Who hasn’t found themselves entranced by a charming villain? Unfortunately, it seems we’re especially hooked when that charming front comes with a nasty dangerous streak that switches on without a moment’s warning. Here are ten villains who really bring the charm, whether it be through their silver-tongued speech, dashing looks and keen sense of fashion, or their witty, intelligent, and cunning personality, and also to whom betrayal is second nature.
Screwtape from The Screwtape Letters by C. S. Lewis: Screwtape doesn’t conceal the fact that he is a demon doing his utmost to keep people away from “The Enemy” (God) and lead them to sin, misery, and eventually to live with “Our Father Below.” But he shows great intelligence, cunning, and insight in his suave manner of expressing his thoughts to his less competent nephew, Wormwood, and it’s a little disturbing how easily we can sympathize with and appreciate his point of view. Even knowing how twisted and perverse his agenda is, it’s hard to not be impressed by his keen understanding of human weakness and his success as a demon.
Iago from Othello by Shakespeare: It’s almost impossible to look at Iago’s track record without recoiling in horror. This iconic Shakespearean villain has absolutely no qualms about lying, betrayal, and murder, and even after he is eventually caught, he refuses to explain the motivation for his wild, unreasonable hate. However, he is also terribly good at persuading people that he is their friend and is looking out for their best interests when he’s secretly plotting their downfall. Even in his soliloquies, it’s hard to tell if he is sharing his sincere feelings or just stringing us along with more lies and pretension.
The Sphinx from Fablehaven by Brandon Mull: I loved this character as soon as I first encountered him. A wise, ancient human-like but perhaps-not-human being who is completely at ease in the magical world and inspires awe, fear, admiration, and suspicion from all sides? MORE PLEASE. I love how the Sphinx is so mysterious (hence his name) that it’s virtually impossible to tell if he’s a good character or a bad character. He makes you want to trust and believe him completely, but that could be just because he’s such a good liar. He knows how to read people; he’s patient but always thinking and planning to stay a step ahead of foes; and he doesn’t joke around or make stupid mistakes the way some villains do. He’s smart, likable, and a total charmer who comes across as wanting to be your instant best friend, but you also get the sense that he is ruthless and will take any measures to keep his secrets safe.
Moriarty from Sherlock: Confession: To be entirely honest, most of my assessment of this character comes from the BBC Sherlock TV show, since I haven’t read Arthur Conan Doyle in years. Moriarty is the dark and evil foil for Sherlock Holmes–he has the intelligence and the skills to be the mastermind of pulling off illegal heists and crimes, but he is detached from and bored with the world’s obsession with these petty games and power struggles. Like Holmes he uses crime as an escape from the dull, irrational real world and as a way to exercise his mind and to compete with the minds of others. And he has a lot of the same appeal as a character as Holmes. He’s intriguing, mysterious, unpredictable, and can be smooth, pleasant, and charming (even more so than Holmes, really, because he uses various personae to manipulate and toy with other people’s feelings). He jeers at Holmes for trying to fit into the good, safe, boring ideology of society and not giving into his darker, chaotic side, where his genius would be free of moral constraints and could achieve far greater accomplishments (according to Moriarty). And even though we know he is so, so wrong and that he’s a despicable, awful, cruel person, we can’t help but be fascinated by his brilliance and maybe want to see Holmes channel a little bit of that.
Magneto from X-Men: Apologies to comic-book fans: Aside from the odd YouTube viewing of the 1990s TV cartoon series, all my X-Men knowledge comes from the films. And from what the films tell me, Magneto is a foxy villain with a stone cold heart. He may seem like he’s working for the good of mutants everywhere and that he wants the right thing, but when it comes down to it, he’ll lie to, betray, and destroy anybody who gets in his way. No matter how often Professor Xavier (our champion white knight captain of the good mutants leader) tries to reach out to Magneto and to help him see how to use his abilities for the good of everyone, Magneto never goes along with Charles’s plans without having a back-up plan and an agenda of his own. His ridiculously awesome talent (controlling magnetic force fields, a.k.a. lifting cars, stopping or starting bullets, using any amount of metal in the vicinity to defeat basically anybody, etc.), his near-invincibility, and his charisma also make him pretty admirable and formidable as a villain. It’s easy to see why a bunch of mutants join with him – he flatters them and he’s kind of the king of the cool evil mutants.
Ferahgo from Salamandastron by Brian Jacques: The death of Ferahgo was the only death of a Redwall villain that I was truly heartbroken over. I was well aware of the clumsy faults that other Redwall villains possessed, such as vanity, stupidity, a misplaced confidence in their own abilities, etc., but Ferahgo stood out, in intelligence, charm, skill, achievements, basically everything. Unlike a large majority of Redwall villains, he never seemed to lose his temper, to go crazy or lose his nerve at a critical point, or to come across an obstacle he couldn’t plot (or, more appropriately, weasel) his way around. He spent more time planning than fighting, never bothered to waste time quarreling (what’s there to quarrel about? Cross him and you’re dead), and always fought “smart” – ie. in the dark, using poison, or catching his enemies by surprise. His cool, collected manner and sneaky, manipulative methods of inquiry always kept him in complete control. He also has perfect aim with his throwing knives and never misses, which is pretty refreshing since the “perfect aim” genes usually favor the good guys in Redwall. In my opinion, no other villain before him or after came even close to nearly overthrowing the most fortified stronghold in all of Redwall.
Smaug from The Hobbit by J. R. R. Tolkien: Smaug is the poster child for charming, cunning, silver-tongued mythological creatures who enjoy witty banter, clever dialogue exchanges, matching wits, and general messing with you for fun… that is, until they get bored enough of playing around and decide to turn you into ashes. He may seem like a laid-back, intelligent, and worthy conversational opponent, but Smaug isn’t kidding around when it comes to being dangerous, greedy, and murderous. If it weren’t for that silly hole in his otherwise impenetrable hide, he would have easily destroyed the entire city of Laketown and all our heroes. I love Smaug though. He took the mountain singlehandedly and defended it far better than anyone else. Despite hiding away in a mountain for years basically taking one long power nap, he kept dwarves, men, elves, orcs and (sure, why not?) eagles at bay without lifting a claw. And he didn’t let himself go either–the flames, the mind, the muscles, etc. all seem to be in pretty good shape when Bilbo turns up. You gotta admire that kind of mental and physical fortitude.
Long John Silver from Treasure Island by Robert Louis Stevenson: Ohh, this guy. Of all the villains on the list, LJS is the one who most seems to get off scot-free. He is the master of flattery and double-crossing, starting with (actually probably starting well before this, but this is the first one I recall) getting himself a job as a seacook for the treasure hunt, all the while secretly planning to take over as captain and then to betray whoever he has to to end up with both the gold and his neck intact. He doesn’t seem particularly malicious or deadly, just greedy and selfish, but he is so good at feigning concern and friendship with others that it’s easy to forget that every word out of his mouth is a cunning lie designed to manipulate the hearer into a less advantageous position. Even his fondness for Jim rather conveniently ingratiates him with the more upright side of society, just in case his plans go awry. He may relinquish some of his dignity in playing both sides and flattering and fawning over whoever happens to hold the upper hand, but he knows how to stay alive and how to play the game to his advantage, leaving it to others to fight with swords and guns while he can usually get what he wants just with his tongue. He also gets credit for being smart enough to know when to cut his losses and hightail it out of there with as much gold as can fit in his pockets. Respect.
Maleficent from Sleeping Beauty: Don’t think Maleficent is capable of seducing you and winning you over? What if I said SHE ALREADY HAS? Wait, that wasn’t the plot of the Angelina Jolie movie? Sorry, I haven’t seen it. Anyway, let’s stick with the original greenie meanie queenie, the Maleficent of 1959. If you haven’t seen this movie in a while, you really should. It holds up. And by “it,” I mainly refer to just how awesome of a villain Maleficent is. Her dialogue is intelligent, cunning, and she usually gets the final say. She has a killer evil smile and appearance, a repertoire of sarcastic, witty comebacks, and her delightfully creepy musical motif is just the right amount of a soft, quiet threat combined with a sudden, dramatic, unstoppable attack. Fittingly, her sneaky, evil, spying crow could definitely outwit the majority of stupid, klutzy Disney villain sidekicks. With so much power at her fingertips (as we see later when she’s in full fire-breathing and thorn-spell-casting form), it’s surprising to see how much Maleficent relies on inflicting emotional pain & deeply thought-out, intricate, long-lasting methods of punishment for those who get on her bad side: Pricking your finger on a spinning wheel and falling into a forever death-sleep 16 years after a pretty mild social offense committed by your parents? Setting up your victim to be captured at the very moment and place where he thinks he’s meeting his true love? That’s some creative thinking. Not to mention her delightful dripping-with-cruelty speech to Prince Philip, where she coolly reveals her plan to release him to find his true love after he becomes frail and loses his mind from a lifetime of imprisonment. Yes, Maleficent is one magnificently evil villain, and my admiration for her goes a long, long way. Better invite her to your next baby christening party, just in case.
Satan from Paradise Lost by John Milton: Satan is the definition of a villain who seduces and destroys. A master of rhetoric and seduction, a likeable and energetic speaker, and a clever, wily, powerful character, he is instantly the most interesting and exciting part of the book and you can’t help but wonder if he doesn’t have a point. He’s the first major character we are introduced to in the poem and he makes a strong case for being the protagonist, fighting for his doomed cause to the best of his abilities and defending his position with a complicated and sympathetic re-interpretation of events. We are convinced and charmed by his attracting and compelling exterior, but there are concealed consequences to joining his cause which he does not present. If we join him, we too will fall. By giving Satan such an attractive and persuasive personality, Milton really opens our eyes to how easy, how rational, and how deadly it is to give in to temptation.