Recently, my mom came across an old The Pop of King (Stephen King’s Entertainment Weekly column) post titled “10 Greatest Evildoers in Fiction“. It was King’s own little meme based off of another blogger’s post on the top 10 greatest Stephen King villains.

Taking a cue from my favorite horror novelist, I’ve decided to concoct my own list of literary bad guys. I’ve narrowed it down to the 10 characters whom I feel are most bad simply because they inspire absolutely zero sympathy from me. For example, Voldemort from the Harry Potter series is not in here, as I can find some sympathy for his character. However, Dolores Umbridge from the Harry Potter series IS in this list because I feel that she is far more frightening than Voldemort as she is completely sadistic, unsympathetic, and truly evil. This list is also, obviously, limited to the books that I have read.

10. Gilbert Osmund – The Portrait of a Lady by Henry James

He  hated her for having a mind of her own[…] her mind was to be his.

My list begins with the most awful of husbands! Osmund tricks the very independent and very wealthy Isabel Archer into marrying him, and once she has been trapped, he slowly strips away all that makes her unique and free. She becomes a caged bird, victim to his plot to elevate his own status and power. At 21, Gilbert Osmund terrified me; I made a vow to never be with a man who felt threatened by my own independence and intelligence!

9. Guy Woodhouse – Rosemary’s Baby by Ira Levin

Rosemary Woodhouse: I dreamed someone was raping me. I think it was someone inhuman.
Guy Woodhouse: Thanks a lot. […]
Rosemary: You…you had me while I was out?
Guy: It was kind of fun in a necrophile sort of way.

I take it back! The most awful of husbands is one who would sacrifice your womb to Satan in order to propel his acting career! Guy Woodhouse is abominable! I could take the easy route and state that the Castavets were the major bad guys in Rosemary’s Baby, but it is Guy who is most frightening! Throughout the novel (and famed movie), Guy continuously reassures Rosemary that everything is fine and normal with their Satan-worshipping neighbors and doctor, and urges her to drink all of the nasty herbal drinks provided to her by those same neighbors who are nurturing the demonic child she is carrying. Guy is truly a very bad literary guy!

8. Heathcliff- Wuthering Heights by Emily Bronte

Catherine: Give me that key- I will have it! […]
Heathcliff: Now, Catherine Linton […] stand off, or I shall knock you down […]
Regardless of this warning, she captured his closed hand and its contents again.[…] He opened them suddenly, and resigned the object of dispute; but, ere she had well secured it, he seized her with the liberated hand, and, pulling her on his knee, administered with the other a shower of terrific slaps on both sides of the head…

I know, I know…many readers love Heathcliff. I was actually referred to this book by a friend who thought Heathcliff would top Rochester and Darcy in my beloved socially awkward literary men. How wrong she was! I detested Heathcliff. He sadistically and methodically attempted (and was pretty successful) to destroy the lives of all those around him. I hate Heathcliff!

7. The Man Jack – The Graveyard Book by Neil Gaiman

He had left the woman in her bed, the man on the bedroom floor, the older child in her brightly colored bedroom, surrounded by toys and half-finished models. That only left the little one, a baby barely a toddler, to take care of.

This children’s book is rather frightening. It begins with The Man Jack murdering the family of The Graveyard Book‘s protagonist. The protagonist (the above stated toddler) grows up to learn that this serial killer might still be after him, and sets out to find The Man Jack before he finds him. With creepy illustrations, The Graveyard Book provides one of the most scary bad guys in children’s literature.

 6. Anton Chigurh – No Country for Old Men by Cormac McCarthy

Chigurh: Call it. This is your last chance.
Carla Jean Moss: Heads…
He lifted his hand away. The coin was tails.
Chigurh: I’m sorry.

Anton Chigurh is an enigma. He is a hitman with a method, style, and motivation all his own. He weighs the fates of his potential victims with a coin toss, and those who lose in his game get a captive bolt pistol (most commonly used to slaughter cattle) to the head. He almost seems to have sympathy for his victims, but it would be deluded to believe Chigurh cares. He is a mad man.

5. O’Brien/Big Brother – 1984 by George Orwell

O’Brien: How many fingers am I holding up, Winston?
Winston: Four.
O’Brien: And if the Party says that it is not four but five- then how many?
Winston: Four.
The word ended in a gasp of pain.

O’Brien is the hand of Big Brother in the dystopian classic 1984. He delivers the most horrific torture methods to the protagonist Winston and any other characters who stray from Big Brother’s prescribed way (or lack) of thinking. One such scene involving rats and Winston’s face immediately comes to mind. O’Brien is horrifying in his actions, but readers must remember that he is just a tool of the real bad guy–the all-seeing Big Brother.

4. IT/Derry – IT by Stephen King

“I started after him…and the clown looked back. I saw its eyes, and all at once I understood who it was.”
“Who was it, Don?” Harold Gardner asked softly.
“It was Derry,” Don Hagarty said. “It was this town.”

First, let’s get something straight: Pennywise the Dancing Clown is NOT the bad guy in IT. Pennywise is simply one of the many faces that the otherworldly IT puts on to terrify its victims. IT lurks below the fictional town of Derry and has been in Derry, or rather that location, since Earth’s beginnings. In this way, Derry is IT. The people of Derry, specifically the adults, have been under the influence of IT since, well, always. In this way, the adults of Derry are the true bad guys of IT–they look the other way when the supernatural horrors occur in their town, as well as during the not-so-supernatural horrors of child abuse, extreme bullying, and social terrorism occur. Both IT and Derry terrified me as an 11-year-old reading IT for the first time.

3. Annie Wilkes – Misery by Stephen King

 “My name is Annie Wilkes. And I am-“
“I know,” he said. “You’re my number-one fan.”
“Yes,” she said smiling. “That’s just what I am.” 

Annie Wilkes is nuts! And she delivers what might be the most horrifying acts of violence upon her number-one favorite author. If you want to read real crazy, check Annie Wilkes out in Misery. She might be one of the most talked-about psychotic literary characters of all time–up there with Hannibal Lecter and Norman Bates.

 2. Dolores Umbridge – Harry Potter and the Order of the Phoenix by J.K. Rowling

Dolores Umbridge: Not with your quill, you’re going to be using a rather special one of mine. Now, I want you to write, ‘I must not tell lies.’
Harry Potter: How many times?
Umbridge: Well, lets just say, as long as it takes for the message to- sink in.

Why is Dolores Umbridge so high up on my list? Because she sadistically hurt my precious Harry Potter. Not with a cruciatus curse…that would be too sane. No, during detention, Umbridge forced Harry to dip a quill into his own blood and magically carve “I must not tell lies” into the back of his hand. This scene frightened me, I loved it, I knew the Harry Potter books had finally crossed the line and entered into adult literature. This was as creepy as any Stephen King scene. She definitely left a mark on Harry too…he glances at this scar in the subsequent books with a shudder.

1. Iago – Othello by William Shakespeare

Iago: And what’s he then that says I play the villain, when this advice is free I give, and honest, probal to thinking, and indeed the course to win the Moor again? […] I’ll pour this pestilence into his ear– that she repeals him for her body’s lust […] So will I turn her virtue into pitch, and out of her own goodness make the net that shall enmesh them all.

The granddaddy of all literary bad guys–Iago. He befuddles scholars with his seeming lack of motivation in all of the evil he does (the definition of a psychopath). Does he hate Othello for a promotion slight? Or did Othello sleep with Iago’s wife? Iago never tells it straight, speaks in riddles to himself, and just generally comes off as having no motive for destroying everyone’s lives–just plain psycho! As far as I know, he is the first literary bad guy with psychotic leanings. Thus, he is number one!

There you have it–the top ten literary bad guys. Do you agree with this list? Did I miss someone? Who are your top ten literary bad guys? Please feel free to create your own list and share with me in the comments!