Literature's Ten Most Disturbing Sociopaths

10. Becky Sharp — Vanity Fair by William Makepeace Thackeray

Skills: Bilingual (French and English), lovely singing voice, talented pianist and actress, witty and charming—you'd be tempted to cast her in a Broadway rendition of Les Mis.

Dirty deeds: Becky is what the hip-hop crowd would refer to as a natural-born hustler. An orphan whose goal is to increase her social standing, regardless of what it takes, Becky seduces other women's men, steals from creditors, pulls a variety of financial cons, helps her husband cheat other men at cards, and quite possibly murders someone for the insurance money. She's unable to bond or show true affection to anyone, even her own son (who she neglects and bullies) and husband (who she leaves in detainment so that she can sleep with another man to further herself socially). All of this without an iota of guilt. In some circles, Becky is considered a feminist icon, but ladies, if this is what you aspire to, please take me off your mailing list immediately.

Quote: Lady Jane describes Becky as "a wicked woman—a heartless mother, a false wife ... She never came into a family but she strove to bring misery with her and to weaken the most sacred affections with her wicked flattery and falsehoods ... her soul is black with vanity, worldliness, and all sorts of crime. I tremble when I touch her. I keep my children out of her sight."

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9. Anton Chigurh — No Country For Old Men by Cormac McCarthy

Skills: Inescapable, relentless, and damn near indestructible. Able to withstand broken bones and other injuries that would bring down a normal guy. Enjoys and is good at his job, so that's, um, nice.

Dirty deeds: This cold-blooded assassin with "eyes like wet stones" digs killing people (mostly by smashing holes in their skulls with a captive bolt gun) so much that he has been known to take out the people who hire him. Chigurh ruthlessly exacts revenge on the world at large, taking lives with absolutely no remorse and sometimes determining whether or not to murder someone based on a coin toss.

Quote: "When I came into your life, your life was over."

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8. Tom Ripley — The Ripliad series by Patricia Highsmith

Skills: Hobbies include forgery, gardening, painting, traveling, boating, art, impersonations, and creative methods of murder (bashing with boat oars, ashtrays, etc.).

Dirty deeds: If Becky Sharp from Vanity Fair had a Match.com profile, she'd probably get paired up with Tom Ripley. Then one of them would kill the other before the third date. C'est la vie. Like Becky, Tom is an orphan who has his eye on the prize: a life among society's elite. Not content to be a NYC con artist, Tom finds a rich dude, murders him with a boat oar, and takes over his life. Over the course of five novels, Tom—described by Highsmith as "suave, agreeable, and utterly amoral"—lives the high life using dead dude's cash and callously murders anybody who starts to suspect he's a fraud.

Quote: "The fact that I killed this man—It's not going to change my life."

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7. Hannibal Lecter — Red Dragon and others by Thomas Harris

Skills: Licensed psychiatrist, extreme charmer, Epicurean, bibliophile, music lover, foodie—if you didn't know about the cannibalism and serial killing, you'd be tempted to invite him to your next dinner party. Just don't serve Chianti.

Dirty deeds: Yet ANOTHER orphan (note to writers: not all sociopaths need to be orphans), Lecter watched his sister get cannibalized when he was eight. Apparently that does bad things to a person's head. He kills every man who played a part in his sister's death—so far, it's a vigilante story not too far removed from The Crow or Batman—but he doesn't stop there. He goes on to become a prolific serial killer and blood-thirsty cannibal, later escaping from prison by cutting off a guard's face and using it as a mask. Presumably, that's easier and more subtle than stealing a guard's hat and keeping your head down.

Quote: "I collect church collapses, recreationally. Did you see the recent one in Sicily? Marvelous! The facade fell on sixty-five grandmothers at a special mass. Was that evil? If so, who did it? If he's up there, he just loves it, Officer Starling. Typhoid and swans - it all comes from the same place."

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6. Frank — The Wasp Factory by Iain Banks

Skills: He's Scottish, so probably has a cute accent... aside from that, not a lot of redeeming qualities.

Dirty deeds: We meet Frank at the age of 16 but find out that he's already been busy, killing three kids before the age of ten but explaining that "it was just a stage I was going through." (Oh, kids! You're so crazy!) He fashions a contraption that forces wasps to choose the method of their demise (Burning? Drowning in urine? Being chopped up? Eaten by a spider? So many options!) and ritualistically kills larger animals to put their heads on "sacrifice poles" around the island where he lives. Still, his father and brother make him look like a picture of sanity. Don't read spoilers for this book, btw.

Quote: "Of course I was out killing things. How the hell am I supposed to get heads and bodies for the Poles and the Bunker if I don't kill things? There just aren't enough natural deaths. You can't explain that sort of thing to people, though."

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5. Iago — Othello by William Shakespeare

Skills: Accomplished liar, master manipulator, Machiavellian schemer—you know, the sorts of things you'd look for when hiring a lawyer, not an advisor.

Dirty deeds: Othello's "honest" and trusted advisor, Iago might have even been a contender for employee of the month until he was passed up for a promotion; then all hell broke loose. He plots to take down Cassio (who took his promotion), convinces his boss that his wife is cheating, and plans to use deception to destroy Othello without detection. That's all before he murders his ally and convinces Othello to kill his own wife. One Shakespeare scholar said, "evil has nowhere else been portrayed with such mastery as in the evil character of Iago." That's a bold statement given the range of Shakespeare's villains.

Quote: "The Moor is of a free and open nature, That thinks men honest that but seem to be so, And will as tenderly be led by the nose, As asses are."

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4. Cathy Ames (aka Kate Amesbury) — East of Eden by John Steinbeck

Skills: Specialist in depraved sexual desires and good at mimicking actual emotions, so she'd do great in the porn industry

Dirty deeds: Finally, a sociopath on our list with loving, dutiful parents... until she kills them by burning down the house while they're in it. Cathy believes everyone to be as evil as she is; thank god she's wrong. As a young woman, she drives one of her teachers to suicide, seduces a married man, and frames two young boys for rape. She spends her life manipulating men for her benefit (going so far as to sleep with her husband-to-be's brother on her wedding day), eventually marrying a man who she shoots after unsuccessfully trying to abort his twins with a knitting needle. When asked if she'd meant to kill her husband, she snipes, "If I'd wanted to kill him, he'd be dead. Just ask my parents." She bails on her family, changes her name to Kate Amesbury, and goes to work at a brothel where she befriends the madame to get into the woman's will then slowly poisons her to death. She turns the brothel into a den of depravity that focuses on the darkest sexual desires and keeps blackmail material on her clients. When one of her sons finds out that his mother is, in fact, not dead but running some kind of goth-y center for sexual freakiness, he kills himself. Cathy/Kate is unmoved.

Quote: “I believe there are monsters born in the world to human parents ... And just as there are physical monsters, can there not be mental or psychic monsters born? The face and body may be perfect, but if a twisted gene or a malformed egg can produce physical monsters, may not the same process produce a malformed soul?"

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3. Alex — A Clockwork Orange by Anthony Burgess

Skills: Strong leadership qualities and a knack for bizarre slang

Dirty deeds: Alex and his droogs' antics were so hardcore, referring to them as violent wasn't enough. Their nights of ultra-violence included assault, rape, stomping homeless people, robbing stores, vicious beatings, and worse. When he finished drugging and raping 10-year-olds or murdering old women, Alex spent evenings chilling in his apartment, fantasizing about more violence while relaxing with some classical music. Even jail wasn't enough to reform him. He beat an obnoxious cell mate to death and was, therefore, selected to take part in an experimental technique designed to turn him away from the dark side. The whole thing is just a real horrorshow.

Quote: “They don't go into what is the cause of goodness, so why of the other shop? If lewdies are good that's because they like it, and I wouldn't ever interfere with their pleasures, and so of the other shop. And I was patronizing the other shop ... I am serious with you, brothers, over this. But what I do I do because I like to do.”

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2. Kevin — We Need to Talk About Kevin by Lionel Shriver

Skills: Archery, hatefulness—he'd be great at the Hunger Games but is horrible at life

Dirty deeds: Described as “a shell game in which all three cups were empty” with “an apathy so absolute that it's like a hole you might fall in,” Kevin was cold and contemptuous when he came out of the womb. His most potent venom is reserved for his mother, who has another child just to be able to connect with another family member (if you're on the fence about having kids, read this book first), but Kevin's asshole tendencies don't stop with his mom. He convinces a girl to gouge her own eczema-affected skin, kills his sister's pet hamster, and is suspected of destroying his sibling's eye with drain cleaner. Despite all these shenanigans, his father decides that archery would be a great hobby for the young psychopath. We don't want to spoil a good book for you, but it's not too much of a jump to say that things end badly. Very badly. For a lot of people.

Quote: "...You can only subject people to anguish who have a conscience. You can only punish people who have hopes to frustrate or attachments to sever; who worry what you think of them. You can really only punish people who are already a little bit good.”

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1. Patrick Bateman — American Psycho by Bret Easton Ellis

Skills: A successful investment banker and stylish dresser with an extensive knowledge of eighties music and an eye for interior design—a real mover and shaker

Dirty deeds: In between comparing business cards and drinking cocktails with other investment bankers, Patrick busies himself with senseless murders and stomach-turning torture sessions. After killing a colleague, he loses control of his violent urges and moves on to necrophilia, cannibalism (making meatloaf of a girl is frustrating!), mutilation, and horrific murders involving chainsaws, nail guns, and rats (holy shit, the rats). Bateman's charm, complete detachment, and lack of emotion or remorse make him the most disturbing sociopath on our list. There are things here that can't be un-read.

Quote: “...there is an idea of a Patrick Bateman, some kind of abstraction, but there is no real me, only an entity, something illusory, and though I can hide my cold gaze and you can shake my hand and feel flesh gripping yours and maybe you can even sense our lifestyles are probably comparable: I simply am not there ... Is evil something you are? Or is it something you do? My pain is constant and sharp and I do not hope for a better world for anyone. In fact, I want my pain to be inflicted on others. I want no one to escape.”

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