There’s something fun about bad guys. A memorable villain is just as much a key ingredient of literature as the hero, acting as the antagonist and obstacle in the way of the heroes goals. If done properly, a villain will be just as remembered and often as beloved as the hero, hailed for their command of evil minions, nefarious lines, and the threatening situations they put our plucky main characters in. But who are the best? Who are the cream of the crop among literary bad guys? Well, here are the top ten best and darkest villains in literature!

10. Annie Wilkes- ‘Misery’ 

Image via Stephen King wiki

Annie Wilkes is a cautionary tale, showcasing how mentally unstable being a ‘superfan’ can make you. When writer Paul Sheldon breaks both legs in an accident, Annie takes him in and begins to nurse him back to health. But slowly, she reveals she’s obsessed with the Misery series Paul writes and the latest book kills off Misery. Annie Wilkes snaps at this and forces Paul to write a new novel that undoes Misery’s death. She subjects him to multiple horrors within her house, such as slicing off Paul’s leg with an axe and stabbing a state trooper who tries to rescue Paul before running him over with a lawnmower. Annie Wilkes grows increasingly psychotic over the course of the novel and just as Paul does, the reader becomes increasing desperate to escape her presence. Annie Wilkes was played by Kathy Bates in the 1990 film adaptation, winning an Oscar for bringing the character to life.

9. Patrick Bateman- ‘American Psycho’

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Debuting in 1991 in the novel American Psycho, Patrick Bateman is a deeply, deeply disturbed man. A young investment banker living in Manhattan during the 1980s, Patrick Bateman is a serial killer who begins the novel in semi-control of his killing urges but spirals completely out of control as the novel progresses. Told from Bateman’s POV, the novel paints him as a racist, a homophobic, a narcissist, and a psychopath. However, Bateman may not even be a serial killer, as the novel frames his crimes as possibly not even having happened after he confesses at the book’s end. Nevertheless, there is no doubt that Bateman is a deeply disturbed man and one whose mental state is at rock bottom, even if he’s a serial killer or not.

8. Count Olaf- ‘A Series of Unfortunate Events’

Image via Lemony Snicket wiki

Children’s novels often have brought to life some of the most iconic villains in pop culture and Count Olaf is no exception. The main antagonist for the majority of the series, obsessed with claiming the fortune of the Baudelaire orphans. Over the course of the series, he appears in each location the children find themselves in, from steel mills to a reptile zoo to a carnival. Each time, Count Olaf assumes a new disguise in his pursuit of the kids, fooling everyone but them with his distinct personas. He may be a murderer with a flair for arson but Count Olaf is always a lot of fun, hammy and over the top in his villainy. Yet, at the end of the series, he manages to become a sympathetic figure and even allies with the children against a worse evil before he meets his demise, showing perhaps that he was more complicated than we thought.

7. Big brother- ‘1984′ 

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Less a character than a symbol of tyranny and oppression, Big Brother is nonetheless the ruling leader of Oceania in 1984. Never seen in person, Big Brother might just a symbol of the tyrannical Party but that doesn’t matter. People believe he exists and the Party reinforces this belief to the oppressed populace. Posters decorate the city that bear the now famous slogan ‘Big Brother is watching you’. The message is always clear: Big Brother sees all and if there is dissent, he knows. Big Brother becomes akin to God, a portrait of a tyranny realized at its terrifying conclusion.

6. Mr. Croup and Vandemar- ‘Neverwhere’

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Croup and Vandemar are a double-act, a pair of villains who are hired to track down the heroes in Neverwhere. It is not made entirely clear what they are but they’re not human, that’s for certain, as they have a habit of eating live animals and sometimes, chunks of furniture! Croup is a small fat man who is possessed with a verbose style of speech while Vandemar is his brutish partner who barely speaks and specializes more in killing things. The pair certainly make a memorable impression whenever they’re onscreen, serving as an excellent and terrifying pair of evil thugs who can’t be stopped by regular weapons.

5. Regal Farseer-‘The Farseer Trilogy’

Regal Farseer is a vain and cruel prince in line to acquire the throne in the fantasy kingdom of Buckeep. However, his plans of ascension are thrown into a snag when a bastard son of his father, Chivalry Farseer, called Fitz (the protagonist) comes to Buckeep. Regal is aware of Fitz’s heritage and plots to kill him. He eventually acquires the throne throughout the trilogy and Fitz is brought into conflict with his half-brother to get it back. Regal embodies jealously, cruelty, and arrogance, being one dark and vicious prince.

4. Randall Flagg-‘The Stand’

Described as Stephen King’s ‘ubervillain’, Randall Flagg appears through Stephen King’s multiverse to wreck constant havoc. He first appears in The Stand, as a demonic cult leader trying to establish a new society filled with his loyal followers after a plague has destroyed the Earth’s population. Flagg seemingly meets his end when his blown up by a nuclear warhead but reappears throughout further Stephen King works, revealing himself to be an immortal sorcerer who travels throughout space and time, his ultimate goal being to climb The Dark Tower to become a god. Assuming a vast number of identities, Flagg is always a manipulative, dark presence who strikes fear whenever he appears, no matter the setting or genre.

3. Professor Moriarty- ‘Sherlock Holmes’

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Even if you’ve never read a Sherlock Holmes story, you know this guy. Moriarty appears in The Final Problem, becoming famous as the antagonist who would (temporarily) kill Sherlock Holmes. There, Holmes has penetrated his criminal organization and is forced to flee across the country from Moriarty’s wrath. The pursuit ends on Reichenbach Falls, where the two fight and seemingly plummet to their deaths. Moriarty never appears directly onscreen, as the novel is narrated by Watson who never crosses path with the criminal leader but he is practically an overlord of the London underworld, just as brilliant as Sherlock but uses his mind for evil. It’s no wonder Moriarty was promoted to Holmes’s archenemy, he became such an iconic figure that adaptations see fit to use him as Sherlock’s ultimate enemy.

2. Dolores Umbridge- ‘Harry Potter’

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Forget Voldemort, Dolores Umbridge is a far more evil character because of how real she feels. Seemingly a sweet little lady, Dolores Umbridge reveals herself to be sadistic, cruel, and hits all the buttons to make her hate throughout the series. She interrupts Dumbledore during the Feast, she speaks to the students as if they’re a bunch of small children, she punishes Harry for his misbehaving by making him carve the words “I MUST NOT TELL LIES” over and over again into his skin while she watches with a sweet smile. Dolores hides behind her position of authority to inflict her sadistic whims on Hogwarts and its a sigh of relief when gets what’s coming to her at the end, although some think it wasn’t enough for this woman.

1. Sauron- ‘The Lord of the Rings’

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The titular Lord of the Rings, Sauron is unique among fantasy evil overlords in that he never appears directly in the trilogy but his presence consumes everything and he’s responsible for every evil act in one way or another. A former Maiar, a divine angel, Sauron turned away from the light in his lust for power and crafted the One Ring to rule Middle-earth. But the forces of men and elves fought against him, destroying his physical form. Sauron took years to establish himself again, confining himself to his tower in Mordor and building a dark army to conquer Middle-earth while searching to regain the One Ring to claim ultimate victory. Sauron is arguably scarier for how he never appears, only referenced by Gandalf, Saruman, and Gollum but the way they speak of him, how they describe what he is, leaves no doubt that he is one of the greatest villains in literary history. Sometimes, the imagination is more powerful than what we can see.