Top Five Favorite Fictional Villains

[SPOILER ALERT: There may be unintentional spoilers revealed though I’ve done my best to minimize discussing major plot points. But be aware nevertheless.]

Heroes are what most stories are about, but one character who can make or break a story for me is the villain.
mean ruthless bad villain
I would go so far as to say that a story is really only as good as its villain. When you think about it, the villain is the chief threat for the hero. If the villain is weak, then there isn’t much for the hero to do and the story suffers for it. But if the villain is strong and a nearly equal match to the hero, then the story will be rife with drama and tension (or at least it should). Thus, most of my favorite stories usually contain a very memorable baddie.

For this post, I’m going to explore my top five favorite villains from print fiction (but who may have since been adapted to film or television) and I will be breaking down each villain by exploring seven areas:
Appearance – What does the villain look like?
Backstory – What are the villain’s origins?
Why He’s Bad – What are the qualities, deeds, etc. that make this character a villain?
Good Points – Does this villain have any qualities that are good in and of themselves?
Why I Like Him? – Why does this villain belong on my list?
Memorable Moment – What is this villain’s most notable scene?
Would I Want to Meet Him? – If I could meet this person, would I dare?

So with that out of the way, on to the list! 🙂

#5 – Penguin/Oswald Cobblepot (Batman comics and sundry adaptations)
Penguin has been depicted in a variety of ways, starting with a campy but often dark version in the comics to various visual media adaptations ranging from a young adult incarnation (Fox’s “Gotham”) to a kooky Gothic look (Batman Begins). (Though the strangest take for me is when Penguin is given a British accent in the game Batman: Arkham Knight. Seriously, that just doesn’t work – at all.) Collectively, and regardless of source material, traits common to Penguin are an Old World fashion sense, short stature, beak-like nose, an ever-present umbrella, and typically a rotund build. But while Penguin isn’t built to be a lean street fighter (and his stature and features rightfully earn him his avian nickname), that by no means implies he’s any less mean.

Backstory: Penguin’s story has some alterations depending on the medium but the premise is essentially the same. Penguin’s real name is Oswald Cobblepot and, while he remained the apple of his mother’s eye as a child, he wasn’t liked by anyone else. (In some variations, Oswald’s father dies from a bout with pneumonia after getting caught out in the rain, which led to Oswald’s mother insisting that he tote an umbrella with him at all times.) Frequently bullied, Oswald had to craft a hard outer shell, as well as cultivate a cunning mind, to outsmart and seek revenge upon his oppressors. This sense of self-preservation through schemes and a desire for control eventually propelled Penguin to be one of Gotham’s top crime lords.

Why He’s Bad: Penguin, a classic DC super-villain, is a crime boss who has no problem crushing his competition but often hires others to do his dirty work. While Penguin may not take a hands-on approach to his schemes, he is the brains behind them and can often see several steps ahead of his “enemies.” He’s also not above making deals with the police or Batman. So in exchange for having them look the other way when it comes to his illegal businesses, Penguin offers valuable intelligence on his competition. All in all, Penguin has the cool, level-headed business sense of a Mafia don and will do whatever it takes to secure his place on Gotham’s throne of crime.

Good Points: Penguin’s foresight is certainly admirable. In the same way, he doesn’t let bullies get the better of him, which, in isolation, is respectable as he defines himself on his own terms. Likewise, he can do good that he doesn’t intend. Because Penguin often gives Batman or Commissioner Jim Gordon information to help put other baddies behind bars, his actions, by proxy, help clean up Gotham. However, Penguin doesn’t do these things for the good of his fellow Gothamites – he does it for his own aims. But the removal of a criminal element is still the removal of a criminal element, no matter who is sending them packing. So that alone helps keep Penguin from being a truly despicable villain.

Why I Like Him: While the Joker commonly earns top spot among favorite Batman villains, mine has always been Penguin because his schemes and crimes are concocted and carried out of a generally sane, stable mind. Granted, his methods can be violent and heartless but usually not over-the-top cruel nor utterly depraved. Again, Penguin is a pragmatic businessman who makes decisions based on how to best protect himself and his interests, so bloodletting for bloodletting’s sake alone doesn’t appeal to him. But he always manages to exploit other’s weaknesses to advance his own cause. However, at times he can do good that he doesn’t intend, showing that his moral compass, however sorely misguided it is, is not entirely off-kilter.

Memorable Moment: Some of the best moments that pull back Penguin’s hardened layers occur in Pain and Prejudice, a graphic novel. Here, Penguin meets and woos Cassandra, a blind woman for whom he feels genuine affection but believes he has to buy her love with expensive (and usually stolen) gifts. His interactions with her expose his inner workings as Penguin isn’t so frigid that he can’t love – he just doesn’t understand what true love means and, sadly, never seems to learn.

Would I Want to Meet Him?: Maybe, but I really think it would depend on the incarnation – some I think I could hang with, some I would just give a polite nod to and cross to the other side of the street.

tenmen_charTen Men McCracken
#4 – The Ten Men (The Mysterious Benedict Society trilogy by Trenton Lee Stewart)
These gents win the award for Best Dressed on this list. Always donning expensive suits, accessories, and cologne, the Ten Men opt for a classy look as one of their assets is the ability to blend in and pose as common businessmen. They’re almost always outfitted with a briefcase containing assorted weapons (crafted from office supplies) and don two shock watches, one on each wrist, that can electrocute potential victims. While the trilogy doesn’t give too many detailed descriptions, in general these dangerous gents are described as “handsome” and giving off a congenial, casual air that masks their cold, calculating ways. While a few of the named Ten Men’s physical features or attributes are isolated, it’s McCracken, the head Ten Man, who gets the most attention. He’s the leader and for good reason as his size and strength, as well as his “piercing blue eyes” and “perfectly coiffed” hair, are often emphasized. (After all, any guy who is described as “a huge man with shoulders like bedside tables” better be the leader, right?) Collectively, the Ten Men dress the part of villains – even if they’re only henchmen – and have the weapons and physical strength to back it up.

Backstory: In the first novel, The Mysterious Benedict Society, we see the early origins of the Ten Men as Recruiters, chiefly men hired by Ledropatha Curtain to “recruit” (i.e. kidnap) children and bring them to his Institute. Hinting to their later incarnation as the Ten Men, Recruiters wear nice suits, shock watches, and go overboard with the cologne. Their eventual disbanding and renaming as the Ten Men comes from the fact that they have ten ways to inflict harm. Early on, only one female Recruiter is mentioned but never named; and in the second and third books, the Ten Men are exclusively an all-boys club, which is appropriate considering the various dangerous tasks and assignments they carry out on behalf of their boss.

Why They’re Bad: The Ten Men are in the employ of the nefarious Mr. Curtain, who pays them handsomely to be his minions. In fact, the Ten Men follow him solely for a paycheck and because they enjoy destroying things and hurting people. On that note, Mr. Curtain often brings McCracken in to help plan some of his schemes and McCracken seems willing to lend aid but often delivers a good dose of sarcasm, implying he doesn’t strive for the same aims as his employer. Despite their seemingly one-track motivations, the Ten Men are clever, ruthless, and cunning. McCracken also displays a certain ability of foresight as, on many occasions, he can predict the moves of the “enemy” before nary a move is made. Thus, these gents are bad to the bone and possess a brain to boot though evidently don’t react to the element of surprise very well (implying they’re more methodological in their approach).

Good Points: Their negative qualities double as positives: they’re intelligent; good at reading people; capable trackers; can see through ruses, misdirection, and lies; and hold their own in a fight, whether it’s out in the open or in close quarters. In isolation these are good qualities, but the Ten Men always put them to nefarious use, which makes them treacherous indeed.

Why I Like Them: The Ten Men are classic henchmen figures but they’re not stupid and approach their line of “work” with a calm, casual air combined with a polished exterior. This gives them a sinister quality that, in some respects, is more frightening than Mr. Curtain’s presence since they pose more of an overt, physical danger to the lead characters. Thus, they’re  professional, smart, dedicated henchmen rather than goofball, goof-up bad guys. Also, the fact they don’t use guns and knives – in favor of killer pencils and exploding calculators – softens their image to make them suitable for kids while still being formidable and very dangerous.

Memorable Moment: This occurs about midway through the second novel in the trilogy, The Mysterious Benedict Society and the Perilous Journey, where we see a whole slew of Ten Men corner and capture the four lead characters. This also marks McCracken’s formal entrance and his banter with the kids is wittingly threatening. It perfectly encapsulates everything professional and ruthless about the Ten Men.

Would I Want to Meet Them?: Maybe. Just within a good running distance in case they decided to use their shock watches or throw a lethal pencil. McCracken certainly sounds swoonworthy, but essentially these are gents to observe from a distance.

Negan 1Negan (JDM)
#3 – Negan (The Walking Dead comics, adapted for television)
Negan is depicted as a physically imposing man, so it makes sense that he’d be in a leadership position. He’s noted for having a chiseled face and dark hair and eyes (in the comics). For the television adaptation, Negan is played by actor Jeffrey Dean Morgan, a casting choice I think was completely spot-on. And while no comic-to-screen casting is ever going to be a perfect match, I think Morgan is as close as you can get without hiring a clone to play the part (and I don’t think we want any Negan clones running around). In both versions, ever by Negan’s side or in his hand is his trusty barbwire-covered baseball bat named Lucille with which (or maybe “with whom” because Negan talks to and about her like she’s a person) he can inflict death and destruction with a single swing. He’s also known for touting an extremely foul mouth and can use the f-word as every part of speech known to the English language. Much like in A Christmas Story where Ralphie’s father “worked in profanity the way other artists might work in oils or clay,” so does Negan dabble in the art of sarcastic wit, sadistic humor, and no-bounds swearing.

Backstory: Robert Kirkman, creator of The Walking Dead comics, presents Negan’s pre-zombie apocalypse occupation as a teacher/coach who apparently wanted to be perceived as the “cool” teacher. He was also married to a cancer-stricken wife (yet this evidently didn’t stop him from cheating on her). (Just to note, this backstory is taken from the Here’s Negan mini-comics Kirkman is publishing, which are not included with the usual Walking Dead issues.) In the actual Walking Dead, comics Negan is the fearless, fierce king-like leader of the Saviors. This band of survivors exists under a system of give and take where they do far more of the latter and far less of the former: they protect surrounding communities from Walkers (i.e. zombies) in exchange for a portion of the communities’ supplies, always taking more than what they really need. Those who refuse them or fight back are punished in unreasonably cruel ways. Negan’s philosophy is that he’s actually doing these communities a service by using strong-arm tactics in exchange for offering them protection. However, Negan seems to possess some remnants of a heart as he takes a non-creepy liking to Rick Grimes’ son, Carl; has a genuine distaste for sexual violence; and, while he amasses a harem, doesn’t abuse his wives (though he demands sexual faithfulness).

Why He’s Bad: Negan employs a sense of twisted logic where he forces people to do what he wants them to under the guise that he’s open to negotiation. In reality, the communities he bullies are put in a bind – give in to Negan’s demands or pay the consequences, often with a tragic loss of life. In truth, Negan isn’t 100% psychopathic – he will listen to a reasoned argument albeit he doesn’t feel compelled to agree with it and probably won’t. That being said, he has a taste for violence and shows no mercy towards anyone whom he feels has slighted him or broken his rules.

Good Points: The fact Negan wants to establish at least some sense of order amid chaos is, in and of itself, admirable. Likewise, his governing philosophy, while morally murky, is that rules keep people safe. He also has a strong disgust of sexual violence, calling it “unseemly,” as one of his rules is, “We don’t rape.” Lastly, his charisma enables others to follow him (though swinging a barbwire-covered baseball bat will probably have something to do with it, too).

Why I Like Him: Negan is nearly a pure psychopath as he ultimately acts in his own self-interest, feels little remorse or guilt, displays violent behavior, and can adopt an empathetic attitude with a disarming and charismatic air. However, I say nearly because Negan assumes a quasi-paternal attitude towards Carl. Granted, it’s rife with his usual brand of profane humor, but ultimately Negan doesn’t do Carl any real harm and, later on, even agrees to help fight against some common enemies. Thus, there seems to be a strand of good inside of Negan that prevents him from becoming 100% evil. Still, he truly is “mad, bad, and dangerous to know.”

Memorable Moment: This would be when Negan dialogues with Carl for the first time. Granted, he’s playing a twisted mind game, but ultimately I think Negan takes a genuine liking to Carl and is impressed by the young man’s sheer nerve. It also marks a rare soft-hearted moment when, after profanely insisting that Carl remove a bandage that conceals a terrible wound, Negan suddenly feels sorry for Carl when the boy starts to cry. Negan is a man of few chinks in his emotional armor, but when they come out they add a layer of depth to his character.

Would I Want to Meet Him?: To be honest, he’s kind of cool but very dangerous. Basically if you appease him and stay on his good side, then maybe you could hang out and play ping pong. Otherwise, keep your distance – especially from Lucille.

Pitch art from booksPitch from Book
 #2 – Pitch (The Guardians of Childhood by William Joyce)
Pitch is a shadow-covered figure who is human in form yet technically not Human (more on that in a moment). The book’s illustrations often depict Pitch as having dark, flyaway hair and donning shadowy armor and/or garments. He’s tall and lithe, much like the way a shadow exaggerates a person’s shape, and he carries himself with a noble air that immediately lets you know this is one villain you don’t want to cross.

Backstory: Pitch’s real name is Kozmotis Pitchiner and he was originally from the constellation Orion, so he’s technically an alien or, at the very least, otherworldly yet Human in appearance. Pitch served as a commander of celestial armies that fought against the Dream Pirates, insidious beings that brought nightmares to life. Being a defender of the right and the light, Pitch battled these nefarious foes until they got the better of him. Realizing Pitch’s family was his heart’s weakness, the Dream Pirates schemed to kill Pitch’s wife and little daughter. Before their assault, Pitch’s daughter sneaks aboard a star boat and sails away to safety. In the meantime, her mother sacrifices herself by devising a ruse so the Dream Pirates believe both she and her child have died; and though Lady Pitchiner does not survive, she knows her daughter is safe. Satisfied, the Pirates later brag to Pitch of their victory, resulting in their immediate execution by his hand. This results in Pitch vowing revenge on the dark forces that destroyed his family and he stations himself as the sole guard of a prison where shadowy nightmare beings called Fearlings are held. In time, Pitch is deceived and, in a moment of weakness, becomes possessed by the same dark forces he hates.

Why He’s Bad: Pitch is the Nightmare King who commands a vast array of dark beings and is capable of performing magic to deceive and trick his “enemies.” While I absolutely love the film The Rise of the Guardians, which is based on an original story by Joyce (separate from the novels but using most of the same characters), its version of Pitch is decidedly less dark. In the film, he’s the Boogeyman, a powerful trickster with a playful side, bent on spreading nightmares to children around the world and crushing their belief in the Guardians. His primary grief, as it were, is that no one believes in him. (This isn’t a complaint, mind you, as I suspect this change was to make Pitch more little kid-friendly.) In the books, however, Pitch is a dark force to be reckoned with whose desire is to spread darkness and nightmares to children everywhere simply because he is so consumed with darkness himself.

Good Points: Pitch is very crafty, which points to a high level of intelligence, and he is no amateur at magic. He is capable of using foresight to plan his next move and is very goal-oriented. A final point in his favor is that Pitch has the ability to be redeemed as his daughter seems like the only person who can bring out any softer emotions in him. Thus, Pitch’s heart isn’t 100% black (just 99.9%).

Why I Like Him: Out of all of the villains on this list, Pitch is the only one who started off as a good, noble hero, hence why I believe he can be redeemed. Likewise, Pitch has a compelling backstory that aptly shows how and why he became evil. Unlike most children’s stories where villains tend to be safe, cookie-cutter baddies with no how or why regarding what they do, Pitch breaks the mold by being genuinely scary (but not too scary) and has an origin that explains what drives him. Not to mention it evokes sympathy as Pitch becomes evil, not because he desired to be but because he was taken advantage of in a sense. Thus, Pitch is the only villain you can honestly feel sorry for, which makes him a well-rounded baddie indeed.

Memorable Moment: My choice goes for when we learn about Pitch’s backstory in the fourth book in the series, The Sandman and the War of Dreams – from his time as a commanding officer and family man, to a man haunted by the past, to his rise as the Nightmare King. This keeps Pitch from becoming a villain who is bad “just because” and exposes a human side to his otherwise shadowy heart.

Would I Want to Meet Him?: If he talks like Jude Law (who provided Pitch’s voice in the movie), then absolutely! Otherwise, I think I’d steer clear.

Lord Voldemort 1 Lord Voldemort 2
#1 – Lord Voldemort (Harry Potter series by J.K. Rowling)
As a youth, Tom Malvolo Riddle (Voldemort’s real name) is described as handsome but that quickly disappears when he allows his ugly inner desire for power to manifest itself. Using magic, Tom transformed himself to mimic the very creatures he held so dear – snakes (as, being a parselmouth, he can talk to snakes). After this change, Voldemort sports serpentine facial features, including slit-like pupils and nostrils, and an overall waxy appearance. Seemingly tall, thin, but undeniably imposing, Voldemort commands respect from his followers and elicits fear from those who would dare to defy him.

Backstory: Tom was the son of Merope Gaunt, a witch from an abusive household, and Tom Riddle, a handsome Muggle (i.e. non-magic-wielding person). When Riddle left, effectively abandoning his wife, Merope did her best to survive while pregnant with her son. Finally, she gave birth in an orphanage and died soon after even though she had the power to save herself. Young Tom grew up without knowledge of his heritage until Albus Dumbledore showed up at the orphanage’s door and Tom was welcomed into the magical world at Hogwarts School for Witchcraft and Wizardry. However, even at an early age Tom had a habit for using his magical skills for ill, from stealing trinkets to being a terrifying bully. In time, he honed his dark talents, renamed himself Lord Voldemort (an anagram of his full name), and amassed followers known as Death Eaters. In time, Voldermort became a deadly threat to the Wizarding community, committing murder and leaving mayhem in his wake.

Why He’s Bad: Lord Voldemort, for me, is one of the best fictional villains of modern times as he is the epitome of and a model for the perfect Svengali villain. Voldemort essentially has everything you need to make a great baddie: a desire for power and control; cold, calculating logic; an utterly frigid, unsympathetic heart; the ability to read minds and detect lies; cleverness; impressive rhetoric; sympathetic backstory; and an aim to spread death and destruction. Combine all of that with the ability to do some of the darkest magic imaginable, and you’ve got yourself one almost unbeatable foe.

Good Points: I will give Voldemort credit for this – he is not an idiot. His deductive reasoning abilities are incredibly high as are his foresight and ability to plan. He’s charismatic enough to gather followers yet retains them by ensuring their loyalty. Not to mention he’s a powerful wizard. These are all good things in and of themselves, but combined with the sheer badness that is Lord Voldemort, they cease to be anything positive.

Why I Like Him: Lord Voldemort is just bad. As in really bad. Which is why he’s my number one villain. Like Pitch, his backstory is tragic but he made his own wrong choices as a youth to do evil and abuse others, which carried over into his adult life. Likewise, Voldemort is the type of villain you want to see defeated and not redeemed because there is no good left in him. While in the final book Harry asks Voldemort to “try for some remorse” and essentially repent of his wicked ways, Voldemort is simply befuddled and refuses. So from start to finish, Lord Voldemort is a quintessential baddie – the very worst of the worst.

Memorable Moment: Lord Voldemort has a bunch of great scenes, but if I had to choose just one it would be his rebirthing in Harry Potter and the Goblet of Fire. The first time I read those chapters, I thought it was truly creepy and knew this was a villain nobody could touch. Voldemort’s acting like a near-messiah during these scenes is sinister to the nth degree and his confrontation with Harry foreshadows how the two of them would be destined to battle one last time. Until these moments, we never really get to see Voldemort as a character, but this stands out as a character introduction that certainly makes a big, and frightening, impression.

Would I Want to Meet Him?: Are you crazy?!? In a word…
Duck No shake head no way



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