Smug Snake/Literature

"It was his smug, oily certainty that infuriated her. Ray had mastered the art of speaking as if he were the only adult on the planet and everyone else was weak, stupid, or insolent. Under that brittle exterior, of course, was the narcissistic infant determined to have his own way. Neither aspect of his personality was particularly appealing."
 * Harry Potter
 * Dolores Jane Umbridge in Harry Potter and The Order of The Phoenix is a purposeful Smug Snake. A sugary sweet Stepford Smiler who is biased against non- and half-humans and uses laws and technicalities to get her way, Umbridge is one COLOSSAL bitch, who tourtures children during detention.
 * Draco Malfoy.
 * 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 Magnificent Bastard, but his arrogance and certainty that 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 a Complete Monster Evil Overlord does not a good houseguest make.
 * Voldemort himself, with an emphasis on the "Snake" part of Smug Snake. Voldemort has all the resources a Magnificent Bastard could ever want, but nooooooo... his circuitous plans fail utterly at basic logic, and while he is clearly trying for Magnificent Bastard he comes off as a third-rate Dastardly Whiplash.
 * Justified by the fact that his making so many horcruxes left him decidedly... unstable. 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 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 rather lacking.
 * James Potter was this as a teenager, though he supposedly grew out of it (even becoming Head Boy of Hogwarts in his final year).
 * Artemis Fowl from the book series of the same name is certainly a genius but his snarking is usually outdone by most of the other characters, he is physically weak and most of his plans fail due to him either having a crisis of conscience or due to his own overconfidence and incompetance. In short, for a criminal mastermind, this guy is overrated.
 * Minerva Paradizo from Artemis Fowl and the Lost Colony is trying to be a Magnificent Bitch and would be as she's easily as clever as Artemis and significantly more ruthless however she is obedient to her patronising and overprotective father, is easily outwitted by Artemis and suffers Villainous Breakdown when her own Dragon rebels against her.
 * In Skulduggery Pleasant, Davina Marr is a patronising, ageist, sadistic Stepford Smiler and Complete Monster 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.
 * Imogen Herondale from The Mortal Instruments. A racist Evil Chancellor and Manipulative Bitch with a pathological hatred of children. She thinks she's playing everyone throughout the book but her grand plan fails spectacularly and Big Bad Valentine Morgenstern viciously humiliates her, resulting in a Crowning Moment of Awesome when she breaks down. Unusually for this trope, she is revealed to have a sympathetic side and ultimately redeems herself by sacrificing her life to save Jace.
 * Queen Cersei Lannister in A Song of Ice and Fire. 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 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 Chessmasters in their own right are still so odious and preening it's hard to root for them. Lord Tywin's character in the TV series exemplifies this.
 * Lord Petyr "Littlefinger" Baelish seems like a Smug Snake to most of the other characters,
 * The trope is also subverted
 * 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.
 * Theon Greyjoy could be the poster boy for this trope.
 * In the Dragonlance novels, Quarath, the Evil Chancellor to the leader of the Corrupt Church fits this model. His own ambitions for power and wealth are compared to the epic confrontation between actual Magnificent Bastards Raistlin and Fistandantilus of which Quarath is completely unaware. Ended up  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, 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 Dark Messiah 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.
 * Cosmo Lavish from the Discworld novel Making Money is an obsessed fan-boy of Vetinari, who is an actual Magnificent Bastard. He tries extremely hard to be just like Vetinari, trying to get his old clothes and practising his eyebrow-raising.  His sister, Pucci Lavish, isn't much better.
 * Lord Hong from Interesting Times is another, though less funny and less pitiful, example. He is, admittedly, Awesome By Analysis and the Big Bad 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. from Guards! Guards!, 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.
 * The emperor of France, Napoleon Bonaparte, in War and Peace. 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. He's purposefully portrayed this way.
 * The title character of A Coffin for Dimitrios 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 Magnificent Bastard. Interestingly, the character might have been an inspiration for Keyser Soze of The Usual Suspects, who by contrast is definitely a Magnificent Bastard.
 * Vidal Vordarian from Lois McMaster Bujold's Vorkosigan Saga series. 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  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.
 * Frederick Chilton from Red Dragon and The Silence of the Lambs, 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.
 * Prince Regal in Robin Hobb's Farseer trilogy. A spoiled, petty, selfish youngest prince, he is obsessed with ruling and having power while being completely incompetent as a ruler. Like the example of Cersei above, he is much less clever than he thinks he is.
 * Uriah Heep in Dickens' David Copperfield 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.
 * Mr. Collins in Pride and Prejudice, 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.
 * Duke Telrii from Elantris is an example of the "thinks he's a Magnificent Bastard" type, though he winds up little more than a pawn of the book's real Magnificent Bastard, Hrathen. King Iadon from the same book is also an example- he turns out to be a lot smarter than Telrii (and a lot smarter than he lets on), but his vision is simply too narrow to let him accomplish anything of real significance.
 * Romance of the Three Kingdoms: 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 What the Hell Hero reaction is probably intentional, as the author was suffering from Executive Meddling.)
 * 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.
 * Cugel the Clever, of Jack Vance's Dying Earth books, while he lives on the border between this and being an actual Magnificent Bastard, 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.
 * The Dresden Files has a lot of these, a couple of whom (such as Lord Raith) are also Complete Monsters. Particularly Quintus "Snakeboy" Cassius, a Denarian who is not only a clear-cut example of those trope, but a literal example as well.
 * Simon Lovelace from The Bartimaeus Trilogy is a perfect example, though he was smarter than the average Snake.
 * John Mandrake also counts. Actually, most of the wizards do.
 * There's several in the Codex Alera, due to a high density of Chessmasters, Magnificent Bastards, and Complete Monsters. Particularly notable ones include the Evil Sorcerer Sarl, who tried to ; Senators Arnos, an Obstructive Bureaucrat who ordered a village slaughtered so he had an excuse to dismiss an honest officer who would balk at it; and Kalarus Brencis Minorus, who has a Well Done Son Guy complex to a Complete Monster.
 * Ray Scutter of Blind Lake.


 * Tom in Animorphs, or rather the second Yeerk that controls him. Marco can approach being a heroic version at times and spends the third arc of his trilogy as one.
 * Depending on who you ask, Senna of Everworld is either one of these or a Magnificent Bastard. Her mother is a straight example.
 * Cree Bega, The Dragon in The Voyage of the Jerle Shannara is a slipperily obsequious Complete Monster, with a penchant for Cold Blooded Torture and murder, Break the Cutie, and Kicking The Woobie. He's also ungodly arrogant, seeing all of the Little Peoplesss as inferior beings worthy only of disdain. Even his undeniable bravery in combat and willingness to stand up to The Isle Witch stems from this arrogance, and it ultimately gets him killed when one of the Woobies Bites Back. Utterly unlikeable, and truly disgusting. Stenmin, the Evil Chancellor from The Sword Of Shannara is a more typical example, combining sliminess, Dirty Coward, and The Mole into one unloveable package.
 * Lord Straff Venture of Mistborn is a comparatively competent Smug Snake, being a skilled long-range Chessmaster and the most powerful nobleman in The Empire apart from its Physical God 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 Magnificent Bastard range.
 * Vizzini from The Princess Bride. 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 Trope Namer for Out Gambitted.
 * Two villains from the Forgotten Realms trilogy Counselors and Kings 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 Out Gambitted comparatively easily if you know what you're doing., 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 Magnificent Bastard's grasp of the big picture.
 * Ironically did at one point artificially turn himself into something approaching a Magnificent Bastard- upon capturing an amulet enspelled to protect it's 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.
 * Fulbert from the French novel Malevil. He's an evil priest with a tiny, weak Corrupt Church and a Zero Percent Approval Rating. The only reason he isn't overthrown is because he tricked everyone into giving him the food and weapons, he sits in his fortified manor where nobody can touch him.
 * Gustav Fiers, aka The Gentleman from the Spider-Man novelisations, The Sinister Six Trilogy. He certainly thinks he's a Magnificent Bastard, and looks and acts the part, being an excellent Manipulative Bastard and Chessmaster, and Man of Wealth and Taste 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, Karl, keeps him off the Complete Monster list), and underestimation of Spider-Man, The Chameleon, and Dr. Octopus put him squarely in this trope.
 * Count Olaf of A Series of Unfortunate Events is a huge one. He has some pretty Paper Thin Disguises (to the Baudelaires, at least) and he constantly remarks about how evil and cunning he is. Also, he suffers from plot-relevant Villain Decay 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).
 * 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.
 * In Death: 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 with a serum. He used sidewalk sleepers and poor people as guinea pigs, and the experimentation resulted in their deaths. He flies into a pompous speech about how this 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 Dirty Cop 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.
 * The Idiot 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 (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.
 * Zil Sperry from Gone, a Hitler expy whose plans are mostly either nuisances, with their only major negative effects being unintentional, or things he's tricked into doing by Caine, yet he thinks he's leading a major, important movement.
 * Yanagisawa in the Sano Ichiro mysteries, so much.
 * Steggles from the Jeeves and Wooster series.
 * Since the Yamiko of Sailor Nothing are the personification of their host's id, it's easier to list the ones that don't fall into Smug Snake, namely Genre Savvy Argon, Pragmatic Villain Cobalt, and Ohta, Cobalt's right-hand man. Dark General Radon is a particularly vile example of Smug Snakeery, being an arrogant Knight Templar and Evil Mentor before his Face Heel Turn; afterwards he just gets worse.
 * Stopwatch of the Whateley Universe. Brilliant planner, head of The Masterminds, has managed to hide his best power from the Super Hero School 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.