Freddy vs. Jason vs. Pinhead vs. Pennywise: These Are the Scariest Horror Film Villains of All Time

Freddy from Elm Street. Jason from Friday. These names are bound to cause a shiver down your spine, as they are the names of some of the scariest horror film villains.

Some of the scariest horror film villains who have haunted the American horror film space are varied in origin, appearance, motivation and method, but they all have one thing in common: Keeping movie lovers in the United States captivated and frightened by their grotesqueness and cutthroat intent.

Most of these movie villain fiends have created names for themselves as some of the scariest horror film villains in the American horror movie hall of fame.

Here are five of the scariest horror film villains of all time:

5.) Pennywise (It)

If you have a fear of clowns – which is a condition called coulrophobia – this film might leave quite an impression.

The movie It, which is a screen adaptation of Stephen King’s novel by the same name, features one of the scariest movie villains of all time in the character of Pennywise, which was played by Tim Curry.

In the movie, the character of Pennywise is either luring children into sewers or leaving threats in textbooks. He has a variety of powers that allow him to shapeshift into anything his victim fears and be unnoticed by adults, and he appears every 27 years in the fictional town of Derry to attack children.

On developing the character of Pennywise, Stephen King said the creation of one of the scariest horror film villains was based on the fear children had for clowns.

Meanwhile, in the first TV adaptation of the book in 1990, Tim Curry played the evil Pennywise, and we can rightly say that he delivered, as the film was bound to leave an impression on you after watching.

4.) Candyman

Played by the one and only Tony Todd in three films (of descending quality) that bear his name, this lynching victim turned urban legend will appear towering behind you when summoned in a mirror to split you open with his rusty hook. Unless you happen to be a blonde who resembles or is related to the 19th-century landowner’s daughter whose love he died for; in that case, he’ll just whisper to you in a very discomfiting manner about joining him in the afterlife (and maybe also attempt to split you open at some point).

While his tragic backstory makes him more sympathetic than many horror villains, this sensitive artist/romantic nonetheless has Todd’s stature, dead eyes and raspy baritone and is also filled with killer bees, which he can projectile vomit in your direction at will. That’s a recipe for a haunting horror legend, making him one of the scariest horror film villains ever.

3.) Freddy Krueger (Nightmare On Elm Street)

The power of both his method and motive has made Freddy Krueger one of the most popular and one of the scariest horror film villains in Hollywood history. A monster who strikes at you in your sleep, where you have nowhere to run but as far to go as your imagination will stretch, Freddy Krueger liked to kill children during his mortal life.

The parents of Elm Street got fed up one day and fried Freddy alive. Not one to be held back from that which brings him joy, Freddy’s afterlife is dedicated to murdering any Elm Street kids he didn’t get around to before. He does this by seizing control of their dreams. Freddy wants to mess with you before he kills you, which typically involves him manipulating the environment, taking many often humorous shapes and generally turning your own personal fears on you, before your eventual slicing and dicing. It’s all warped beyond belief, and it’s one of the most potent mythologies in all of horror. Whether played by Robert Englund at his campiest and most pun-spouting, or by a more somber Jackie Earle Haley as the lone asset in a very weak reboot, Krueger’s a creep for the ages.

2.) Pinhead and the Cenobites (Hellraiser Series)

You twist that ancient puzzle box, and out they come. A crew of leather-clad, alabaster-skinned, heavily mutilated/deformed humanoids come to rip you apart with hooks and chains before dragging you to hell, where the real pain starts.

Their officious and articulate leader, a former British explorer who found the box known as the Lament Configuration in an Egyptian pyramid long ago, is Pinhead (played by Doug Bradley). He never refuses a summoning and is usually backed up by his friends, The Chatterer, Butterball and the unnamed female Cenobite, each bound by some kind of sadomasochistic worship/enslavement to eternally serve the puzzle box.

Only Clive Barker could have brought us these demonic fetish-heads, who don’t just want to stab you a few times and be done with it:  They want to torture you until time’s end. In hell. Hellraiser is pretty scary.

1.) Michael Meyers (Halloween Series)

Maybe it’s the fact that he’s huge and seemingly invulnerable. Maybe it’s the fact that he wears that creepy Shatner mask. Or maybe it’s the fact that the guy iced his big sister with a kitchen knife when he was six years old. The truth is, it’s all of those things that makes the character of Michael Myers one of the scariest horror film villains of all time.

Myers was pulling the whole “silent unkillable juggernaut” act a full three years before Jason Voorhees first donned his hockey mask, and he is backed up by one of the most menacing pieces of music in popular culture.

When “The Shape” (as adult Michael was originally credited) is unmasked towards the end of the first installment, the dopey looking man-child briefly glimpsed only adds to the character’s eeriness. In the first couple of films, before the series wore on and the character was continually resurrected from so many seemingly insurmountable deaths, Michael walked a line between believable and supernatural that made him an unsettling mystery.

Honorable Mentions

Chucky (Child’s Play) – A serial killer transfers his soul via voodoo ritual to a child’s doll in order to escape the police. This film was bound to make you scared. It is one of the most scariest horror films but with a heavy dose of humor.

Jason Voorhees (Friday the 13th Series) – He’s unstoppable, he’s deformed, and he’s got mother issues. They thought they sent him to hell, but in the future, he went to outer space and got cybernetic upgrades.