dahlia: A zigzagged trope for the boxing match. Bleichert has a plan to take a dive in the boxing match against Blanchard in order to gain enough money that he can pay to put his dementia-suffering Nazi father into a home for two or three years. He realizes he can beat Blanchard and plans to win the fight clean before losing cleanly to a KO... in the exact round he was supposed to take a dive.
  • Brewster's Millions, written in 1902 by George Barr McCutcheon. Brewster is set to inherit a vast fortune, but in order to receive the full amount, he must spend a large portion within a time limit and have absolutely nothing to show for it by the end. Many of Brewster's feverish attempts to waste money wind up unexpectedly making a profit.
  • The O. Henry story The Cop and the Anthem focuses on a hobo who intentionally tries to get arrested so as to go to jail during the winter by committing various petty crimes, all of which he fails to get arrested for. In the end when he contemplates cleaning up his life, a cop asks him what he's doing, and he responds "Nothing" which results in his being arrested for vagrancy and spending three months in jail.
  • Diary of a Wimpy Kid: After signing Greg up for basketball in Big Shot, Susan trades him to a rival team after discovering that he's terrible at it, hoping that his incompetence will cause them to lose against her own team. Cue Greg scoring the winning shot for his new team and celebrating his victory with them as Susan drives away with nothing but shame.
  • Dirk Gently's Holistic Detective Agency:
    • Dirk plans to make a completely wrong prediction of the contents of a university exam as part of a scam. He intentionally cultivates a reputation as a psychic by firmly denying that he is one, and dismissing rumors of the contrary as lies. Which rumors? The ones he started, of course. This is all so he'll get a chance to "prove" he's not psychic by predicting what will be on the exam, writing it up, having it sealed, and then revealing it after the exam has taken place. Then he fakes a family illness that requires raising a lot of money, and people start giving him "donations" for a peek at the predictions. In reality he just took a wild guess with the bare minimum of research, which he figures will be close enough to retain his mystique while avoiding any problems. Instead it turns out he was exactly right. To the very comma. He winds up going to jail.
    • By the sequel, his attempts to be a Phony Psychic becoming all too genuine are a Running Gag, as he tries to make vague pointless predictions and gets them all right. This ends with him standing on a rooftop, shaking his fist at the sky and yelling "Stop it!"
  • Dive (2003): Kaz, Star, Dante, and Adrianna apply for a summer internship of diving in the Caribbean and are baffled at being chosen out of thousands of applicants. Star is graceful in the water but has cerebral palsy that hampers her movements on land, and the other three have perhaps a dozen prior dives between them. It becomes clear that they have been selected by a trio of mysterious so-called scientists who don't want expert divers snooping around a shady treasure hunt that ultimately leads to at least one murder, although the four teens set out to make the treasure hunters sorry for their choice of patsies and find the treasure themselves.
  • Ender's Game: Tired of being built into a hero and having the fate of all humanity on his shoulders, Ender opts to win the final test by crossing the Moral Event Horizon, believing his superiors will never let him take command on a real battlefield after he does. Turns out that not only was this exactly what his superiors were hoping he would do, but the "test" was actually a real battle being fought by humanity without Ender's knowledge, and he just unknowingly won the war for the humans, committing genocide against the buggers in the process.
  • Percival Everett's novel Erasure has this after an avant-garde black novelist sells out. Infuriated by the roaring success of awful ghetto fiction that turns black people into caricatures, he writes My Pafology, the true story of Van Go Jenkins, a youth in the ghetto. He intended it to be a blatant parody: the book itself is incredibly awful, reproduced in its entirety and written completely in Ebonics. And then it hits the bestseller list and people start wanting to meet the (completely fictional) author who wrote such a "raw and stunning work." Oops.
  • In The Fountainhead, a client hires Howard Roark to design a really far-out type of resort, something really wild and different. The client had actually oversold shares in the resort, and because Roark had a reputation for having plans so unconventional that the public would never accept them, hired him with the intent of having the motel fail and thus be able to keep the money. However, Roark's design for setting up the motel as a camp with individual cottages becomes a tremendous success, ruining the unscrupulous promoters.
  • In Good Omens, Newton Pulsifer's ineptitude with electronics is such that when he tried to put together a joke electronics kit that wasn't supposed to do anything, the result started picking up Radio Moscow.
  • Happens in How NOT to be Popular by Jennifer Ziegler. Maggie attempts to make everyone hate her (or at least think she's weird) so that she won't form any attachments in her 10th high school. However, everything she does makes people like her more. For example, she decides to dress in ugly clothes from her parents' thrift shop, but ends up starting a new trend. Her parents come to school with her one day and her mother talks about how to keep your vagina tight, but all her female friends think she's cool for being so open minded. A guy even asks her on a date, and she starts political arguments with him over dinner, only for him to think it's interesting. She ends up being more of a Blithe Spirit to the school and a Manic Pixie Dream Girl to the guy.
  • The first Jack Reacher novel, Killing Floor, features this trope. The chief of detectives in Margrave, GA, Capt. Finlay, was going through a messy divorce when he interviewed for the job, and looked utterly incompetent. Since the Mayor and Police Chief are involved in the plot that's the centerpiece of the book, he's hired. Unfortunately for them, he's quite competent.
  • The first book of the Jesse Stone series by Robert B. Parker has the aldermen of Paradise, Massachusetts, hiring the self-destructively alcoholic Jesse Stone to be the new police chief, believing he will be easy to control. Unfortunately for them, he sees the new job as his last chance before his life gets completely ruined (as well as being self-aware enough to be suspicious that they hired him after he was drunk for the interview), and takes the opportunity to bring down their entire right-wing militia and swing the rest of the police force to his side.
  • John Putnam Thatcher: A passive version appears in Murder Without Icing. Unsuccessful entrepreneur Winthrop Holland tries to hide from his creditors by hanging around a losing hockey team that he owns a piece of, certain this will keep him below the radar. Then the team starts winning and he ends up being regularly mentioned in the sports pages of papers that some of his creditors read.
  • In one of the later Legion of the Damned books by William C. Dietz, the insectoid Ramanthians have invaded a world in the Clone Hegemony. The entire thing is meant as a distraction, to draw forces away from the true objective, Earth. However, to the surprise of everyone, the clone general in charge of the planet proves to be hopelessly incompetent, leading to the Ramanthians not only surviving, but holding the world against enemy attack. At one point, the Ramanthians even call the clone general "The best General we have."
  • In Don DeLillo's Libra, the Kennedy assassination is portrayed as a plot set in motion by an ex-CIA agent who intended it to fail so that the United States would be steered into a war with Cuba. Due to postmodernist confusion, somewhere along the line the "failing" part fell out of the equation, but the facts are so fractured and disjointed that no one will ever know for certain how that happened.
  • Emil of Lonneberga frequently gets sent to the tool shed as punishment for pranks. His little sister Ida eventually gets jealous, and decides that she wants to go to the tool shed, too. However, most of her attempted pranks backfire into nice actions, and when she eventually manages to commit one, it (of course) gets blamed on her older brother.
  • The Lost Metal: Due to investing in electrical companies right before Elendel's electrification, Wayne is now one of the richest men in the Basin. Believing that he is definitely not the kind of person to be trusted with money, he sets out to spend all his funds... only for everything he tries to end up making him even more money. For example, he tells his accountants to spend money on buying a lot of homes for poor people, and his affordable housing initiative ends up being a major moneymaker.
  • In book 1 of The Magisterium, The Iron Trial, the main character's father convinces him to fail on the entrance exam to the Magisterium, a school of magic. Unfortunately, he fails at failing.
  • The Man Who Knew Too Much: For complex reasons of Realpolitik, Henry Fisher needs to make sure that his own party's political candidate loses the election for a certain country district and the opposing candidate gets in. So when his younger brother suggests running for the position as an independent candidate on a platform of family land ownership, Henry approves the idea with vigor. He's taken aback when the idea of actually getting some property of their own turns out to be wildly popular with the constituency and the younger brother beats out both Party machines and takes the position in a landslide.
  • In Mrs. 'Arris Goes to Parliament, by Paul Gallico, the heroine of Mrs. 'Arris Goes To Paris decides to run for Parliament on the platform of "Live and let live". The (fictional) Center Party nominates her as part of a back-room deal, on the assumption that her candidacy is a joke and couldn't possibly succeed. Of course, she wins.
  • The Leonard Wibberley novel (later adapted into a Peter Sellers movie) The Mouse That Roared. Set in the years immediately following World War II, it's about a minuscule European nation, the Duchy of Grand Fenwick, that declares war on the US, planning to surrender and accept a bounty of post-war aid. Instead, the dozen-man invasion force accidentally wins the war by capturing a newly-made superweapon and its creator while strolling through a Manhattan evacuated for a nuclear drill.
    • In one of the sequels, The Mouse on Wall Street, Fenwick has become wealthy due to part of the settlement of the aforementioned war. However, the Duchess feels that this newfound wealth is corrupting Fenwick's idyllic lifestyle, so she sets out to lose it all on the stock market by picking stocks at random (by throwing darts at the financial section of the paper). However, when other Wall Street traders notice Fenwick is investing heavily in a particular stock, the traders conclude the Duchess must have inside information and immediately invest themselves, driving the price of that stock higher and earning Fenwick even more money. In the end, she sells off all the stocks for cash, has the cash shipped back to Fenwick, and secretly burns it.
    • Really, The Mouse fill-in-the-scenario book/film series ran on this trope. In The Mouse on the Moon, the Prime Minister of Grand Fenwick, desperate for indoor plumbing, tries to milk aid out of the US after their main export of wine has turned explosive by asking for cash for a space program. The US, seeing a cheap way to look like they are helping to make space international without doing something as stupid as actually helping another nation get an advantage over them in the space race by funding someone competent gives them a million dollars. Keen to top this, the Soviets send them an old rocket, which the PM plans to turn into a boiler for the new hot water system. The scientist from The Mouse That Roared discovers how to make an anti-gravity mix out of the explosive wine and without telling the PM that he is what he's doing, takes off successfully with the PM's son as co-pilot and beats the US and Soviets to the moon!
  • In MYTH Inc in Action, Guido and Nunzio infiltrate the Possiltum army to try and slow its aggressive expansion down. They get assigned to run a supply depot, where they use teamsters to ship things (which turn out to be faster and cheaper than the army's internal logistics division), send summer gear in response to a unit that had requested winter gear (turns out, the order was six months old so they needed summer gear by that point), sent propaganda material to a unit that requested toilet paper (considerably improving the unit's morale), and refused to do any paperwork (considerably increasing the amount of actual work they accomplished).
  • Double subverted in the Psych novel A Mind Is a Terrible Thing to Waste as a former high-school enemy of Shawn and Gus, now a millionaire, wants Shawn to use his "psychic" gifts to pick out good investments. Shawn does, but every investment goes bad and the guy reveals that he planned it this way in order to expose how Shawn is a fake psychic. This backfires on him, however, as his loyal assistant, who had believed Shawn's predictions, lost all his money investing in them and discovering that his boss did all this for a prank makes him murder the man.
  • In Pyramids, protagonist Pteppic is about to graduate from the Assassins' Guild school, but he realizes that he can't kill, so he attempts to fail his exam stylishly by aiming his crossbow at some completely random spot and firing. The shot richochets a couple times and hits the (dummy) target anyway, and the examiner passes him with a personal aside that he disapproves of these flashy modern methods.
  • In the Gordon Korman book Radio Fifth Grade, the school bully begins reading stories on the school's student-run radio show as part of an English project — horrific stories about pet kittens violently fighting each other. The student running the show is too intimidated to say they're terrible. When he finally gets the courage to say so, the bully admits he was intentionally writing bad stories and wanted someone to say so, so he could stop writing them.
  • In The Report Card by Andrew Clements, the main character Nora is a genius, but deliberately gets Ds on her report card, partly because she doesn't want to stand out, but also partly because she feels that report cards are a poor way of measuring the talent of students and is trying to prove a point. This strategy works great for her, until a man named Dr. Trindler has her take an I.Q. test. She tries the same tactic, not realizing that on this test answering just enough questions to get what would be considered a D on a school test is enough to make her a certified genius. She then later has to admit that she only got most of those questions wrong by doing so deliberately, revealing that she's far more intelligent than even what the test revealed.
  • Serge Storms':
    • In The Stingray Shuffle, a bookstore is really a front for a cocaine distribution ring hiding drugs in copies of a single obscure book, only for their constant ordering of new copies to get the book reprinted and back in the public eye. The "bookstore" staff the have to deal with the author coming for a book-signing, accompanied by camera crews and legitimate readers who want to buy autographed copies of the books.
    • In Shark Skin Suite, two law firms involved in a lawsuit against crooked bankers are secretly both business partners with the bank, and the plaintiffs' firm tries to throw the case by doing things like leaking information, assigning inexperienced or eccentric lawyers to try the case, keeping good witnesses off the stand and having bad witnesses testify. To their exasperation, the trial still goes in the plaintiffs' favor because their lawyers are far better than anyone realized (and eventually have Vigilante Man Serge providing behind-the-scenes help) and the defense lawyers are complete morons who make one mistake after another.
  • Star Wars: Joked about in an exchange from the New Jedi Order: Enemy Lines duology. Wedge Antilles is commanding the defense of a strategically important planet. He knows they can't hold it forever, so the strategy is to string along the enemy commander as long as possible by waging battles over unimportant goals, and make the Vong commander's moves predictable. However, during one of those battles, reinforcements for Wedge arrive ahead of schedule, resulting in the near-total annihilation of the Vong fleet along with their commander. This results in the Sorting Algorithm of Evil spitting out a far more competent leader to replace him, who will not be easy to predict, along with an even larger fleet.
    Wedge: Tycho, we're about to achieve a tremendous victory we don't want.
    Tycho: We'll put that in your biography. General Antilles was so good he couldn't fail when he tried to.
  • In Warbreaker, Lightsong plays a game that he doesn't know the rules to, but manages to win every time. He considers trying to throw the game, but realizes that would be identical to what he was already doing.

    Manhua 
  • There's an Old Master Q strip where the titular character somehow comes across a fake 100 dollar note in his posession, and decides he might as well lose it in his local mahjong joint. Unfortunately, he wins every single round, and ends up with THREE new fake 100 dollars.

    Music 
  • In the second part of Alice's Restaurant, a young Arlo Guthrie tries to get out of going to Vietnam by appearing psychologically unstable during his draft meeting. When he gets to the psychologist, Arlo says "Shrink, I wanna kill." He eventually starts jumping up and down, screaming "Kill! KILL!" All that does is impress the sergeant, sending Arlo further down the hall, with the sergeant saying "you're our boy!"

    Print Media 
  • This was the subject of an article in MAD called "The Rejection Slip", written and drawn by Saturday Evening Post cartoonist Tom Hudson. The premise of the gag is that Hudson has been rejected by so many other publications, but has not been rejected by MAD, so he submits a bunch of tired old gags to the magazine in hopes of getting a rejection slip. The editors instead end up approving every single one. Inspired by their approval to run his gags, he gives up on his pursuit of rejection slips, discards his entire collection, and submits ten gags to MADonly for them to reject every single one.

    Pro Wrestling 
  • After Ric Flair assumed leadership of the WWFnote , Vince McMahon had an episode long Villainous Breakdown, where he finally reveals that he intends to pull this trope and kill the business. He plans to inject a lethal dose of poison and do what killed WCW: bring in the nWo. He should have fired wrestlers like Stone Cold Steve Austin and The Rock.

    Puppet Shows 
  • Sesame Street:
    • In the direct-to-video release The Alphabet Game, contestant Gary Grouch participates on the game show "Alphabet Treasure Hunt" because he wants to lose (being a grouch), but keeps getting points by accident (when he's supposed to bring in something that begins with the letter B, for example, he decides to trash the place and brings in a trash can, which he points out does NOT start with the letter B, but inside the can are bugs, which DO start with B).
    • Similarly, in an earlier segment, Guy Smiley comes to Oscar's can to make him a contestant on "The Anything-In-The-World Prize Game". Oscar doesn't want to do the game, but his remarks following each question are mistaken for correct guesses.

    Radio 
  • In the Absolute Power (BBC) episode "Healthy Eating", Martin's friend Roger is a tax lawyer who opens a restaurant in Devon to lose money. However, he's relying on the out-of-the-way location to achieve this, since he's too proud of his cooking to actually offer bad food. Out of sheer mischief, Martin neglects to mention this to Charles, who surprisingly decides he wants to help (he thinks) a decent, honest man with a failing business. It's only after the wheeze is successful that he learns the truth.
    Charles: Let me get this straight. I've been slaving my guts out to get customers into this restaurant, and I've been wasting my time? You swine!
    Roger: You! You're responsible for these ghastly punters and peasants all over my tax dodge? You swine!
    Both: Martin!!
  • Bleak Expectations: When Bungling Inventor Harry Biscuit is turned into a (reluctant) evil zombie (It Makes Sense in Context), he begins inventing devices for Mr. Benevolent, but his friends and family are reassured because Harry's previous inventions have all inevitably failed. Unfortunately, this time around, all of Harry's inventions work perfectly.
  • In The Navy Lark, Sub-Lieutenant Leslie Phillips has a reputation of having done more damage to Royal Navy ships in one peacetime year (particularly HMS Troutbridge) than the Germans did during the entirety of World War Two. So, naturally, when Commander Povey needs a distraction to get away from his domineering mother in law, he strong-arms the Troutbridge crew into A Simple Plan: Let Phillips drive the ship and have him get intentionally into a minor nautical fender-bender, so that Povey would be compelled to go out and "investigate" (read: have a few too many pints). The one time, the sole time, Povey wants Phillips to do his usual bang-up job of navigation, this trope ensues. Phillips pilots the ship flawlessly, including circling another destroyer 42 times trying to ram it, failing even when the rest of the crew tries to sabotage the ship's steering to make a crash "inevitable". Then, Povey's mother-in-law gets laid up with the flu, and he is free to go. At this point, Phillips (still bringing the ship home) finally crashes full-speed into the dock.
  • Our Miss Brooks: In "School on Saturday", Mr. Conklin sends Miss Brooks to quell a mass student protest that arises when he opens Madison High School on Saturday, and demands everybody attend . . . .
    • Mr. Conklin hears from head of the board, Mr. Stone, that Conklin would be in trouble if he dared open the school Saturday. Stone was going to investigate, personally . . . .
    • Too bad for Mr. Conklin, Miss Brooks' speech to the angry teenagers convinced them to come in and attend class.
    • Mr. Conklin has Miss Brooks make another speech, to send the students home . . . .
    • Mr. Stone calls up, saying he's not going to inspect the school after all . . . .
    • Miss Brooks is sent to make yet another speech, and the students attend classes for the day. And stay in detention until 4:00 p.m.
    • Mr. Stone comes by late in the afternoon . . . more Hilarity Ensues.

    Tabletop Games 
  • In a published scenario for Teenage Mutant Ninja Turtles & Other Strangeness, a pair of villains try to reproduce The Producers scam, but by selling shares in a research facility with only one researcher, and he's a Mad Scientist. Unexpectedly he creates a successful bionic man.
  • In Warhammer, a dwarf that is dishonored becomes a trollslayer. His goal is to die in glorious battle going all-out against a troll (dwarfs take everything as Serious Business and cannot throw a fight). If he fails in this, because trolls are too small a threat, he becomes a Giantslayer. If he fails at that, the next step is The Dragon Slayer. The absolute bottom of the barrel for a Slayer is the path of the Demonslayer. All the while cursing because he keeps failing to die. Gotrek, the famous dwarf slayer of the Gotrek & Felix series, is a monstrous badass simply because the series would end if he ever fulfilled his oath. Fittingly, it took the end of the world to actually kill him. And then he promptly fought his way out of Hell, revealing even THAT didn't do the trick. And he's pissed.

    Video Games 
  • In A3, Itaru 'helps' Masumi with his love life (as Masumi has a huge crush on the director) with a dating sim. Said game is rigged in such a way that the wrong and perverted choices will make the love interest's (who Masumi changed to resemble the director) 'Affection level' go up. So when the actual director sees Masumi again, he tries out all of the wrong choices in real life, which was what Itaru was going for...only for the director to see it as hilarious and even asking if it's a new improv game.
  • Dead Island One the Playable Characters Sam B. is a rapper who is this trope in a nutshell. His one hit song "Who Do You Voodoo Bitch" was written on Halloween as a joke. Conversely all the songs he writes seriously fail miserably. Naturally he is very unhappy about this fact.
  • Dragon Age: Inquisition: Turns out, the whole main plot happened because one step of the Greater-Scope Villain's plan was a little too successful and interfered with the rest of it. Solas gave Corypheus the Orb of Fen'harel so that he could open it, since Solas expected doing that would kill whoever tried. Corypheus succeeded in opening it. In fact, he succeeded so well that he failed to die (or more accurately, he did die but Solas had managed to pick the one guy on Thedas with Resurrective Immortality) and was able to actually use the Orb for himself, forcing Solas to join your party to get it back and prevent Corypheus from destroying the world ahead of schedule.
  • In The Elder Scrolls III: Morrowind's Tribunal expansion, Tribunal deity Almalexia, who is also the Big Bad of the expansion, tries this by sending the Nerevarine to Sotha Sil's Clockwork City to die as a martyr for her cause, which is to establish a monotheistic state where only she is worshiped and only she is the savior of the people. This fails, she dies, and this failure leads to the eventual fall of the Tribunal Temple entirely.
  • Diona from Genshin Impact is such a good bartender that any drink she mixes is guaranteed to be exceptionally delicious, which is very at odds with her goal of ruining the wine industry by making terrible drinks. As shown in a particular route in her Hangout event, even when she deliberately messes up all the mixing steps and does the exact opposite of what a winemaker (i.e. Connor) did, the resulting beverage is anything but terrible; in fact, aforementioned winemaker has to admit the drink is a "true display of craftsmanship". It turns out she's stuck making supernaturally good alcohol because she was blessed by a fairy when she was a child.
  • Hypnospace Outlaw: The player eventually finds out that Counselor Ronnie was a troll account created by m1nx in an attempt to see how crappy they could make his content before Merchantsoft took notice. Merchantsoft took notice... and made him Teentopia's community leader. To make matters even more hysterical, he earns Merchantsoft a federal grant for promoting forward-thinking child-friendly content.
  • In The Legend of Kyrandia Book 3, the protagonist Malcolm is summoned by the Fish Queen for a game of Tic-Tac-Toe. Despite her enthusiasm for the game, she is exceptionally bad at it, and will always demand a rematch if Malcolm wins. Thus, you have to go out of your way to lose.
  • Mass Effect:
    • Thane, the dying repentant assassin of Mass Effect 2, willingly joins what is by all accounts a suicide mission to perform The Last Dance — he's dying of a terminal illness and wants to die doing something right for the galaxy. If you play your cards right, Thane can come through the suicide mission unharmed. If you take the time to gain his loyalty (and play your paragon cards right), you can reconnect him to his estranged son, giving him a reason to want to live till the end, if he survives. Subverted in the next game; if he survived the mission he gets his heroic end after all.
    • In Mass Effect: Andromeda, you at one point meet a guy who deliberately got himself assigned to a small, out-of-the-way chemistry lab due to being an introvert who wanted to be left alone. Unfortunately for him, people found out he has a bit of talent for brewing, leading them to think he was actually trying to set up a bar in said lab and bringing stuff to help get it up and running. Word spread about this "bar" and now the quiet, awkward introvert is spending all day serving drinks, placating drunks, and talking to people. He’s not happy about it.
  • In Medieval II: Total War, unlike its predecessor Rome, it is not possible to change your Faction Heir, presumably for historical accuracy. If the game decides that your Faction Heir is going to be that greedy, incompetent governor in the middle of nowhere instead of your kickass, utterly loyal and upright general, your only option is to arrange for your heir to die in a Uriah Gambit. However, if he survives, there is a good chance that he'll come away with a trait that will make him even harder to kill in the future. Good luck with that...
  • Big Boss, in the original Metal Gear, sends Solid Snake on a mission which he's assumed to fail. He doesn't, and Big Boss (really "Venom Snake", Big Boss' extremely-effective body double) gets a few rockets to the face for his trouble.
  • My Cafe has a storyline where Chloe is hired as a model, but discovers that the agency that hired her is abusive. Her contract won't allow her to immediately resign, so she tries to get herself fired by wearing clothes made out of trash when she's allowed to pick her own ensemble. Unfortunately, rather than criticizing her choice of clothing, the media applauds her for being eco-conscious. Rather than being fired, she gets promoted instead.
  • In the Nancy Drew game The Deadly Device, it's revealed that the killer is the same person who hired her. When asked why he hired her, he explains that Deirdre claimed that Nancy was an extremely incompetent detective, making him think that if he simply pointed her in the right direction, she'd half-ass her way through the investigation and arrest one of the other researchers whilst he got away scot free.
  • In the Overwatch comic "Going Legit", a businessman's employees have been kidnapped and held hostage by omnic terrorists and he hires two mercenaries to handle the matter discretely. The mercs... are Junkrat and Roadhog, two of the most loud, violent, and destructive criminals in the world. It turns out that there never was a hostage situation, the Suit hired the duo because he knew they'd rampage and destroy one of his buildings, which he was counting on to collect the insurance money while they took the fall. The problem is that Junkrat and Roadhog realize the deception, evade police capture, and kill the Suit in revenge.
  • In RuneScape, there's a low-level quest that basically gets you to fetch 3 odd items. Among them is a piece of burnt meat. You get burnt meat if you have unfavorable luck while trying to cook meat. Meat is one of the easiest things to cook successfully, and if your cooking level is above 10-20, there's a very slim chance to burn meat, which leaves many mid-high level players stuck and forced to buy burnt meat from someone else.
  • Episode 106 of Sam & Max: Freelance Police requires you to lose a game of Tic-Tac-Toe against a bunch of computers trying to create the most intelligent A.I. ever. Turns out the A.I. is actually very good — it just deliberately plays to lose, and the challenge is in forcing it to win against you.
  • In Town of Salem, the Jester's goal is to get lynched, so they try to spend the game looking as suspicious as possible. One common method is posing as an Investigator and randomly accusing another player of being evil, the idea being that once they're lynched and prove to be innocent, you'll look like a mafia member for trying to frame them. However, Jesters don't know who the mafia is either, so it's entirely possible that the person you choose actually is evil, meaning now people are convinced that you're important and should not be lynched, while the actual Mafia starts to gun for you (and the Jester loses if killed at night).

    Visual Novels 

    Web Animation 
  • In the Barbie: Life in the Dreamhouse episode "Bad Hair Day", Barbie takes her bad hair day and tries to turn it into a full-blown fashion disaster, in hopes of giving her rival Raquelle a spot in the sun for once. Being Barbie, she instead ends up starting a fashion trend.
  • Battle for Dream Island: Lollipop's Failure Gambit backfired when she tried to create the worst party for Four. Her party ended up becoming the best party instead.
  • Homestar Runner:
    • Part of the surprise ending of the cartoon "A Death-Defying Decemberween". After sledding down the Steep Deep, Homestar complains about his success, revealing that he had hoped to die in the attempt, so he could get out of visiting Marzipan's parents. And he only survived because Strong Bad, attempting to sabotage Homestar, removed the mattress Homestar had hidden at the bottom of the Steep Deep... not realizing that Homestar had filled said mattress with "hammers, broken glass, and candy canes sucked down 'til they're all pointy".
    • Strong Bad is sent an email from someone named "Sibbie" requesting that SB write a song about him. Strong Bad reacts badly, announcing "I will never ever ever ever ever write a song about Sibbie!", only to suddenly notice a hip-hop beat playing in the background; the Cheat is actually setting his rant to music. Soon Strong Bad finds that the "song" is a hit, being sung by Strong Sad and even played on the radio. SB loses his temper and screams "I freaking hate Sibbie!". Not five seconds after that, "I Freaking Hate Sibbie" starts playing on the radio.
  • Puffin Forest: In the Last Orders at the Yawning Portal Tavern video, Ben talks about a time when he was a dungeon master for a Dungeons and Dragons Epic, which is a game where multiple tables of players and dungeon masters all run the same adventure at once and work together to complete the story. Ben didn't like the fact that the game was partially competitive, with each table scoring a point whenever they found a clue to completing the story, because he thought that this would discourage tables from roleplaying and decided to avoid having his table be the one to win by running the game slowly and doing stuff to waste time. Somehow, Ben's table won by a very wide margin despite his efforts to slow his players down. Ben is very surprised and is unsure if they won because he is a fast DM, or if his players simply did a better job of working together than all the other tables.
  • In Red vs. Blue:
    • Project Freelancer intended the Reds and Blues to be too incompetent to accomplish anything but stalemate to serve as a training ground for the Freelancers. They probably weren't expecting the Blood Gulch Reds and Blues to succeed in killing three Freelancers (Two, Tex and Wyoming, while they were still Simulation Troopers, and the third, Maine, later after Project Freelancer was disbanded).
    • When the Blood Gulch Crew crash-land on the Planet Chorus, the Space Pirates conspire to split the troopers up among both sides of the civil war, hoping that the Reds and Blues' incompetence would speed up death rate of the False Flag Operation they have going. Thanks to Church and Carolina's interference and a few other factors, the sim-troopers not only figure out and expose the conspiracy, but manage to halt the plot completely.
  • In 2010, Yahtzee suggested that Square Enix were deliberately trying to tank their video game division and become a movie studio by releasing Final Fantasy XIII, which notoriously featured an an extremely linear story and limited player interactivity. It also sold millions of copies, was beloved by fans and showered with critical acclaim.

    Webcomics 
  • The Bruno the Bandit plot "Skeleton Crew" reports the writer's real life experiences at a software startup run as an investment fraud scam.
  • An interesting part fiction/part real example occurred in Dan and Mab's Furry Adventures, when a donation-war was declared between Bishōnen Incubus Abel, and enigmatic demoness Regina, with a full backstory going to the winner. Abel does NOT want to win. He REALLY doesn't. And for a while, he seems to be succeeding at failing. But some tension remains, and when the finally tally is revealed... well, let's just say that you can find the latest chapter of Abel's Story here. And considering the content, you really can't blame him for wanting it to remain private.
  • Dinosaur Comics: T-Rex tries to do something funny and instead accidentally finds himself with a job as a florist.
  • DM of the Rings features a D&D version of this: Aragorn is attempting to fall off the animal that he is riding. The GM rules that he needs to make a Riding roll to dismount. Aragorn rolls a critical failure, and assumes that this means he fell off. The GM decides that, since Aragorn was trying to fall, his failure means that he stays on the creature's back and rides it over a cliff (the in-game explanation is that his foot became entangled in the stirrups). This is discussed in the comments, where the author notes that if the player pisses off the DM enough (as Aragorn did, not long ago), anything they try to do tends to end up badly for them. This is also a Brick Joke, as earlier the DM had made a mental note to send Aragorn off a cliff.
  • In Drowtales, the side story of The Flower Queen explains how the titular queen, a dark elf in a kingdom made up mostly of drow, was prejudiced against the drow and tired of their attempts to woo her, so she set out an Impossible Task for a particular flower that existed in the ravaged old world, never expecting anyone to actually find it. However, one such knight did find a similar, but not exact, flower, but she was impressed enough by his tenacity that she kept her end of the bargain, and the two seem to have been quite happy for a time. Unfortunately, said flower turned out to be a parasite that eventually killed her and the entire city, and the Knight's last known actions were trying to track down the person who directed him to the flower so he could take revenge on them, and then murder the sentient tree that gave him the soul parasites instead of letting him adopt her children. Oops.
  • Freefall has a case of two separate parties trying to make the other suffer this trope. Florence has saved the Pointy-Haired Boss known as Mr. Kornada from a collapsing building, along with his robots Qwerty and Dvorak; in the process, she's ended up in the water, during a hurricane. Sam initially intends to take Kornada where he wants to go for a fee, but Helix's suggestion causes him to get hit with a sudden strike of conscience, and he decides to go save Florence. When Kornada hears about this, he "convinces" his robots that he's suffering a heart attack, and as he's human and Florence is not, the robots' safeguards prioritize saving him, even if they have to wrest control of the ship from Sam. The robots win, Kornada's fake heart attack gets revealed, and Sam doesn't get paid.
    Qwerty: We've got to get Mr. Kornada to the spaceport!
    Sam: That's what I want to do! But I have to rescue Florence before she drowns!
    Qwerty, Dvorak, Helix: That's what we want to do!
    (cut to Sam holding onto the captain's chair while Qwerty and Dvorak try to pull him away and Helix pries at his fingers)
    Helix: (thinking) This battle would be much more intense if both side weren't trying to lose.
    Qwerty: Oh no! I've got his legs! Hurry, get Sam a wrench so he can club me!
  • El Goonish Shive:
  • Karin-dou 4koma: Kinka challenges Tamaryu to a Yu-Gi-Oh! card game with the intention of going easy on her, but she ends up crushing Tamaryu because her hands instinctively cheat. Ginka—who doesn't even know how to play and makes a deck out of whatever catches her eyes—takes over to cheer Tamaryu up, but also ends up crushing Tamaryu because her great luck keeps giving her good cards.
  • In Life (2012), to Lex's consternation. when he sends 'Edward' to go ask Madison out, Madison doesn't say no.
  • In 2000, Llewellyn of Ozy and Millie ran for president on the People With Nothing Better To Do ticket on a lark. Since he doesn't actually want the job, he then runs the most idiotic campaign imaginable — his running mate is a stack of pancakes, and his platform centered around banning bread and selling Arizona and New Mexico to Mexico and using the money to buy British Columbia from Canada. Thanks to confusing ballots, he ends up neck-and-neck with Bush and Gore, and is ultimately forced to withdraw from the election in order to get out of becoming president, causing the papers to announce "CANDIDATE DOES NOT ACT LIKE TWIT: We picked the wrong one, say voters."
  • Something*Positive has an arc where a man applies for a job at Aubrey's nerd phone sex line, expecting to be rejected out of hand and gaining material for a sex discrimination lawsuit. Aubrey promptly hires him to deal with Nerdrotica's growing gay male customer base. This outcome is a bit of a subversion, as the reason he was attempting this scam is that he had been unable to get a regular job, and this was all he could figure out to do. While it isn't exactly his dream job, it's a decently-paying job, and he sticks with it.

    Web Original 
  • In the Achievement Hunter series GO! episode #74, the mission is to see who can fly the longest in Grand Theft Auto. Ryan Haywood made his intent known to be the first to lose due to an infamous meme of his note . However, not only does he win, the first thing out of anyone's mouth is Michael screaming "RYAN'S STILL IN THE AIR!"
  • Mega64 created a video detailing a fictional history of video game developer Hironobu Sakaguchi's attempts to bomb the Final Fantasy franchise in order to follow his true passion: becoming a rap star. The only thing that works? Final Fantasy: The Spirits Within.


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