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{{Smug Snake}}s in {{Literature}}.
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* ''{{Literature/Airframe}}'': Bob Richman, who comes from the family that founded the aircraft company the book centers around. Despite that, he holds no loyalty to it, or them, and turns out [[spoiler: to be in on a plan to allow John Marcer to cut a deal that will put him in charge of the entire company by arranging for Casey Singleton to take the fall]].
* ''Literature/AngelaNicely'': Tiffany is a very arrogant girl who thinks she’s the best at everything. For instance, in “Cupcake Wars!”, she’s confident that her cupcakes will be the most popular.
* Tom in K.A Applegate's ''Literature/{{Animorphs}}'', or rather the second Yeerk that controls him. [[TheLancer Marco]] can approach being a heroic version at times and [[spoiler:David]] spends the third arc of his trilogy as one. Fittingly, all three of these characters are seen actually morphing into snakes. [[SarcasmMode Not too subtle, K.A.]]
* Vidal Vordarian from Creator/LoisMcMasterBujold's novel ''Literature/{{Barrayar}}''. He wants to run Barrayar but is effortlessly and ''unintentionally'' defeated in his attempt to do it legitimately by Aral Vorkosigan. So he tries a coup but fails to capture the true heir or assassinate the Regent. He gets the ruling council to go along, but only at obvious gunpoint. And then he [[spoiler:loses his head to [[MamaBear Vorkosigan's wife]].]] His "greatest" achievement is his implied rape of the dowager Empress, who he marries (again, obviously by force). Smug Snake indeed.
** He doesn't actually marry her. He just announces their engagement.
* Simon Lovelace from ''Literature/TheBartimaeusTrilogy'' is a perfect example, though he was smarter than the average Snake.
** John Mandrake also counts. Actually, most of the wizards do.
*** As does Bartimaeus himself. Sure, he is not stupid or inept, but no amount of intelligence or power can match the size of his ego!
* ''Literature/BazilBroketail'': Thrembode is far too full of himself and far too much convinced of his own ingenuity for his own good.
* In ''Literature/TheCaineMutiny'', Lt Thomas Keefer definitely qualifies, as does attorney Barney Greenwald to some extent.
* There's a lot of [[TheChessmaster Chessmasters]] and [[MagnificentBastard Magnificent Bastards]] in ''Literature/CodexAlera'', so there's also a good few people who only ''think'' they're such. There's Sarl, who tried to ally with a HordeOfAlienLocusts to take over his homeland (his next appearance sees him running away with a refugee fleet), Senator Arnos, who while tactically decent has failed to realize that his patron Invidia sees him as a pawn who's useful [[YouHaveOutlivedYourUsefulness at the moment]], and Kalerus Brencis Minorus, who while very powerful is also basically a schoolyard bully who has a WellDoneSonGuy complex to his AxCrazy father.
* The title character of ''Literature/ACoffinForDimitrios'' is a good fit, being a clever schemer, but such an unpleasant treacherous thug that he's completely unlikable. Also notable is that he ends up addicted to the same drugs he sells, something which would never happen to a MagnificentBastard. Interestingly, the character might have been an inspiration for Keyser Soze of ''Film/TheUsualSuspects'', who by contrast is definitely a MagnificentBastard.
* Two villains from the Literature/ForgottenRealms trilogy ''Literature/CounselorsAndKings'' stand out. Lord Procopio Septus is a canny and ambitious politician, but he's shortsighted and very proud, which make it possible for him to be OutGambitted comparatively easily if you know what you're doing. [[spoiler: Dhamari Exchelsor]], though he puts on a friendly facade, is a treacherous and venal little man often compared to a weasel or ferret both in terms of appearance and demeanor. He's sneaky, but he's too petty to have a real MagnificentBastard's grasp of the big picture.
** Ironically [[spoiler:Dhamari]] did at one point ''artificially'' turn himself into something approaching a MagnificentBastard- upon capturing an amulet enspelled to protect its wearer from him, he wore it himself and was protected ''from himself'', causing him to become much more cunning, manipulative, and successful. Once he lost it, though, it was a quick trip back to Smug Snake-hood.
* Uriah Heep in Dickens' ''Literature/DavidCopperfield'' is one of literature's most notable smug villains; he has the ability to make the term of address "Master Copperfield" seem insincere, and is always wittering on about how "humble" he is. [[spoiler: Naturally, he's planning to swindle everything away from the other characters.]]
* ''Literature/InDeath'': Some of the murderers are definitely this. A notable example is Dr. Waverly in ''Conspiracy In Death''. He is so arrogant and has such a God complex that he simply assumes one of his security droids will handle Roarke easily. He clearly doesn't know Roarke at all. He happily gives the names of the people he's been working with to Eve while he's got a hostage. He had been conducting experiments on regenerating human organs, using sidewalk sleepers and poor people as guinea pigs, and the experimentation resulted in their deaths. He flies into a pompous speech about how his serum can be used on any organ and eventually will be used on bone, muscle, and tissue, which will eventually result in perfect human beings. Oh, and he'll get to decide who will be part of the survival of the fittest, and he boasts that the world will be a better place without the dregs that weigh it down. However, when Eve turns the tables on him, he gets scared and begs for his life. Yep, he thought he was so great and smart...but he wasn't.
** In general, as soon as a bad guy says something about how they're going to take down or hurt Roarke easily, you know s/he will be put in this category. The DirtyCop Jerry Vernon from ''Judgment In Death'' is a good example. He gets in Eve's face about the fact that she is looking for dirt on him, and he brags about how he is going to sue her and bleed that rich husband of hers. No one bleeds Roarke. If s/he tried, he would squish that person like the bug s/he is.
* Literature/{{Discworld}}:
** Cosmo Lavish from the novel ''Literature/MakingMoney'' is an [[LoonyFan obsessed fan-boy]] of Vetinari, who is an actual MagnificentBastard. He tries extremely hard to be just like Vetinari, trying to get his old clothes and practising his [[CharacterTics eyebrow-raising]]. [[spoiler: He eventually goes crazy, thinking he [[NapoleonDelusion really is Vetinari]], and gets committed to an insane asylum, which apparently has a whole ward dedicated to people who think they're Vetinari.]] His sister, Pucci Lavish, isn't much better.
** Lord Hong from ''Literature/InterestingTimes'' is another, though less funny and less pitiful, example. He is, admittedly, AwesomeByAnalysis and the BigBad of the novel, so not a pure specimen. He does, however, exhibit the trademark snarky attitude, overconfidence, and pre-failure breakdown.
** There's also the Supreme Grand Master, a.k.a. [[spoiler:Lupine Wonse]] from ''Literature/GuardsGuards'', who vastly overestimates his own power in summoning and controlling the dragon which terrorizes Ankh-Morpork, in that he can summon it but has no means to control it.
** [[spoiler:Dragon King of Arms]] from ''Literature/FeetOfClay'', the mastermind behind the plot to poison Vetinari and replace him with a puppet ruler. His plan falls apart because he arrogantly underestimates Vimes and the rest of the City Watch.
* In ''Literature/DoctrineOfLabyrinths'', Robert of Hermione isn't the most formidable villain the series has to offer, but he's arguably the most obnoxious. He's a scheming, pompous [[AristocratsAreEvil aristocrat]] with all the ambition and malevolence of a BigBad, but he's hampered by his lack of foresight and a tendency to vastly over-estimate his own [[SmallNameBigEgo cunning and importance]].
* In the ''Literature/{{Dragonlance}}'' novels, Quarath, the EvilChancellor to the leader of the CorruptChurch fits this model. His own ambitions for power and wealth are compared to the epic confrontation between ''actual'' {{Magnificent Bastard}}s Raistlin and Fistandantilus of which Quarath is completely unaware. Ended up [[spoiler: being squashed by a pillar as his temple collapsed]] when his master pisses off the gods that Quarath had stopped believing in by this point.
** In the later War of Souls trilogy we get Morham Targonee, [[NamesToRunAwayFromReallyFast Lord of the Night]], who despite his impressively evil-sounding title is a scheming accountant who happened to be in the right place at the right time to seize power. When the local DarkMessiah shows up and steals his job, she punishes him in what is perhaps the worst way a Smug Snake can experience- by forcing him to realize his own cosmic insignificance before killing him.
* Madrigal Raith from ''Literature/TheDresdenFiles'' is nowhere near the MagnificentBastard he thinks he is. He persists in thinking of Harry as DumbMuscle, and torpedoes his own plan by ''trying'' to pull off an XanatosGambit via sending Harry after his competitor, which results in Harry digging deep enough to discover Madrigal too.
** ''Literature/TheDresdenFiles'' has a lot of these, but bonus points go to Quintus "Snakeboy" Cassius, a Denarian who is not only a clear-cut example of the trope but a ''[[ScaledUp literal]]'' example as well.
* Dr Bill Tanner from [[Literature/AlexRider Snakehead]] is a disgusting scumbag who tries [[spoiler:to sell Alex's organs on the black market]]. He's so smug he brags about how Alex can't escape, which helps him break out. He's so unlikeable when [[spoiler: he kills himself, the audience feels no sympathy.]]
* Cugel the Clever, of Creator/JackVance's ''Literature/DyingEarth'' books, while he lives on the border between this and being an actual MagnificentBastard, usually leans towards the Smug Snake side, being a complete sociopath, and nowhere near as clever as he imagines himself. ''And he's the protagonist, folks''.
* Duke Telrii from ''Literature/{{Elantris}}'' is an example of the "thinks he's a MagnificentBastard" type, though he winds up little more than a pawn of the book's real MagnificentBastard, [[VillainProtagonist Hrathen]]. King Iadon from the same book is also an example- he turns out to be a lot smarter than Telrii ([[ObfuscatingStupidity and a lot smarter than he lets on]]), but his vision is simply too narrow to let him accomplish anything of real significance, and his [[PoliticallyIncorrectVillain misogyny]] stops him from realizing Sarene is a threat to him until too late.
* ''Literature/TheElderEmpire'': Naberius Clayborn has managed to put himself in a position where he'll be the next Emperor of the world and is ''very'' smug about it. However, as the book wears on, the "smug" part fades in favor of the "snake" part, as he starts betraying people left and right. [[spoiler:[[EldritchAbomination Nakothi's heart]] corrupting him certainly didn't help, but nobody really liked him even before that]].
* [[SinisterMinister Primate Annias]] in ''Literature/TheElenium'' definitely qualifies. One of the most spectacular examples of this was an attempt to frame the protagonist's fellow knights for a blasphemous massacre. Unfortunately for the plan, the Pandion Knights found out about the impending massacre first and warned the prospective victims, even turning the massacre back on the would-be murderers. And unfortunately for Annias, he was relying on the massacre to take place and giving fake evidence of the Pandions' involvement before the Pandions could respond to the event. This doesn't work well for him, as it becomes very obvious to everyone involved that the crime never took place when the 'murdered' duke comes forward to give evidence of what really happened.
** This event, however, becomes evidence that, at least for this situation, Annias's SmugSnake qualities were slightly subverted. Sparhawk notices that, while Annias can be clumsy, he wouldn't have been that clumsy, revealing that he was NotHimself, but acting more like how a [[MageSpecies Styric]] would act if they were trying to deceive someone, tipping the Pandions off to Annias's [[GodOfEvil associates.]]
* In ''Literature/TheEnormousCrocodile'', the titular VillainProtagonist schemes to eat children by disguising himself as a coconut tree, a see-saw, a carousel statue and a lunch-bench. While certainly ''cunning'', he is not nearly as ''clever'' as he thinks he is and shoots himself in the foot by gloating about his intention to eat children in front of four other animals in the jungle. [[NiceJobFixingItVillain This is what allows them to foil his plans.]]
* Depending on who you ask, Senna of Literature/{{Everworld}} is either one of these or a MagnificentBastard. Her mother is a straight example.
* Prince Regal in Creator/RobinHobb's ''Literature/{{Farseer}}'' trilogy. A spoiled, petty, selfish youngest prince, he is obsessed with ruling and having power while being completely incompetent as a ruler.
* In ''Literature/ForeverAndADeath'' Richard Curtis is a very self-satisfied man, and he does have a grand, ruthless plan and vast business empire, but the worst Bond villain, on his worst day, would still be a bigger threat than him, given his tendency for stupid decisions.
* Zil Sperry from ''Literature/{{Gone}}'', a [[UsefulNotes/AdolfHitler Hitler]] expy whose plans are mostly either nuisances, with their only major negative effects being unintentional, or things he's tricked into doing by [[BigBad Caine]], yet he thinks he's leading a major, important movement.
* The Shadow Spirit from the ''Literature/{{Goosebumps}}'' book ''Literature/TheGhostNextDoor'' is this ''in spades''. They are so sure that [[spoiler:Danny will die in the fire he started as a prank that [[GoneHorriblyWrong Went Horribly Wrong]]]], that they [[DidntThinkThisThrough don't consider the idea]] that [[spoiler:since Hannah is a ghost, she can just walk right through them to save Danny]].
* ''Literature/HarryPotter''
** [[Characters/HarryPotter Dolores Jane Umbridge]] in ''Literature/HarryPotterAndTheOrderOfThePhoenix'' is a purposeful Smug Snake. A sugary sweet StepfordSmiler who is [[FantasticRacism biased against non- and half-humans]] and [[ObstructiveBureaucrat uses laws and technicalities]] to get her way, Umbridge is one COLOSSAL bitch, who tortures children during detention.
** Draco Malfoy. [[spoiler: In his Sixth Year he goes through a BreakTheHaughty situation, that leaves him a wreck of a person. The Epilogue hints that he became better after the whole ordeal.]]
** Draco's dad Lucius is one too (apparently being a Smug Snake runs in the family). He's very smart and has the polish of a MagnificentBastard, but his arrogance and certainty that [[VillainWithGoodPublicity he can get away with anything]] lead to some sloppy mistakes. By the end of the series, both Malfoys turn out weirdly pathetic after they are forcibly shown that an EvilOverlord does ''not'' a good houseguest make.
** Voldemort himself, with an emphasis on the "[[ReptilesAreAbhorrent Snake]]" part of Smug Snake. Voldemort has all the resources a MagnificentBastard could ever want, but his gigantic ego, which even influences [[spoiler: his choices of the Horcruxes containers ''and'' hideout]] leads him to making big mistakes.
*** The young Tom Riddle is shown to have been a much more smooth and successful schemer, largely because he knew how to keep a cool head and didn't yet [[ObviouslyEvil look like a monstrous snake-human hybrid]]. At any rate, whenever anyone talks about any version of Voldemort's genius, they're generally referring to his ''magical'' genius, which is unquestionable, rather than his ''tactical'' genius, which as has been mentioned above is a wee bit lacking.
** James Potter was supposedly this as a teenager. Problem was that he was genuinely talented and intelligent and actually pretty good (if not bigheaded at times). He grew out of it (even becoming [[ClassRepresentative Head Boy]] of Hogwarts in his final year).
** Severus Snape plays this straighter though was more subtle about it. This was occasionally seen in adulthood albeit more through his attitude on others.
*** Considering he and his enemy James were both very talented young wizards, this probably crossed over into ''SmugSuper.''
* ''Literature/TheHungerGames'': WordOfGod states Seneca Crane really has no idea what the true purpose of the games are or the ramifications of what occurs in them. He's just in it for the show biz.
* ''Literature/TheIdiot'' features Ferdyshchenko, who establishes himself as a thoroughly smug snake in one scene and doesn't do much else for the rest of the novel. At a party, Ferdyshchenko proposes a bizarre parlor game where all the participants confess the worst misdeed they ever committed. His confession was a story about stealing 25 rubles ([[ForTheEvulz for no reason whatsoever]]) from a house he was a guest at, then allowing a maid to take the blame for the theft, ultimately resulting in said maid being fired. From the way he tells his story, it's clear that he expects his listeners to be impressed with him--upon realizing that his story had exactly the opposite effect, he gets pissy and stays that way for most of the evening.
* ''Literature/{{It}}'': The eponymous monster is firmly convinced of its own superiority and views humans as nothing but mere toys and a food source. However, every time the Losers manage to get the upper hand against them, It flees. During the final showdown, in which It is grievously wounded and the Losers are bearing down on It, It considers the possibility that It is NotSoInvincibleAfterAll.
* Steggles from the ''Literature/JeevesAndWooster'' series.
* Majority of the villains in ''Literature/JohnCarterOfMars'' (those who aren't are {{Worthy Opponent}}s that sooner or later befriend the heroes), but the Holy Therns and the First-Born are ''whole races'' of Smug Snakes. They consider themselves [[AGodAmI divine]] and [[FantasticRacism superior]] to everybody else in Barsoom, either because they were descendants to the {{Precursors}} or are closer to the local deity (The First-Born are particularly bad about it due to latter case). In reality, neither race is any more advanced than the supposedly savage Red Martians (the most civilized people on the planet), and are in fact, extremely dependent on Red slaves for nearly everything to maintain their society. When the main protagonist leads a massive assault against their strongholds, they fall extremely easily.
* ''Literature/MalazanBookOfTheFallen'': Clip doesn't treat anyone with respect, be it the brother of his supposed god or said god himself. He also seems unable to say anything without a superior smirk. He thinks his plan to take revenge upon his god by using said god's offspring is pure genius, never even considering that they may not be what they seem to his disdainful glance -- especially not his {{Unwitting Pawn}}s. Ultimately, he fashions himself a MagnificentBastard but ends up being a case of SmallNameBigEgo.
* Fulbert from the French novel ''{{Literature/Malevil}}''. He's an evil priest with a tiny, weak CorruptChurch and a ZeroPercentApprovalRating. The only reason he isn't overthrown is that he tricked everyone into giving him the food and weapons, [[OrcusOnHisThrone he sits in his fortified manor where nobody can touch him]].
* [[TheHeavy Mr Antler]] from the ''Literature/MediochreQSethSeries'' is an example. He's almost unbearably smug, even though he actually gets successfully duped or manipulated not only by the heroes but by ''most of the other villains''. Including ''[[DumbMuscle Maelstrom]]''.
* Several characters in ''Literature/TheMentalState'' are fairly self-confident, but the one that really stands out is the BigBad, Saif Dhu Hadin. He is so full of himself; he even has a nametag that reads ‘[[Film/TheUsualSuspects K. Söze]]’. Being a psychopath, his inflated ego comes equipped with a talent for manipulation and a devious mind. He also has an IQ of over 140 and is particularly good at assuming complete control over other people's lives. Fortunately, [[SociopathicHero Zack]] is better.
** Commissioner Viceman is also fairly smug about his position and abilities. He enjoys having the moral high-ground and believes his ultra-conservative views to be infallible. He even recruits an undercover officer to infiltrate a prison and spy on the inmates. This ultimately proves to be his undoing when [[spoiler:Zack finds out and blackmails him]].
* Literature/TheMillenniumTrilogy has loads of people who fit this, though each book has a standout:
** From ''The Girl With The Dragon Tattoo'', Nils Bjurman thinks he's being extremely clever by using his control over a mentally incompetent girl's money to coerce her into submitting to his fondness for sadistic rape and torture, especially since he thinks it unlikely her word would be believed over his if she tried to report him. However, the book explicitly makes it clear that he makes no effort to cover the physical evidence he leaves on and in her, and that if she did go to the police, mentally incompetent or not, he would be finished immediately. Also, even ignoring this mistake (and the more serious one of the girl in question being [[DarkActionGirl Lisbeth]] [[GuileHero Salander]],) [[RapeIsASpecialKindOfEvil his crimes are so heinous]] that there is no way he could ever incite any reaction beyond absolute disgust and contempt from the reader.
** From ''The Girl Who Played With Fire'', [[spoiler: Alexander Zalachenko, Lisbeth's father]], clearly thinks he's a MagnificentBastard but falls very squarely into this trope. Even though he was a competent spy for the Soviets, his arrogance and lack of self-control led him to balls up an assignment so badly that he needed to defect to save his own skin. After defecting to Sweden, he frequently got drunk, abused his girlfriend so badly she had permanent brain damage and delighted in making his handlers bail him out of his self-inflicted trouble. Following his eventual departure from the intelligence networks, he became a sex trafficker (a business which even TheDragon thinks is too high-risk for the mediocre profit it brings), essentially because he was a misogynist who enjoyed having power over women. When confronted, everything he says boils down to ScrewTheRulesIHaveConnections, and he continues to believe this, right up until [[spoiler: his handlers get fed up with him and blow his head off while telling him just how much contempt they have for him]].
** From ''The Girl Who Kicked The Hornets' Nest'', Dr Peter Teleborian spends the book confident that his (falsified) assessment of [[spoiler: Lisbeth Salander]] will be accepted without question, and is so used to being respected and admired that it genuinely throws him when someone does not fall for his charm and nod in agreement with everything he says. He has such faith that his [[ScrewTheRulesIHaveConnections connections]] will keep everything under wraps that he doesn't even do a good job of covering his tracks, and when his connections are compromised, the glaring errors become clear to everyone. However, his main flaw is that he has come to believe his own lies, and consequently completely underestimates his former patient. Also, he is a sadistic pedophile, so would be disqualified from {{Magnificent Bastard}}-dom even if he hadn't screwed everything up.
*** In terms of competence, the Section qualify, as they spend virtually the entire book being OutGambitted to the point of EpicFail by Salander's friends while believing they have the upper hand. Also, as Cold War veterans, they are unsuited to the 2000s, and they seem unable to understand that you can no longer expect everyone in the country to tolerate your crimes simply because they were committed in the interests of "National Security", and when a younger man tries to get them to realise that times have changed, they dismiss him as lacking the spine needed to do his job.
* Lord Straff Venture of ''Literature/{{Mistborn}}'' is a comparatively competent Smug Snake, being a skilled long-range {{Chessmaster}} and the most powerful nobleman in TheEmpire apart from its PhysicalGod leader. At the same time, though, his arrogance, lack of skill in immediate, detailed manipulations, and the numerous petty and vile traits he shows in his interpersonal relationships keep him out of full MagnificentBastard range.
* Imogen Herondale from ''Literature/TheMortalInstruments''. A [[FantasticRacism racist]] EvilChancellor and ManipulativeBitch with a pathological hatred of children. She thinks she's playing everyone throughout ''City of Ashes'' but her grand plan fails spectacularly and Valentine Morgenstern viciously humiliates her, resulting in her breakdown. Unusually for this trope, she is revealed to have a sympathetic side and [[spoiler:ultimately redeems herself by [[RedemptionEqualsDeath sacrificing her life to save Jace]]]].
* Philonecron from ''The Cronus Chronicles''. He considers himself an evil genius, and treats everyone he meets like dirt, but is defeated by two middle-school kids.
* Mr. Collins in ''Literature/PrideAndPrejudice'', whilst not exactly a villain, is rather smug and slimy, with a rather vast (and largely unearned) self-regard that makes him believe that Elizabeth Bennet is rejecting his marriage proposal out of some feminine desire to string him along when she's rather explicitly stating that no, it's because she ''doesn't like him''.
* Vizzini from ''Literature/ThePrincessBride''. Although he certainly is clever and recognizes his weaknesses, he has a colossal ego and treats everyone, even his own henchmen, like dirt. His arrogance also prevents him from recognizing that The Man in Black would never pull his battle of wits unless he knew he would win, and that there was no sure way of guessing which cup had the poison. There's a reason he's the former TropeNamer for OutGambitted.
* Frederick Chilton from ''Literature/RedDragon'' and ''Literature/TheSilenceOfTheLambs'', who comes across as a bully as head of the Chesapeake State Hospital for the Criminally Insane. In ''Silence'' he makes the key mistake of handing Hannibal Lecter over to people who don't understand how dangerous he can be, which gives Hannibal the opportunity to escape.
** Paul Krendler of the same series definitely qualifies, though it only becomes noticeable in ''Hannibal''. In many ways, he's far more of a Smug Snake than Chilton was on his worst day. Like Chilton, he gets his comeuppance at the hands of Lecter.
* ''Literature/RomanceOfTheThreeKingdoms'': Dong Zhuo and Lu Bu are obvious ones, and Cao Cao has shades of it when he's opposing the nominal protagonist, but even Liu Bei has his moments of snake-ness in the eyes of a modern audience. (But that WhatTheHellHero reaction is probably intentional, as the author was suffering from ExecutiveMeddling.)
** Yuan Shu is probably the biggest example of the book. He declares himself the emperor with only the Imperial Seal to back up his claim, and thus alienates everybody. And his petty villainy while a member of the Coalition against Dong Zhuo, withholding food from ally Sun Jian's army to keep Sun from gaining too much glory.
* Since the Yamiko of ''Literature/SailorNothing'' are the personification of their host's id, it's easier to list the ones that don't fall into Smug Snake, namely Argon, [[PragmaticVillainy Cobalt]], and Ohta, Cobalt's right-hand man. Dark General Radon is a particularly vile example of {{Smug Snake}}ery, being an arrogant KnightTemplar and EvilMentor before his FaceHeelTurn; afterwards, he just gets worse.
* Yanagisawa in the ''Literature/SanoIchiro'' mysteries, so much.
* Count Olaf of ''Literature/ASeriesOfUnfortunateEvents'' is a ''huge'' one. He has some pretty {{Paper Thin Disguise}}s (to the Baudelaires, at least) and he constantly remarks about how evil and cunning he is. Also, he suffers from plot-relevant VillainDecay and he clearly lacks common sense (seeing as he asks the Baudelaires to buy some roast beef with their fortune when he knows they're not eligible yet).
* Gustav Fiers, aka The Gentleman from the ''Literature/SpiderManSinisterSixTrilogy''. He certainly ''thinks'' he's a MagnificentBastard, and looks and acts the part, being an excellent ManipulativeBastard and {{Chessmaster}}, and ManOfWealthAndTaste who successfully manipulates the whole of the Sinister Six, has evaded law enforcement for years, and refers to himself as an "investor in chaos". Yet he fails to earn the audience's respect due to his contemptuous attitude and his unpleasant personality, utter heinousness (only his genuine affection for his equally monstrous brother, [[TerroristWithoutACause Karl]], keeps him from being a total monster), and underestimation of Spider-Man, The Chameleon, and Dr. Octopus put him squarely in this trope.
* In ''Literature/SkulduggeryPleasant'', Davina Marr is a patronising, ageist, sadistic StepfordSmiler [[OhCrap who makes Dolores Umbridge look like Mother Teresa]]. Whenever she appears, you want to climb inside the book and punch her in the face. Nevertheless, she's an unwitting pawn in someone else's diabolical plan, spends most of book 5 unconscious, and is unceremoniously killed while tied up and begging for her life.
* Queen Cersei Lannister in ''Literature/ASongOfIceAndFire''. Overestimation of her own cleverness is one of her main character traits. There's a prophecy that everything that could possibly go wrong in her life will, so her ruthless methods are understandable, yet her incompetent attempts at manipulation and power-grabbing alienate almost every one of her allies and [[SelfFulfillingProphecy could well lead her to the terrible fate predicted in the prophecy]].
** Really this could be the hat of the entire Lannister house, even the more clever members of the family who qualify as [[TheChessmaster Chessmasters]] in their own right are still so odious and preening it's hard to root for them. [[spoiler:[[CharacterizationDevelopment Jaime gets better]], and Tyrion for all his faults seems more like an AntiVillain.]]
*** Or at least the main branch. Tywin's brother Kevan comes across as a decent and obedient man, while his oldest son Lancel is a rather foolish and weak-willed figure easily manipulated by his more intelligent cousins.
** Lord Petyr "Littlefinger" Baelish ''seems'' like a Smug Snake to most of the other characters, [[spoiler:but this is a smokescreen to hide what is actually a subtle MagnificentBastard, who has apparently single-handedly organized the War of Five Kings as well as the assassination of two kings, while simultaneously organizing the rise of a new queen... his protegee Sansa Stark.]]
*** [[spoiler:Later it's subverted back again by revealing that [[SpannerInTheWorks his lackeys are imprisoned and that there are more Starks alive than thought]].]]
*** The trope is also subverted [[spoiler:by the eunuch Varys, who wears his SissyVillain persona as a mask to operate behind the collective back of the DecadentCourt.]]
** In every appearance of Viserys, the book contrasts his attitude ("You don't want to wake the dragon, ''do you?''") with the reality: he's a spineless, pathetic little man who bullies his sister Daenerys because there's nobody else even close to being weak enough to let him get away with it. [[spoiler:When Dany develops enough strength to resist him, Viserys mentally collapses and gets himself killed within a few pages.]]
** Theon Greyjoy could be the poster boy for this trope. [[spoiler:At least until A Dance with Dragons, where Ramsay Bolton has tortured him into insanity - he's a thoroughly broken shell whose mind slides between his current identity as 'Reek', Ramsay's completely subservient and terrified slave, and his former identity, Theon, who bears little to no resemblance to his former self.]]
** House Frey consists of so many Smug Snakes it could easily be considered their hat. There are a few exceptions to the norm within their family, but they all fade out of prominence as the more evil members take charge.
** The Ironborn can also count as this, as they have a smug sense of superiority to the "greenlanders", those that live on the mainland. They constantly look down on those that talk about relatively normal values, while the Ironborn believe in a MightMakesRight philosophy. Despite these feelings, they have never won a significant victory over the rest of Westeros except back when they were a full kingdom and had the entirety of the Riverlands under their control. What makes it even worse is that they join the War of the Five Kings because Balon wants to "take what is his", despite the fact that he had already been beaten once before, easily, by the Iron Throne. The Ironborns' only successes are because they're attacking places that are lightly defended in the middle of a civil war.
** There's also the Wildlings, who live beyond the Wall. They believe themselves superior to the "kneelers" of the South because they bend the knee to kings, while the Wildlings believe that MightMakesRight, and that they also take what is theirs. They even hold this attitude despite the south having better weapons, more people, better horses, armor, and that every time they've managed to get past the wall they're swiftly defeated and sent packing.
* ''Literature/TheTravelersGate'': Talos, one of the Damascan Heirs, believes that he is a genius plotter and master swordsman. He is not. He's not a ''terrible'' plotter, but his father sees a lot more than he thinks, and he keeps allying with the wrong people. He is, however, a terrible swordsman; Simon spends a good chunk of their duel assuming that Talos is playing with him before realizing he's really just that bad.
* ''Literature/TowerOfSomnus'': Anna Donnst thinks she is much, much more competent than she actually is, and lashes out whenever anyone proves better than her, even by accident. [[spoiler:According to her mother, it took massive bribes to keep her grades at a reasonable level; despite all her advantages, Anna would have been headed for factory work otherwise]].
* In ''Literature/TwilightSparkleAndTheCrystalHeartSpell'', Trixie and Gilda supply their normal arrogance, but manage to achieve very little.
* [[LizardFolk Cree Bega]], TheDragon in ''Literature/TheVoyageOfTheJerleShannara'' is slipperily obsequious and has a penchant for ColdBloodedTorture and murder, BreakTheCutie, and [[KickTheDog Kicking]] TheWoobie. He's also ungodly arrogant, seeing all of the [[{{Snaketalk}} Little Peoplesss]] as [[FantasticRacism inferior beings]] worthy only of disdain. Even his undeniable bravery in combat and willingness to [[TheStarscream stand up]] to [[BadBoss The Isle Witch]] stems from this arrogance, and it ultimately gets him killed when one of {{the Woobie}}s [[TheDogBitesBack Bites Back]]. Utterly unlikeable, and truly disgusting. Stenmin, the EvilChancellor from ''[[Literature/TheSwordOfShannaraTrilogy The Sword Of Shannara]]'' is a more typical example, combining sliminess, DirtyCoward, and TheMole into one unloveable package.
* The emperor of France, UsefulNotes/NapoleonBonaparte, in ''Literature/WarAndPeace''. The characters take up at least a third of the book talking about, predicting the actions of, or plotting against him. When Prince Andrei and later when Balashov, an emissary of the Russian emperor, finally meet him, they're both struck by how disappointing he is compared to his reputation. [[AnAesop He's purposefully portrayed this way.]]
* Stopwatch of the Literature/WhateleyUniverse. Brilliant planner, head of The Masterminds, has managed to hide his best power from the SuperheroSchool Whateley Academy powers testing guys... and gets pwned by Phase in "Ayla and the Networks". He ends up having to beg Ayla for help and loses control of his own team of supervillains.
* Corlant of ''Literature/TheWitchlands'' thinks himself to be highly intelligent and a skilled Cursewitch who has every right to treat his boss' top agent like trash just because. Suffice to say, from the moment Iseult and Aeduen enter the stage, his supposed skills are looking less like brilliance and more like Corlant's an idiot who accidentally won the SuperpowerLottery.

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