Is there a human being on this planet who has f’ed up an entire generation harder than Stephen King? Nay, generations.

Trick question: There is only one answer and that answer is “no.”

Millions of us read our fair share of King as kids and spent too many nights wide-awake because of him. It was the way he wove terror into mundane, everyday situations, but more than that, it was his memorable villains. They slithered tentacles into our heads and hooked clawed hands into our hearts. But which of his monsters caused the most lasting emotional trauma? Which ones haunted us and never left? Faced with these burning questions, I decided to rank Stephen King’s villains in order of how much they messed you up as a kid.

Before we begin, a note: Some of these monsters are from his novels, some from his short stories. Some of these are helped by great movie adaptations. Obviously, I can’t include every single one here, because, well, I have a life to lead and need to do things like sleep and eat. I narrowed down the list by pulling from his more memorable or recurring villains. We’re all about painstaking scientific accuracy here.

With those parameters set, let’s dive in.

13. Cujo

Appeared in: Cujo

Rabid St. Bernard Cujo in the movie adaptation of the classic Stephen King novel (Courtesy: Warner Bros.)

Cujo: NOT a Very Good Boy (Courtesy: Warner Bros.)

Cujo might be one of the most memorable characters Stephen King has ever written and he’s not even human – or human-like. He’s certainly the most famous dog. The image of a crazed, murderous St. Bernard is one that lingers, but Cujo was just a dog with rabies. And rabies is something a kid can understand. It falls under the umbrella of things that can happen in real life, but let’s be honest – it’s still highly unlikely. Cujo was scary, but not that scary because he fits into the realm of what a kid’s mind can easily understand. For that, he gets last place on this list.

12. Annie Wilkes

Appeared in: Misery

Kathy Bates as the murderous Annie Wilkes in 'Misery' (Courtesy: Columbia Pictures)

Annie Wilkes, the Patron Saint of Toxic Fandom (Courtesy: Columbia Pictures)

Similar to Cujo, Annie Wilkes is a villain one can’t fully understand and appreciate until adulthood. Sure, Annie is obsessed and nuts, but she’s still entirely human, and human is – mostly – normal. If I were making this list an overall list or one for adults, she’d rank much higher. Annie Wilkes was a prescient creation of King, a precursor to the days of entitled fandoms making death threats and doxing creators. But as a kid, she just comes across as a crazy lady. You wouldn’t want to be kidnapped by her, but thoughts of her weren’t keeping you up at night.

11. Jack Torrance

Appeared in: The Shining, Doctor Sleep (ghost)

Yes, Jack Torrance is also just human. Unlike Annie, he doesn’t even start out as psychotically violent. He’s a completely normal husband and dad, just down on his luck. But that’s what makes his transformation into a murderous monster all the more terrifying as a kid. Adults are supposed to safeguard children; parents are supposed to be protectors. That’s how the world is supposed to work. So the story of a father who, through supernatural forces far beyond the ken of a kid, slowly descends into madness and tries to murder his family is chilling, especially when driven by Jack Nicholson’s unhinged performance in Kubrick’s movie adaptation. The one person you rely on to keep you safe is the one trying to kill you: That’s a heavy load for the kid brain to handle.

10. Henry Bowers

Appeared in: IT

Henry Bowers in the 1990 'IT' miniseries (Courtesy: Warner Home Video)

A childhood tragedy turned into a monster (Courtesy: Warner Home Video)

Henry Bowers is the most realistic creation on this list; his horror doesn’t stem from any supernatural forces. Instead, he’s just a good, old-fashioned bully from an abusive home, and that’s what makes him scary – not because a situation like his is wholly fantastic but because it’s all too common. Almost every school has a malicious kid that seems designed only to cause misery and pain to those weaker than them. But the double horror for a kid is when you learn that Henry himself is being abused by his father. There’s no one to protect him and there’s no one to protect other kids from him. That’s messed-up.

9. Blaine the Mono/Charlie the Choo-Choo

Appeared in: The Dark Tower III: The Waste Lands, The Dark Tower IV: Wizard and Glass

Charlie the Choo-Choo, the fictional real-world inspiration for Blaine the Mono

Yeah, NOPE. (Courtesy: Simon & Schuster)

Leave it to Stephen King to take a beloved children’s character (in this case Thomas the Tank Engine) and warp them into something depraved. The thought of being trapped on Blane the Mono, a sentient train that had slowly gone insane over the centuries, was scary enough. But when you combined that with Charlie the Choo-Choo, a children’s book in the Dark Tower universe loosely based on Blaine, it became even more terrifying. That ghoulish imagery of the sentient train smiling his sinister smile in a twisted mirror image of Thomas was enough to haunt our dreams. And haunt them for a while.

8. Tak/Collie Entragian

Appeared in: Desperation, The Regulators

Ron Perlman as possessed Sheriff Collie Entragian (Courtesy: Lionsgate Home Entertainment)

Collie looks great, for a person possessed by a demon (Courtesy: Lionsgate Home Entertainment)

Similar to how parents are supposed to watch over you, kids grow up believing that cops are good guys there to protect them – at least, in a just world. But the killer sheriff of a tiny desert town in Nevada is there only to kill, and he has no compunction about murdering kids. That Collie Entragian is simply possessed by a demon, Tak, somehow makes it even scarier. Police officers are supposed to be invincible, invulnerable, the pillars standing between order and the bad things lurking. That one could be corrupted so easily breaks down the structural integrity of a kid’s understanding of the world.

7. Kurt Barlow

Appeared in: ‘Salem’s Lot, mentioned in The Dark Tower V: Wolves of the Calla

Ancient vampire Kurt Barlow in the 1979 movie adaptation of 'Salem's Lot' (Courtesy: Warner Bros.)

Kurt Barlow definitely doesn’t sparkle (Courtesy: Warner Bros.)

Everyone’s done vampires, and will continue to do them. Stephen King was, in many cases, a kid’s first introduction to the grotesque, old-school version of vampires that had been out of vogue for decades. Kurt Barlow was ancient and he looked it, neither sparkly-pretty like a Twilight vampire, nor elegant like Bela Lugosi. Instead, he was a Nosferatu-like creature, all shriveled claws and a jutting mass of pointed teeth. He didn’t appear much in the novel at first, but the times he did appear, he was so overwhelmingly powerful that there was no standing against him. A monster in the most fundamental sense of the word, he created a lasting impression on kids.

6. Margaret White

Appeared in: Carrie

Margaret White forcing Carrie to pray for her sins (Courtesy: Scream Factory)

Margaret White, praying for her daughter’s evil soul. As you do. Totally normal. (Courtesy: Scream Factory)

Stephen King sure likes parents who would regularly make the Worst Parents Ever list. Margaret White’s religious fanaticism was terrifying, Even as a kid, one glimpse of her empty-eyed gaze told you something was deeply, deeply wrong with her, even if you couldn’t quite articulate why. Like an apple that had gone all worm-rotted on the inside, you somehow just knew if you dug beneath the surface of Margaret White, nothing but black worms would come out. The abuse she doled out to her daughter Carrie was simply the manifestation of that rot. Margaret White showed you love can warp into something dark and sick when it’s confused with religious fundamentalism of the most extreme sort. What kid wouldn’t be terrified by the image of a mom who hysterically laughs as she tries to stab her daughter? Not one.

5. Zelda Goldman

Appeared in: Pet Sematary

Andrew Hubatsek played Zelda in the 1989 movie as women weren't angular enough (Credit: Paramount Pictures)

Fun fact: Andrew Hubatsek played Zelda in the 1989 movie; they couldn’t find actresses angular and bony enough (Credit: Paramount Pictures)

I know, I know, Zelda Goldman isn’t a villain. Even so, I’m putting her on this list not because of the original novel, but because of the 1989 film adaptation. The late sister of Rachel Creed, Zelda had died when she was young from spinal meningitis. In the novel, it’s brought up in flashbacks. As a kid, it’s hard to grasp the true horror of the situation. You just knew it was a bad medical condition. But then the 1989 film came along. The reveal of Zelda’s disfigured and emaciated body was a powerful body horror punch. And to think of her dying on you, right in front of you? Zelda symbolized the fear not of death, but of disfigurement and the grotesque. She was ultimately a sympathetic character, but try telling a kid that when a gurgling mummy lady is making a death rattle.

4. Randall Flagg

Appeared in: Too many novels and short stories to name

Just a few of the many faces Randall Flagg has worn over the millennia

Walter O’Dim. The Dark Man. The Man in Black. The Walkin’ Dude. Marten Broadcloak. Walter Padick. The Ageless Stranger. The Grinning Man. The Man With No Face. Randall Flagg has gone by many names and lived many lives in many worlds. As a demonic entity, he is Stephen King’s version of Lucifer and his most enduring antagonist. The ubiquitous villain has appeared in various guises all throughout King’s novels and short stories. The only reason Flagg doesn’t rank higher on this list is because he’s usually portrayed as a charming tempter with charisma for days. There are moments King lets Randall Flagg’s true evil creep through and in those moments, he is terrifying. Adults don’t forget that. But it’s easy as a kid to forget that when Flagg’s entire existence hinges on him hiding the monstrousness lurking just beneath the surface. His charm lulls you into forgetting just how evil he really is.

3. He Who Walks Behind the Rows & The Boy Preacher, Isaac

Appeared in: Night Shift short story “Children of the Corn”

Really nails the dead-eyed stare, doesn't he? (Courtesy: Anchor Bay)

Really nails the dead-eyed stare, doesn’t he? (Courtesy: Anchor Bay)

The short story was scary enough, but truly, this is the one entry on the list that benefited most from the movie adaptation. There’s something really, really freaking terrifying about an evil that is so incomprehensible to the human mind that it doesn’t even get a real name, just an ancient-sounding, mythical moniker. It was even more terrifying as a kid to realize it was other kids who had turned into a murderous cult and were worshipping him. Kids were supposed to be the normal ones! It’s adults who were mysterious and weird doing their adult things. The blood-soaked child preacher, Isaac, is one of the most chilling portrayals of religious zealotry ever depicted on screen because of how far he was willing to go to appease He Who Walks Behind the Rows. A deity so powerful and malevolent that it could convince an entire town of children to sacrifice their parents in cold blood was unsettling to the bone. And a kid like Isaac, so willing to go along with it? Even more terrifying.

Oh, and P.S.? King has never confirmed nor denied it, but there is a theory that He Who Walks Behind the Rows is none other than Randall Flagg himself.

2. The Boogeyman

Appeared in: Night Shift short story “The Boogeyman”

The Boogeyman is the stuff of childhood nightmares

The Boogeyman is the stuff of childhood nightmares

What monster haunts more childhoods than the boogeyman? Stephen King’s version is a Boogeyman with a capital “B.” It is the monster to end all monsters, the first creature under the bed, the first boogeyman in the closet. The Boogeyman doesn’t just scare kids; it kills them. Smothers them until they stop breathing or snaps their necks while they sleep. As a kid, reading about the screams of other kids as they were stalked by the monster you thought lived under your own bed was horrifying. The slithery, leathery sound the Boogeyman made as it moved in and out of closets sounded just like the things you heard at night in your own room. And the final reveal that it could just…be anywhere, in any closet, anywhere in the world? That was a creature to haunt the darkest of your childhood nightmares.

1. Pennywise

Appeared in: IT, mentioned in other books

And this is why clowns are "punch on sight" status for me

And this is why clowns are “punch on sight” status for me

Come on. You knew Pennywise had to be #1. He is Stephen King’s most terrifying Big Bad, and it doesn’t matter what age you are. Adult, teenager, kid, Pennywise the Dancing Clown is the stuff of terror, the very embodiment of the rips in the fabric of reality. King tapped right into the fundamental, uncanny valley fear that clowns trigger inside us…and then he kept digging. A monster that only kids could see, a shapeshifter that pulled your deepest fears right out of your head, Pennywise wrecked the sleep of an entire generation of kids. In the pages of the book, he was terrifying enough. But when the 1990 miniseries came out, Tim Curry’s portrayal made Pennywise even more real. Seeing him in the flesh, the corpse-pale greasepaint and the balloons, crystalized the horror that was the ancient evil. Because of it, we’ll never look at storm drains or red balloons the same ever again. And now, Stephen King creepy go-to Bill Skarsgård is carrying on the tradition and terrifying an entirely new generation. No kid who has ever stumbled across Pennywise under the age of 13 has ever been the same again. That’s why he is #1 on this list. Forever.

IT: Chapter Two is in theaters on September 6th.

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