Mutilate a pumpkin, carve a pentagram on the floor, it's Halloween – the one time of year we get to celebrate the darker side of things.
But what is it about great villains that we adore so much? Simply: vice is a hell of a lot more glamorous than ordinary, boring, bed-by-nine virtue.
Maybe it has something to do with the sheer variety of devilry that we find so alluring – the monsters under the bed, the serial killers at the window, the beasts that lurk inside our darkest fears. Or, to mutilate Anna Karenina's famous principle: all saints are alike; each sinner sins in its own way.
But how do you choose a favourite? Well, we couldn't, so we chose 50 instead. Happy Halloween.
Blood Meridian by Cormac McCarthy (1985)
Seven-feet tall, bald as a pebble and as remorseless as Death himself, The Judge might be the most terrifying character in literature. He never sleeps, dances and fiddles with the gusto of a man half his age and murders children. He's an albino enigma and the physical embodiment of eternal war. Basically Moby Dick in cowboy boots.
The boy with the scissors
The Paper Dolls by Julia Donaldson (2012)
In this gorgeous children's book about the beauty of memory and dealing with death, a little girl loves her string of paper dolls. Until, that is, a little boy comes along with a pair of scissors and – snip, snip – chops them into pieces. Don't let his rosy cheeks and rainbow scarf fool you: he's pure evil, Death made flesh... he'd might as well be dressed in a black hood and cloak.
IT by Stephen King (1986)
The homicidal harlequin of Hell himself – Stephen King's dream clown with the “clotted, chuckling voice” who invites children to “float” in the sewers with him. And by “float” he means he'll drag them to his subterranean lair where he'll feast on their fear until they're face-down in dirty water.
My Sister the Serial Killer by Oyinkan Braithwaite (2018)
Ayoola is the eponymous sister who carries a knife in her handbag “the way other women carry tampons.” And let's just say she doesn't use it to carve her name in trees. She is beautiful, too, with a body, literally, to die for (“a figure eight — like a Coca-Cola bottle”). And she manipulates her sister Korede into helping her hide the bodies of the boyfriends she remorselessly kills.
Beloved by Toni Morrison (1987)
Recently freed from slavery, Sethe moves into a house that is “full of a baby's venom.” The baby in question, is the one Sethe killed 18 years earlier to save her from the life she escaped. Now, that baby is back to haunt Sethe in the form of a young woman who inveigles herself into Sethe's mind, breathing her “lively spite” through the house – a literal manifestation of Sethe's grief and the horrors of slavery.
Moby-Dick by Herman Melville (1851)
You thought the giant whale was the villain? No, the real evil in Melville's masterpiece seethes deep within the man who wants to kill him. Fuelled by toxic vengeance for the white leviathan that took his leg, Captain Ahab's only love in life is hatred – for the whale, for dry land and, above all, for himself.
The Sea Witch
The Little Mermaid by Hans Christian Andersen (1837)
Looking for everlasting love? Simple, just pop down to the bottom of the sea and the Sea Witch will see you right. The only catch? She'll cut out your tongue; give you legs that cause you unimaginable pain when you walk; and, if you fail to win the love of a dreamboat prince, you'll die of a broken heart and dissolve excruciatingly into sea foam.
Red Dragon by Thomas Harris (1981)
The cannibal king of literature. The emperor of anthropophagy. The gourmand of gastro-murder. Hannibal Lecter is never satisfied with merely killing you; his savagery is far too sophisticated. No, he must sautee your brains and pair your liver with “fava beans and a fine chianti”. That, or just convice you to kill yourself with his psychiatric powers.
The Birds by Daphne du Maurier (1952)
The birds don't need weapons to kill you – they were born with beaks, bills, nebs and mandibles. If they were capable of complex emotions you'd call them angry. But they're not capable of complex emotions, they're driven only by an ineffable compulsion to peck you to death because you're a human and they are birds – a vast and emotionless horde of blood-lusting birds.
American Psycho by Brett Easton Ellis (1991)
He's the ginning face of Wall Street, a monster with a gold-trim business card; far less turned on by “mergers and acquisitions” than he is by “murders and executions”. Shudderingly remote from human life and driven by an unquenchable lust for blood and sexual power, Bateman pleasures in turning murder into art, and our stomachs to mush.
The Picture of Dorian Gray by Oscar Wilde (1890)
Dorian Gray is an unquestionably awful guy – certainly not the type you'd want to visit your first Chinese opium den with. But vanity is the real villain in Wilde's classic. And once Gray drinks from vanity's cup, it bleeds through his soul like red wine on a wedding dress.
Dr. Faustus by Christopher Marlow (1592)
The Devil's messenger, Hell's keeper of secrets and, more importantly, its contracts. You want everything you ever dreamed of in life? Sure, he can arrange that for a small price. That price, of course, being your body and soul, consigned to the fires of Hell for the rest of eternity.
The Grand High Witch
Psycho by Robert Bloch (1959)
He's a psychotic serial killer who dresses up as his dead mother and murders people thinking he is her. And as if that weren't creepy enough, he keeps her mummified corpse in his motel for company.
The Silver House
White is for Witching by Helen Oyeyemi (2006)
The notion of a haunted - or haunting - house has been a crucial part of female-written gothic literature since it emerged in the late 18th century. But Helen Oyeyemi gave it a fresh lick of paint in 2009 with her chilling coming-of-age novel. The Silver House causes its residents to behave uncannily, it's true, but Oyeyemi deftly shows that there are just as many very real horrors lurking outside its walls, too.
Ring by Koji Suzuki (1991)
She's the vengeful ghost of a psychic girl brutally murdered by her father and left to rot at the bottom of a well. But her psychic powers cannot be curbed by something so trifling as death. So she returns in the form of a cursed video tape to wreak vengeance on all humanity. Once watched, the tape will kill you in seven days... unless you pass it on to someone else.
Cruella De Vil
The Hundred and One Dalmatians by Dodie Smith (1956)
If you were scared by The Texas Chainsaw Massacre – about a deranged killer who wears the skin of his victims on his face – imagine how dogs must feel about Cruella de Vil. The embodiment of sloth and greed, she is selfish, spoiled and has a volcanic temper... and her sole purpose in life is to skin dogs and wear them as couture.
The White Witch
The Chronicles Of Narnia by C. S. Lewis (1950-1956)
She can hear your thoughts, turn dissenters to ice, control the seasons and her cackle carries on the wind like an untreatable airborne virus. But you're still not convinced of her sheer purity of evil, consider this: she cancelled Christmas. Need I go on?
The Woman in Black
The Talented Mr Ripley by Patricia Highsmith (1955)
The real horror inside Tom Ripley is that he's so polite, likeable and charmingly starry-eyed, you find yourself willing him to succeed in his campaign of remorseless manipulation, murder and identity-theft.
We Need to Talk About Kevin by Lionel Shriver (2003)
A psychopathic misanthrope of the highest order, Kevin is a morality vacuum who hates his mother, goads a girl with eczema into gouging her own skin, and possibly behind the "accident" that left his sister without an eye. Then he massacres a group of children after luring them in his school's gym. If there were ever an argument that some people are just born evil, Kevin is it.
Titus Groan by Mervyn Peake (1946)
Calm, calculating and driven only by his own self-interest, he creeps about the crumbling corridors of Gormanghast castle manipulating and murdering his way to the top. As one character observes when she looks into his eyes: “Close-set nostrils they were, not so much eyes as narrow tunnels through which the night was pouring.” The original worm-tongue of duplicity, and one of the creepiest baddies in fiction.
Matilda by Roald Dahl (1988)
A headteacher who hates children? There are plenty of those in the real world, but none who hates them so much that she denies having ever been one herself. And certainly none who takes such pleasure in publicly humiliating her wards, throwing them over fences for wearing pigtails or force-feeding them cake in assembly is, in Dahl's words, "more like an eccentric and rather bloodthirsty follower of the stag-hounds than the headmistress of a nice school for children".
Uncle Tom's Cabin by Harriet Beacher Stowe (1852)
Literature is not short of monstrous slave owners, but Simon Legree is down there with the worst of them. He is as happy to have an enslaved person whipped to death for believing in God as he is to spur an unbroken horse refusing a saddle. He is a sexual predator and a violent sadist – one of the vilest characters in all literature.
Few figures in The Handmaid's Tale are more ruthlessly terrifying than Aunt Lydia, the imperious instructor who brainwashes, manipulates and tortures handmaids into obedience. But what makes her truly horrifying is not just her cruelty, but also her gender: a woman (a former family court judge, no less) indoctrinating other women into sexual servitude under Gilead's violently patriarchal new world order.
Kindred by Octavia Butler (1979)
He's a slaveowner with a conscience, which only makes him more despicable. Rufus Weylin is petulant, needy and selfish – a pathetic mysoginist who craves the love of his enslaved people but also doesn't mind raping them so long as the pretend they enjoy it.
Something Wicked This Way Comes by Ray Bradbury (1962)
Mr. Dark will grant you your wildest dreams in return only for your soul to fuel his sinister travelling carnival where laughter goes to die. Want to be young again? Sure, you just have to ride his creaky merry-go-round backwards, to the tune of the funeral march, to take a year off your age with every revolution. The only catch: you must live in a child's body with the mind of an old person forever. But his covenants are bespoke, and he'll find the payment that best fits your needs.
Jaws by Peter Benchley (1974)
She's the teeth of the sea, the monster of the deep blue, the hulking mass of murderous flesh that will rise silently from the dark and tear you limb from limb because that's just what evolution has hardwired her to do. The book (and the subsequent movie franchise) caused Benchley such guilt over the shark stigma he spawned that he became a shark conservationist in later life.
The Lord of the Rings Trilogy by J. R. R. Tolkein (1954)
If you've ever lost your wedding ring down the kitchen sink, you have an idea how of Sauron felt. The all-powerful necromancer is what happens when Big Brother gets a little too obsessed with jewellery, and will stop at nothing to get his bling back. Of course, anything's easier to find when you have an all-seeing eye that “pierces cloud, shadow, earth, and flesh”. And plugholes, presumably.
Brighton Rock by Grahame Green (1938)
A teetotal 17-year-old Catholic gang leader who roams wind-swept Brighton armed with a razor blade, a bottle of acid and a hatred for all humanity (especially women), Pinkie is the embodiment of pure evil – the Devil with a baby face.
You by Caroline Kepnes (2014)
A truly dedicated villain grabs you by the throat and tightens his grip page by page. Joe Goldberg is that villain, a stomach-turningly vile manifestation of unconscionable evil and sexual predation. He is a psychopath and a misogynist who sees women only as the sum total of their sexual organs. He hates women, while also wanting to possess them entirely. That, of course, starts with stalking and ends in kidnap, imprisonment and murder.
The Demon Headmaster
The Demon Headmaster by Gillian Cross (1982-present)
A headteacher who wears sunglasses can mean one of two things: he's either desperately hungover, or he's a megalomaniacal alien warlord who uses his glowing green eyes to hypnotise his victims in his bid to take over the world. Either way, the sunglasses are a definite red flag.
The Nickel Boys by Colson Whitehead (2019)
The cruelty inflicted on the students at the nightmarish Nickel Academy comes from nearly every aspect of life at the school – and every aspect of that life is controlled by Maynard Spencer, its abusive, manipulative superintendent.
The Woman in White
Pine by Francine Toon (2020)
Perhaps the strangest thing about the woman in white that haunts Pine is the fact you quite want her to return. The ethereal presence at the heart of Francine Toon's debut novel leaves the feeling of kisses, an animal smell and precious trinkets for her loved ones. But who is she, and why is she there?
Perhaps only one so terrifying could prove so ripe for reinvention. More than a millennium on from Beowulf's publication and the fearsome monster at its core continues to provide inspiration. Contemporary illustrations may prompt comparisons to the Gruffalo, but be careful - mess with Grendel and face his mother, an arguably more terrifying presence.