In Harry Potter and the Half-Blood Prince, a Potions lesson has Slughorn presenting a mystery poison to the class and the students must concoct an antidote based on the contents of the potion. Harry, who has been receiving help from the Prince's annotations, realizes there's no real foolproof cheat around this (as Hermione also gleefully remarks on), so he grabs a bezoar from the cabinet and presents that as his antidote. Slughorn rewards him 10 points for "sheer cheek." None of his classmates are amused.
Ug the Unreliable, a notorious goblin con-artist, pulled this in his most famous con. He set up a Demiguise Derby (keep in mind that the Demiguise is an animal whose hair is used to make Invisibility Cloaks) and got away with a ton of gold.
Older Than Feudalism example in The Bible: In Habakkuk 1:5 "Look among the nations, and see; wonder and be astounded. For I am doing such a thing in your days that you would not believe even I if told you."
Dirk Gently fuses it with Bavarian Fire Drill in Dirk Gently's Holistic Detective Agency when he walks into a police-packed crime scene, then orders one cop to disassemble a wastebasket and another to guard the sofa stuck halfway up the stairs (which the cop in question had been ordered to saw up and remove).
Dirk Gently tries to employ this trope in The Long Dark Tea-Time of the Soul, when he steals a cup of coffee off a woman's table in a cafe, believing the act will be so shocking to her that she would let it go without comment. It doesn't work.
In So Long, and Thanks for All the Fish, Arthur Dent buys a package of biscuitsnote that is, cookies, if you're American and sits down at a table at a train station. A complete stranger sits down next to him, opens the package of biscuits, and eats one. It starts out as this trope, with Arthur who indeed so shocked that he does not comment at the audacity of the man who has opened his biscuits and eaten one. Instead he escalates it into a battle of wills, each man taking turns eating a biscuit until they're all gone, with nary a word spoken. After the other man leaves, Arthur gets up and finds his own packet of biscuits—they were underneath his newspaper the whole time. The biscuits were the other man's. This reportedly happened to the author (but see thisSnopes page).
To pitch this story Adams related it to discredited politician and convicted liar Jeffrey Archer, who promptly used it in one of his own books and claimed he'd thought of it first. Adams was inclined to be generous, putting it down to a misunderstanding, although other writers have also complained about Archer allegedly stealing their plot bunnies. ("Allegedly" used as a legal disclaimer here in the Have I Got News for You sense.) Satirical magazine Private Eye related the tale of Archer sitting on a judging panel for new short fiction by unpublished writers and using it as a chance to steal their best ideas to use himself—then, in the days before his own downfall for fraud and lying on oath,he used his lawyers to threaten those who complained at this breach of trust with actions for defaming his character, in daring to allege he'd do such a thing.
Vorkosigan Saga: Miles Vorkosigan is completely unafraid to run with this, as part of his Guile Hero approach to pretty much everything:
In The Vor Game, he has to get back a hostage from the villain before she kills the hostage. At the appointed meeting place, he and his men burst in, guns drawn, and threaten to shoot the hostage if she doesn't give in to Miles's demands. The villain has no idea what to do when faced with the very threat she was about to make, and so Miles gains the upper hand.
Gregor (the hostage) doesn't do so badly himself: saying, "No, he's bluffing. Watch!" and then walking right up to the muzzle of a plasma cannon held by one of Miles's people, allowing Miles to slam the blast doors behind him.
Miles's speech to Cavilo right before also counts—Elena's reaction: "did you in fact just connive to assassinate Gregor in one breath, offer to cuckold him in the next, accuse your father of homosexuality, suggest a patricidal plot against him, and league yourself with Cavilo?"
In The Warrior's Apprentice Miles takes control of a mercenary fleet on the pretext that he is part of a super secret elite mercenary outfit. Specifically, he captures a small vessel and offers the crew membership in his fictional mercenary outfit. He then uses that vessel as additional proof of the existence of said mercenary outfit. Before long, he's created a super secret elite mercenary outfit, composed entirely of people thinking they were joining an existing super secret mercenary outfit.
In Memory, Miles dons all his medals before going to ask the Emperor of Barrayar for a favor — including his Cetagandan Order of Merit. The Barrayaran Empire has been at war with the Cetagandans three times by this point, has come close to a fourth (in the Hegen Hub) and has actively worked against them in their conquest of another planet (the Dagoola IV operation). Emperor Gregor's reaction? "Good god, Miles. I've never before seen you come the Vor Lord with intent."
In Captain Vorpatril's Alliance, the Cordonahs asking for 10% of the profits of a cache of stolen property below ImpSec Headquarters as a finders fee, while on trial for (among much else) sinking ImpSec Headquarters.
In Brothers in Arms Miles also gets his real clone brother Mark to pretend to be a different, non-existent, clone brother to fool some Cetagandans.
Roald Dahl's Matilda explicitly states that the monstrous headmistress Agatha Trunchbull would not get away with being cruel and abusive anywhere else, but she gets away with using a girl for human hammer throwing, flinging kids out of windows and locking them in a torture device because no parent would believe a child trying to tell on her. Dahl knew his stuff—his intended audience (elementary-school kids) were perfectly capable of buying that explanation. This It is Truth in Television. The Trunchbull was based on Dahl's personal abuse in the British school system. A full account can be read in "Boy"—St. Peter's was not a happy place and the matron was an inventive taskmaster.
"Never do anything by halves if you want to get away with it. Be outrageous. Go the whole hog. Make sure everything you do is so completely crazy it's unbelievable."
In David Gemmel's "Legend". Staring down an impossibly massive horde of Mongel expys who hold his castle under siege, with most of their walls having already fallen, no sign of help on the horizon, only a few hundred troops and their most powerful warrior dead, Rek could have surrendered or fled with honor. In fact, he had already given his troops that option. So, what does he do? Flee? Surrender? Never. He kits himself out in full battle rattle and invites his officers to dinner... inside the enemy camp... where they will give Druss a magnificent sendoff worth of a hero. Not only does it WORK, but Rek spends the night talking to their leader, Ulrik, about their respective visions for the future and their pasts.
Francis Crawford of Lymond does this all the time in Dorothy Dunnett's Lymond Chronicles. One of his better moments is chasing away an English army by dressing several thousand Scottish sheep in metal helmets on a foggy day. The English see the reflections from the helmets and assume the Scottish have a bigger army, even though there's only a few Scottish soldiers. He also pulls off a lot of disguises because they're so outrageous that no one would guess they're him, including a tearful Scottish whore, a flamboyant Spanish nobleman, a drunken Irish bard, and a French falsetto singer.
In Joseph Heller's Catch-22, Milo Minderbinder corners the market in Egyptian cotton. Unfortunately for him, he discovers he can't find a buyer for it. Yossarian tells him to bribe the US government into buying it. When he asks how, Yossarian replies that if he makes the bribe big enough and spreads the word, the right person will contact him. If questioned, just tell people that the national security of the USA depends on a strong Egyptian cotton industry. Be straightforward and act like you are doing nothing wrong and it will work. Sadly, this has also worked in Real Life.
This quote by Colonel Korn, spoken in justification of awarding bombardier Yossarian a medal for going over his target twice after failing to drop his bombs the first time: "You know, that might be the answer—to act boastfully about something we ought to be ashamed of. That's a trick that never seems to fail."
Moist von Lipwig from Terry Pratchett's Discworld series does this all the time.
He claims If I am going to fail, I would rather fail spectacularly,.
Tolliver Groat: You've got to learn to walk before you try to run, sir! Moist: No! Never say that, Tolliver! Never! Run before you walk! Fly before you crawl! ...all or nothing, Mr. Groat!
Making Money featured the most gloriously audacious moment of his entire career to screw over a blackmailer. Said blackmailer is threatening to expose the fact that Moist was a crook. so what does he do? He gets on the stand in front of the entire city and admits it.
As he waited for this crucial moment, he witnessed a cute dog named Mr. Fusspot come skirting out behind a curtain in to the middle of the room chasing after and wanting to chew a thick leather vibrating dildo. No one dare bat an eye at it. Moist decided if he lived in a world where that can happen and be accepted, he can do what he does in the above idea.
Moist von Lipwig: "You get a wonderful view from the point of no return."
Pick a Night Watch book, any book with the Watch and you'll find this, usually committed by Carrot or Vimes:
Carrot gets away with this a lot by being himself. You can't help but do what he wants, and like him anyway.
Carrot brushed the dust off his hands and smiled at everyone. The trolls looked puzzled. In theory, Carrot was just a thin film of grease on the street, but somehow it didn't seem to be happening...
Angua: "He just called a hundred trolls 'good chaps.' Some of them are just down off the mountains! Some of them have still got lichen on them!"
Nobby: "Funny, that. If we was to try it, we'd be little bits of mince. But it seems to work for him."
Vimes' disarming of a riot in Night Watch: He goes outside the watch house, unarmed, with a Powder Keg Crowd forming and sits down on the front porch drinking cocoa and smoking a cigar. He makes very sure everyone can see that both his hands are full and neither hand has a weapon.
Guards! Guards!!. The 4 Night Watch members get a long way into the Shades, a district of Ankh-Morpork so dangerous that assassins are afraid of going in, and avoid death by being loudly drunk, confusing the criminals tailing them. They later arrest someone for committing murder with a blunt instrument. Said blunt instrument was a forty-foot dragon. In fact, the dragon is also arrested.
Carrot's very good at taking laws literally. He accuses someone trying to dismiss a golem as littering.
Vimes Lampshades his own use of this trope in Thud!:
Vetinari: What would you do if I asked you an outright question, Vimes?
Vimes: I'd tell you a downright lie, sir.
In Carpe Jugulum, Count de Magpyr (an evil vampire) confronts the peasant mob with critical appraisal of their weapons, and promises to send out snacks later. Then he goes back into the castle trailed by "the puzzled mumbling of players who have had their ball confiscated."
In Jingo, two armies are about to fight a battle. When Commander Vimes protests that they can't be arrested, Carrot does not see why not. They could charge them with Action Likely to Cause a Breach of Peace. He then does it successfully and among other charges: Loitering with Intent, and Loitering within Tentnote "Hah!", one count of offensive language for the commanding general who protests this (this is commanding officer of Vimes' own city by the way) and Carrying Concealed Weapons because he isn't looking at the weapons at the time.
Also in Jingo, Vimes insults a member of the nobility loudly, repeatedly and to his face, because he knows Lord Rust's worldview does not admit the possibility of such a thing and Rust, therefore, will not notice.
In The Last Hero, Commander Vimes sends him to arrest Cohen the Barbarian and his Silver Horde, who may accidentally blow up the world. The charge? Conspiracy to cause an affray.
During a search, Carrot had been ordered to leave as soon as Dr. Whiteface, the head of the Fools' Guild, told him to. When Whiteface confronted him: "If you tell me to leave, I'm going to have to follow the order I was given. Isn't that right, Sergeant? I really don't want to have to follow that order. *leans in closer to Whiteface* If it will make you feel better, I shall probably feel a little ashamed afterward." When Dr. Whiteface threatens that he can have a dozen men in there in moments, Carrot tells him that doing so would only make it easier for him to obey his orders. In the process, Carrot utterly astonishes Sergeant Colon, who has himself attempted some fairly audacious plans (such as guarding a bridge in case people tried to steal it, and then justifying this): "Sergeant Colon was lost in admiration. He'd seen people bluff on a bad hand, but he'd never seen anyone bluff with no cards."
He arrested the head of the Thieves' Guild by simply walking inside and taking him away. (This was before he knew that the Thieves' Guild is a perfectly legal institution.)
Susan Sto Helit, grand-daughter of Death does it too. When employed as a nanny, she quells her charges' fear of a monster in the darkness by taking an iron poker and beating it stupid. The children's parents assume she's putting on a show. The monsters know better.
Cohen qualifies, too. At one point, he explains to a group of soldiers that they aren't as scary as they could be, and reminds them of "the element of SURPRISE!" before slaughtering them all in five seconds. In Interesting Times he intends to steal the entire Agatean Empire. The idea is so audacious that nobody thought to defend against such a plan and it works flawlessly.
Rincewind exploits this trope in The Science Of Discworld III, when he must prevent Charles Darwin from being stung to death by wasps. Realizing he has to be visible if he's to distract the wasps, he dresses up in a green wig, a red clown's nose, and a pink tutu; Darwin will either refuse to believe his eyes or will never admit to seeing something so outlandish.
The presence of Dr Hix, a necromancer, at Unseen University, despite the fact that necromancy is outlawed. If he skulked around the premises and tried to hide what he does, he would certainly be drummed out. Instead, he is openly there—they just renamed the position the "Department of Post-Mortem Communications." He has an animated skeleton advising him. As a corollary, Dr Hix is contractually obligated to provide a modest and acceptable level of dissent and evil. At some point the thing is tipped over into Refuge in Audacity territory, much to the astonishment of visitors. There is also a legal reason for this; If there is a legal, official "bad" wizard in the area then part of his job is enforcing the monopoly with fireballs.
This also explains the Librarian's presence, along with him being "the best Librarian we've ever had." The Librarian was turned into an orangutan two books in and has stayed this way willingly ever since.
Employed frequently by Patrick Bateman in American Psycho. For example when he drags a dead, hacked up body in a sleeping bag out of his apartment, through the lobby, and onto the street in full view of several people. He heaves it into the back seat of a cab and takes it to his other apartment uptown to destroy it.
In Black Legion, this is the selling point of the plan to attack Harmony—after all, who would believe that less than two hundred warriors, vast majority of which are mindless, soulless undead, would attack Emperor's Children's second most fortified stronghold?
P. G. Wodehouse's popular character Psmith. Psmith becomes a socialist because he believes in the redistribution of property—his particular brand of socialism involves his redistributing other's property to himself. When he seeks employment, he offers to provide any service, including assassinating someone's aunt.
Tavi (a captain in the Legion at the time) disobeys a direct order given by a commanding officer who would love to have an excuse to have Tavi removed from command, breaks into the strongest prison in the country to free the a leader of the enemy Canim, and brokers a truce with them, again against orders. How does he get out of it? He proposes to the First Lord ( his grandfather) an amnesty for his former countrymen who served the Canim in certain unusual circumstances, but it's phrased in such a way that it would apply to himself as well.
Later, he has to deal with the Icemen, a race of telepathic yetis living in the lands north of Alera. They've been at war with Alera for hundreds of years and constantly attempt to get control of the Shieldwall, a massive fortress stretching across the border which was created to keep them out. Tavi does not need this distracting him, since the Horde of Alien Locusts have eaten half the continent. His solution? give the Icemen the Shieldwall, then rent it back from them.
Stopping Ambassador Varg from visiting Gaius Sextus was a textbook example. How do you stop an 8-foot tall, 700-year-old wolfman from kicking your eldritch-deprived ass? Pull a knife on him.
In the finale, (in the heat of combat), Kitai finds him by assuming that he's going to be in the most dangerous place she can imagine, doing the most foolish thing possible. She follows him because she also assumes it's going to work.
In Silverfall lady Qilue attends a Nobel's costume party, without an invitation, for the purposes of spying on the attendees. She can't disguise herself with magic, so instead arrives as herself wearing a very revealing dress. The only person who notices she's a real drow is a high-ranked Harper spy, and he almost fell for her anyway.
Liriel Baenre walks openly through Waterdeep simply by joining a host of masquerading nobles and relying on being viewed as yet another decadent reveler glamoured to look like a Drow.
Tzigone from Counselors and Kings was accosted by one of the members of a martial orderwhile wearing stolen clothes and medallion of said order for behavior inappropriate to a member of the order? She took offense, loudly, at being mistaken for one of them in the first place and got away with it.
Lauzoril, Zulkir of Enchantment—the only high-ranked Red Wizard who didn't try to hide from the scrying of their scourge The Simbul, later faced her, made his own separate peace, all the while praising the trade rivalry it brings them. All this after waging war on her land and her agents for years and sending assassins after her sister—which is more than most Red Wizards she slain could claim.
Cayleb Ahrmahk is fond of using this to his advantage, such as chasing down an enemy fleet of ships in what should have been near impossible conditions purely for the added shock value their arrival would cause.
A Mighty Fortress, has Madame Ahnzhelyk Phonda. Besides running a long standing spy network right under the nose of a Corrupt Church and its paranoid Grand Inquisitor there is her solution for smuggling more than two hundred potential Inquisition victims to safety: hide them in ships whose paperwork claims they're shipping items for that very same paranoid Grand Inquisitor to guarantee no one would dare examine things too closely. Cayleb is described as being "almost reverent" when he finds out about it.
In the Dale Brown novel Flight of the Old Dog, the heroes, running out of fuel for their Cool Plane, land at a semi-abandoned Soviet airbase to get fuel. They do something similar in Plan of Attack.
Harry Dresden's plans sometimes work because no one ever thought to protect against such an outlandish possibility. Harry exists within the margins of likelihood.
In Dead Beat Harry is in dire straits as several necromancers are planning to invoke a spell to turn one of them into a minor god. He is stuck on the other side of town and cannot break any laws of magic, even if it is to save the word, which includes raising human undead to fight. His solution: Resurrect a 65 million year old T-Rex and ride her into battle. As she isn't human, technically he didn't break the law and he saves the day.
In Small Favor Harry is facing down a magical assassin who has killed three archmages and took their stoles as trophies. Harry couldn't beat him in a fight and both know it. But Harry is owed a debt by the assassin's court and to be killed before calling it in would dishonor the assassin's queen. So, he allows Harry to name the favor, short of calling off the order to kill Harry. Harry wants a real freshly baked doughnut. It's a stall, as both know this, but by the time of delivery, the reason for the hit will have ended and Harry will be safe, but the assassin goes through with it. It becomes a humorous story where the assassin came from..
Turn Coat: Challenging the White Council to a duel. It allowed Harry to sneak his real gambit past, because everyone was so busy washing their pants.
When he showed up to a masquerade ball thrown by Red Court vampires... dressed as a cheesy, B-movie parody of a vampire, complete with cheap tuxedo, high-collared cape, and plastic fangs. The deliberate insult nearly got him violently dismembered by incredulous vampires.
His fairy godmother wants to capture him and turn him into one of her hounds for his own protection. One time, on a mission, he and his companions must travel close to her domain and risk being caught. He gets caught, but escapes by one means: eating a poisonous mushroom that will kill him. Happily, one of his companions has the cure on hand and will trade it to the godmother in exchange for letting Harry go this night.
In one short story, after finding out that an archangel had arranged to makes sure Harry ended up being in the right place at the right time to help out with a specific case. He proceeds to try and bill the archangel for services rendered. Though, Harry does have limits as he isn't prideful enough to give the bill to the Lord Almighty.
Serge Storms, lead character of the Florida Roadkill novels, avoids attention by attracting attention to himself. In the first novel, he gets a dead woman out of his hotel room by dressing her up in a form-fitting kevlar bodysuit, a Spider-man mask, and a strap-on, and he and his friend walk her out the door. Everyone assumes that they're taking a drunk friend home after a truly spectacular party.
In The Hound of the Baskervilles, a suspect is spotted spying on 221B Baker Street from a cab. Holmes and Watson unsuccessfully attempt to intercept it, then track down the cabdriver the next day to ask about his passenger. The cabman informs them that the rider had claimed to be a detective... and had gone by the name of "Sherlock Holmes". Recognizing this trope at its finest, the real Holmes bursts out laughing when he hears this, and never does correct the cabman as to his own identity.
Later in the Charles Augustus Milverton story, when Lestrade is looking for the two (ultimately innocent) suspects of murdering the title character, Sherlock Holmes points out to Lestrade that the description of one of the suspects may fit that of John Watson. They laugh it off, without Lestrade ever realizing that Holmes and Watson are actually those two suspects.
In L. Jagi Lamplighter's, Prospero Lost, Astreus persuades Miranda to dance with him after he had publically insulted her by pointing out that if they dance, everyone will assume that she had rebuffed him, and be eager to dance with her to hear about the reconciliation. She points out that they didn't reconcile; he points out she doesn't have to tell them that.
Invoked in Neal Stephenson's Zodiac, when Sangamon notes that Gomez would never believe him if he said that Alkali Lane's pH of 13 is a hundred thousand times higher than is legal. So he tells Gomez it's "more than twice the legal limit", which is both technically true and credible.
Sandy Mitchell's Ciaphas Cain novels. At the beginning of For The Emperor Cain, THE HERO OF THE IMPERIUM, deliberately invokes this trope when confronted by a mess hall of rioting Guardsmen by leaping up onto a table, pointing at someone, and ordering them to get a mop. The bloodstains were deplorable. In Echoes of the Tomb, he runs into a portal to parts unknown because he believes possible death at the hands of whatever's on the other side is preferable to certain death due to the Necrons before him.
The Traitor's Hand proved this tactic only works for protagonists. When Cain is attacked by a horde of half-naked cultists who fight over who gets to die at his hands first and giggle as he cuts their limbs off, he notes the sheer insanity of it all as he continues to mow them down without pause.
In Lee Lightner's Space Wolf novel Wolf's Honour, Ragnor realizes, fighting with Madox, that Madox will unquestionably wear him down with minor wounds that add up to mortally injured. So when Madox strikes at him, he doesn't defend himself. In fact, he drives the sword deeper in, and Madox can't pull it out and so can't parry when Ragnor strikes with the Spear of Russ.
In James Swallow's novel Deus Encarmine, the Blood Angels are reduced to a small fraction of their number, facing a Last Stand, and on the verge of despair. Arkio proposes that they sneak into the port they had to abandon and turn its guns, not on the forces facing them, but on their spaceship.
Lady Cecilia from Elizabeth Moon's Heris Serrano Trilogy. An old lady who owns a space yacht called Sweet Delight, decides to impersonate a military officer. She does this by declaring herself to be a high-ranking agent on a mission too secret for the rank-and-file crew to know about, and responding to any requests for proof with a Death Glare and vaguely-worded threat. It's so outrageous that everyone assumes there's no way she could be just making it up. This is a deconstructed example because he captain and most of the crew of Lady Cecelia's yacht really were military personnel undercover on a top-secret mission... even if they all thought they'd been discharged.
In Plan B, a book from the Liaden Universe, the clan motto of Clan Korval is "I Dare." This story features our heroes planning to steal aircraft from the invading army. In the process they referencethis trope:
It was a plan somewhat short on detail, but Nelirikk never doubted it would succeed. It was much too audacious to fail.
Ken Follett's The Pillars of the Earth: Bishop-to-be Waleran getting Prior Philip to pledge support for his nomination when the current Bishop died, then casually announcing the death of the then-Bishop. Among Philip's reasons for never reporting this to anyone is that noone would believe a man of God would do something like that.
In Romance of the Three Kingdoms, Zhuge Liang was forced to defend Xicheng with 5000 troops, half of which had to be reassigned to help evacuate all of the goods from Xicheng. When a giant Wei army appears, there was no refuge left but audacity: he appeared over top of the open city gates playing an instrument, flanked by boys holding burning incense, while soldiers dressed as peasants opened all the gates of the wide open and started sweeping them out. Wei army commander Sima Yi orders a retreat. Sima's sons were convinced that it was a bluff, but Sima himself thought (from previous encounters) that Zhuge didn't take risks, and that there must be some deep strategem behind this display. To Sima's credit, Zhuge comments afterwards about how much he hated having to take a risk in this instance, but it simply couldn't be helped.
Fight Club: the Narrator beats himself up in the office of the manager from one of his waitering jobs. Seeing as there was no way it could be explained to security without sounding crazy, between this and some incriminating evidence, he manages to secure himself a constant paycheck to fund fight club.
Invoked in Tomorrow: When the War Began, in Ellie's plan to get Lee, who can't walk thanks to a gunshot wound to the leg, out of enemy-occupied Wirrawee. "Maybe we're going about this the wrong way. We're thinking of little, quiet, sneaky things. We could go to the other extreme, rock up in something so indestructable that we didn't give a damn who saw or heard us." They proceed to steal an excavator and escape hiding Lee in the shovel, hitting several cars and killing a few enemy soldiers on the way.
In the world of Atlas Shrugged, every last move of every businessman is followed by a Shadow Dictator, so how could one of the most successful businessmen destroy his multinational enterprise? Become the most worthless playboy and invest millions of dollars in a project he admitted knowing was worthless and publicly announcing that he would enjoy watching the farce unroll.
Tyrion Lannister's list of "crimes" he admits to while imprisoned at the Eyrie. At another time he outright threatens to kill one of the king's bodyguards, in the middle of court, in front of the king, and gets away with it. This backfires badly on him when he is accused of killing Joffrey. Everything he said and did in King's Landing that he got away with earlier, is thrown back at him in a big hoop, taken out of context.
Tyrion's brother uses this trope as well. Upon returning to King's Landing in the third book, his first act is to walk right into the holiest cathedral in the land, where the corpse of the King (and his own child-by-incest) is lying, and send all the priests away so he can have some alone time with his sister right there. She's menstruating at the time too, just to add to it.
Lord Wyman Manderly, you sneaky, dramatically darkGuile Anti-Hero, you. Where to start? Two words: Frey Pie. Taking time to plot revenge against an entire family is pretty usual in this series. Killing people under the radar? Standard practice if you've got half a synapse working. Killing three of that family undetected and totally to the letter of unwritten social convention, baking them in massive pies, preceding to offer them as a "gift", along with other provisions, at a wedding feast (so, technically, you haven't even accepted their salt—just to be sure), while requesting a folk-song commemorating a very similar revenge-plot as you watch your other, future targets chow down while you're busily ploughing through massive portions yourself, not just so they'll eat up unsuspecting? Audacious, bro! And, he hasn't even finished with his whole plan, yet! All this while hiding behind your Big Fun, Fat Idiot persona and to get revenge for not just their breach of Sacred Hospitality, but some deaths of your own family members and liege lord? It's hard to know whether to throw up, wince at what's coming, stand up and applaud... or all of them at once.
Fear and Loathing in Las Vegas: "The only hope now, I felt, was the possibility that we’d gone to such excess, with our gig, that nobody in a position to bring the hammer down on us could possibly believe it." This was his stylistic signature. Memorably in his coverage of the '74 presidential campaign he devotes a solid half page to his desire to mace and cattle prod the first available politician while running them nude down main street with a bell around their neck.
The Plan to distract Sauron from Frodo's quest by marching the battered armies of Gondor and Rohan into a direct assault on the Black Gate relies heavily on its sheer audacity to fool Sauron into thinking Aragorn has the Ring.
In Claudius The God, Herod Agrippa, grandson of Herod the Great, uses audicity to defend himself in his schemes, such as relating stories about his (mis)adventures to Claudius' mother, Antonia who, being a prim and proper Roman matron, is "shocked" by his tales.
How do you get into the University when you're flat-out broke? If you're Kvothe, you sneak in, spy on the professors, and then ask them to pay you to attend.
How do you destroy a voodoo doll of yourself that your rival has? Naturally, you just walk into his rooms but you can't just do that when he's there, so you lure him out with a pretty girl, walk in, destroy it, and get caught saving your rival's stuff from the fire. For this plan to work, his rooms have to catch fire...
R has to sneak into the humans' stadium encampment. So he gets together a group of friends, and runs right up to the stadium gates, pretending to be a Living man getting chased by zombies. Predictably, the guards rush the "victim" to safety with no questions asked. He decides later that it only worked because no one had ever thought to try it before, or considered that zombies could mimic the Living.
Similarly, R's plan to save Julie by pretending that she's a new zombie convert works because no zombie has ever considered keeping a Living human as anything other than "eat later" food.
1632: The Real Lifecoup de théâtre that Cardinal Mazarini pulled off as part of the settlement of the War of the Mantuan Succession, riding between two warring parties waving a blank piece of paper and saying it was the formal settlement document for the war to buy time for the real thing to be finished, is referenced in the novella Between the Armies and in 1634: The Galileo Affair.
In When the Tide Rises, Daniel Leary mounts a raid on the home star system of the Alliance of Free Stars, relying in part on the notion that because no one would expect anyone to attack the star system with just an antiquated light cruiser and a corvette, there wouldn't be prepared plans available to handle such a situation.
In the epilogue, the Haven ship supporting the local insurrection was destroyed. Haven tried Honor in absentia for killing off a civilian freighter and crew. It was even lampshaded that the reason the Havenite people would believe that is because it would simply be too big of a lie to be taken as a falsehood.
In The Girl with the Dragon Tattoo, after Blomkvist realizes that Salander hacked his computer, he decides to recruit her to help him investigate the disappearance of Harriet Vanger. Rather than recruit her through her employer (who is highly protective of her) Blomkvist decides to just barge in on her apartment one morning, carrying bagels and coffee (for increased audacity, the American version of the movie has him showing up while she's still in bed with her girlfriend.) Having been completely blindsided, and confronted with the fact that one of the victims of her hacking knew that she'd hacked him, she agrees to work with him. Surprisingly, the two of them end up hitting it off.
During Murderess’ Rescue Arc, Lu, stuck in the Dark Ones’ tunnels with little hope of escape, after Hallwad charged at the Dark Onesin blind fury for torture his sister Aucasis, sits on their royal throne in the main hall, tells them exactly who she is, and outright lies to them that she came to renew the Killer’s ancient pact with them. They don’t buy it, but it gives her enough time to rescue both Hallwad and Aucasis.
Kelsier in Mistborn: The Original Trilogy used to be the most famous theif in the Final Empire. Once his wife was murdered by the Lord Ruler, he set his sights a bit higher, contracting with the rebellion to steal the Final Empire's capital and sell it to them. And even that is small-scale compared to his real plan: start a new religion around himself, die, return from the dead (which he'd already done once), and thus trigger a mass rebellion against the Lord Ruler.
In the Worldwar series, Otto Skorzeny lives for this trope (one could say the same about the historical Skorzeny, for that matter). At one point, he smuggles several kilos of ginger across the battle lines, looking to buy one of the Lizards' targeting systems, invoking this trope when he sets out; he manages to drive an entire tank out of the depot without being stopped, because no one ever imagined anyone who wasn't a Lizard driving one of their vehicles.
Horatio Hornblower: In Atropos, Hornblower scares away the much bigger and better-armed Castilla by sailing towards it while signaling to a non-existent British squadron for backup. And it works.
In A Wolf In The Soul, after Greg breaks another student's arm, Aram helps him escape campus police by giving him a ridiculously conspicuous hat. After all, the police will be looking for someone skulking around trying to hide, not somebody walking proudly down the street wearing garish clothes.
A somewhat understated version is found in Jodi Picoult's novel Perfect Match. After a priest is accused of molesting the protagonist's five-year-old son, she walks into the middle of the courtroom and shoots him in the head four times. Afterwards, she pleads insanity, her defense essentially being "I'd have to be crazy to kill someone in a courtroom."
In The Fault in Our Stars, Gus' speech to Monica's mom after she catches him, Hazel, and Isaac egging Monica's car, which actually succeeds in getting her to leave them alone to finish their vandalism.
Gus: Ma'am, your daughter's car has just been deservedly egged by a blind man. Please close the door and go back inside or we'll be forced to call the police.
In the urban fantasy Red Room series, Talbot decides the best way to sneak past the advanced sensors of an enemy is to use a magic carpet. He wants to play Steppenwolf's song about such while doing so. Made Doubly-Funny as the book had been largely serious until this.
Solo Command: The entire "Millennium Falsehood" ploy. Basically, using a fake Millennium Falcon, the squad makes it appear that General Solo is pulling these sorts of stunts, personally flying in to Warlord Zsinj's worlds to rally the population to the New Republic.
Mercy Kill: The main plot involves hunting for a treasonous general who has come into possession of a technique that will completely change his identity, to the extent that not even biometrics or DNA testing could reveal his old self. The only downside is that it takes several months to perform in full. At the climax of the book, running low on other options, team leader Piggy banks everything on the belief that the general has already gone through the procedure and is using a disguise to "pretend" to be his old self, ending in the general being arrested for (among other things) his own murder!
Tinker, Tailor, Soldier, Spy: One of George Smiley's accomplices is sneaking about in a part of Headquarters that he shouldn't really be in. He comes across a door which slams closed on a spring, and remembers Smiley saying "If you have to make a noise, make a loud one." So our man lets the door slam really hard, as if he had every right to be there. No one investigates.