Stephen King probably has the most iconic mix of villains of any horror creator. Yes, Wes Craven has both Krueger and Ghostface, and John Carpenter has Michael Myers and the blue-skull aliens, but let’s be real. King comes out on top for his sheer variety of colorful, nightmare-inducing, iconic, sexy characters.

Hold up, did I say sexy? That can’t be right. Oh…it seems I did, and that can only mean one thing: a smash or pass ranking of Stephen King’s most iconic villains. Pennywise the Clown and Leland Gaunt can steal your soul, but can they steal your heart? And just to clarify the ranking, we are going solely on the characters themselves, not the actors who have portrayed them.

SMASH or PASS: Stephen King Villains Edition

SMASH: Annie Wilkes

Yeah, she’s crazy, but come on. She loves to read, is resourceful, and knows her way around… a sledgehammer? Just don’t kill off her favorite character, and you’re safe. Her farmhouse also seems super cozy, so any time spent there would be lovely. As long as she doesn’t have any problems with my screenplays, I’ll take my chances.

PASS: Leland Gaunt

This is the hardest pass on this list. Everything is a mind game with this guy. Sure, he’ll pay for dinner, but he’ll probably later make you pay him back by stealing a dog or performing some other bizarre task. Everything would be a bargain and transactional. With no clear communication, he is actually the worst imaginable partner on the list. Besides, according to the book, he is a reptilian demon riding a white horse? Check, please…

NEUTRAL: Pennywise

Pennywise’s attractiveness varies wildly. This interdimensional shapeshifter can be literally anything…Sure, Bill Skarsgard is plenty attractive, and his take would absolutely be a smash, but knowing there’s a cosmic spider under there might be a turn-off. He is also a cannibalistic chaos demon, but so are half the characters on this list. You win some and lose some when you open Tinder in Derry, Maine.

PASS: Randall Flagg

Every iteration of Flagg going back to the books has portrayed him as really hot. So why a pass? Well, his whole character is built on the concept of false promises. He feels like your worst ex-situationships. Always promising something bigger, he is a total manipulator who will use you for his own power. Also, he looks real nasty with the devil horns…and not in a good way.

SMASH: Christine

Hear me out. Let’s ignore the fact that she’s a cosmically possessed car. Christine is loyal, loving, and protective. Sure, she’s manipulative and pure evil, but she is obsessed with you. Flagg, for instance, would dump you the second he got what he wanted. But Christine wants you and only you. Maybe that’s worse, given you now have to walk down the aisle with a 1958 Plymouth Fury. But hey, if you don’t have commitment issues, Christine might be your gal.

PASS: Jack Torrance

Going off of the book, it’s a no, solely because when he qualifies as a villain, he is possessed by a sentient hotel. In the movie, he is psychotic from the start of the film. There is no way to spin the possessed Jack Torrance in a positive light.

SMASH: Kurt Barlow

I have no defense for this. I just have a good feeling about him. How can you say no to those eyes! Vampires are sexy. Well, some vampires. I feel like he has kind of an Eggers’ Nosferatu appeal? You LITERALLY cannot resist him. So hey, this seems to be a SMASH whether I want it to be or not.

PASS: Warden Samuel Norten

Unlike most of the villains on this list, Norten is not a fun, supernatural being. This is a real kind of evil. There is not even a joke to be found with this one-this guy sucks. Pass on all accounts. What does it say about your politics when I would rather take my chances with an interdimensional spider-clown?

SMASH: Rose the Hat

Does this even need an explanation? Rose is BY FAR the most attractive Stephen King villain. Sorry Mike Flanagan, the eerie little glowing eyes are kinda hot. I am sure that was not your intention. But here we are. As long as you don’t have the shine, you should be safe. Not sure if I would be down to join her weird RV demon-polycule, but otherwise, it’s a done deal. Actually, you know what? Why the Hell not. Let’s get some shining-mist together!

SMASH: The Creep

It’s so hard to find funny guys, right? Not anymore! The Creep is a total jokester. Funny, intelligent…what’s not to love? Well, the rotting skin and exposed skeleton can be a turn-off, but no one’s perfect. It’s what’s on the inside that counts!

Ah, Urban Legend…the plucky younger sibling franchise to Scream. If this is the first time you realize that it’s a franchise at all, that is totally fair. The cult classic slasher’s only theatrical sequel was a critical and box office flop. The third film, Bloody Mary, was direct-to-video. The film has an interesting comparative pitch to Scream. While Scream is a meta-slasher toying with the rules of horror, Urban Legend has its killer basing its slice-and-dicin’ off of famous urban legends…and then they just basically did a version of Scream 3 for its sequel. It’s a fascinating trilogy, particularly in how the movies connect. In Final Cut, the first film exists as an urban legend itself. Bloody Mary, however, is a complete standalone that could be read as an urban legend within the universe of the first entry.

The Urban Legend Franchise Ranked From Worst to Best

So…how do these three films rank against each other? Are the sequels worth checking out at all? Pull up a chair, relax, and start mixing your Pop-Rocks and soda; this is the worst-to-best ranking of the Urban Legend trilogy.

Urban Legends: Bloody Mary (2005)

Unsurprisingly, the straight-to-video, nearly completely forgotten supernatural entry is last. Directed by Mary Lambert of Pet Sematary acclaim, the movie is a straightforward supernatural horror. Three teen girls say “Bloody Mary” three times into a mirror, and it resurrects a vengeful spirit.

The movie is not terrible by any means. It is just pretty standard, with some good moments of schlocky, 2000s fun. For those that grew up in this era, it can be a goofy little nostalgia trip! The cheesy SFX, hilariously awkward teen acting, and cinematography of a Coke commercial make it a really easy watch. It’s almost like a much bloodier Goosebumps episode! However, for those not fans of this divisive era of TV-horror, it can be a bit of a slog.

The idea of making a movie that feels in-Universe to the first film is clever. However, it is unclear whether that was the exact intention. Despite this critic’s personal, nostalgic love of this film, it is not connected to the franchise at all. Even if this was a masterpiece, this detail makes it hard to put it anything above last place. Sorry Bloody Mary, I still love you.

Urban Legend (1998)

Ready the guillotine. Light up the torches. Find the IP address this article was written on-but let me explain. Yes, it is controversial not to put this one in first place. Still, it is really more of a tie than second placement. This and Final Cut are vastly different, which makes the franchise interesting, nearly incomparable. They each succeed in their own sub-genres…but this one misses the mark.

Urban Legend is a cult classic for a reason. It is completely itself as a late-90s, teen campus-slasher. The movie takes a simple premise, combining it with a likeable cast and a gothic, dark-academia setting. It feels like it was made for slumber parties and sleepovers. A combination of 80s slashers and campfire tales? Amazing. Plus, the soundtrack is killer.

That being said, the mystery, story, and characters are all just okay. The answers to the mystery (spoilers…?) fall in line with I Know What You Did Last Summer, and many films from the 80s. Prom Night, April Fool’s Day, and The Burning all come to mind. If this came out before Scream, this would be number one, for sure. It is probably, technically, the best film of the franchise, if I had to be objective. However, it just doesn’t reach the levels of originality the final film on this list does.

Urban Legends: Final Cut (2000)

Urban Legends: Final Cut is fantastic. No, really. It’s great, and one of the most underrated slashers of its time. While Scream picked apart the slasher genre in a meta-horror classic, this movie picks apart the horror film industry. The film has a lot of commentary on toxicity in the industry, and it is matched by an on-brand mystery.

A big issue with movies is finding a decent throughline. Look at the first Urban Legend, for example. The reason the killer kills has nothing to do with urban legends themselves-it is just a creepy MO. However, the killer in Final Cut has a motive rooted in filmmaking itself. The movie stays on brand, delivering on its promise. It is distinctly different from Scream, while still being perfect for fans of that franchise.

Without spoiling, the mystery is great. While the final reveal is somewhat predictable, the twists and turns of the story itself are great. For fans of lost media horror like Red Rooms or Cigarette Burns, the mystery veers into that. One part of the film involves a student film with a mystery splice in the film spool. While the movie is funnier than it is scary, and somewhat outdated at points, it still feels the most rewatchable of all three movies.