5 Pennywise (It)
Coulrophobia – That’s the fear of clowns. The TV miniseries adaptation of Stephen King’s novel, It, is not a film to cure one’s coulrophobia. For within that film, is the masterful performance of Tim Curry, who portrays the titular evil force’s favorite embodiment, Pennywise The Dancing Clown. Whether luring small children into sewers, or issuing threats from inside textbook illustrations, Curry’s fanged, clawed merrymaker made an impression on anyone who saw this production at any point in their youth. Curry, no stranger to evil incarnate, having played the Lord Of Darkness in Ridley Scott’s Legend, brings his A game here, resulting in a character far more remembered than the rest of the film he inhabits, even more so than most horror icons.
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/is related to the 19th landowner’s daughter whose love he died for, then 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.
3 Freddy Krueger (Nightmare On Elm Street)
No matter how talkative and silly Freddy got over the years, the power of both his method and motive never paled. A monster that strikes at you in your sleep, where you have nowhere to run but as far 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 rubbing out whatever Elm Street kids he didn’t get around too, 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 one of the most potent mythologies in all of horror. Whether played by Robert Englund at his campiest and most pun-spouting, or 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. There officious and articulate leader, (former British explorer who found the box in an Egyptian pyramid long ago) Pinhead (Doug Bradley) 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 known as the Lament Configuration. 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 (The 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. Myers was pulling the whole “silent un-killable juggernaut “ act a full 3 years before Jason Voorhees first donned his hockey mask, and 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 characters 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.
Chucky (Child’s Play) – A serial killer transfers his soul via voodoo ritual to a child’s doll in order to escape the police. You were scared.
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.