Top 10 Cruelest Fictional Villains of All Time

The Red Queen - Alice in Wonderland

The Red Queen is a fictional character from Lewis Carroll's 1871 novel Through the Looking-Glass. She is often mistaken for the Queen of Hearts from Carroll's earlier work Alice's Adventures in Wonderland, but the two are separate characters with different personalities. The Red Queen is portrayed as... read more

I feel so sorry for Ilosovic Stayne, the Knave of Hearts, that he had to be exiled with her. They either should have given him a second chance or let him kill himself, but he shouldn't have had to live out the rest of his days chained to her.

Off his/her head!

Ursula - The Little Mermaid

Ursula is a fictional character who appears in Walt Disney Pictures' 28th animated feature film, The Little Mermaid, released in 1989. She is portrayed as the main antagonist and is known for her distinctive appearance and dramatic personality. The character's design was inspired by drag queen Divine... read more

She is just creepy! She manipulates Ariel to get revenge on King Triton. She is very evil, but very smart at the same time.
I hate it when she turns giant. Creeps me out EVERY TIME!

The real reason she's evil is because she sounds like a person who had been smoking for 40 years!

Very creepy!

The Joker - Batman

The Joker is a fictional supervillain created by Bill Finger, Bob Kane, and Jerry Robinson, who first appeared in Batman #1, released on April 25, 1940, by DC Comics. Credit for the Joker's creation remains disputed. Both Kane and Robinson claimed responsibility for his visual design, while Finger is... read more

He's insane. He emotionally and physically abused Harley, lies to keep her, harms a lot of people, likes to blow things up, kidnaps people, and forces them to do his bidding. Very cruel villain.

Chucky - Child's Play

Charles Lee Ray is a fictional character and the main antagonist of the Child's Play horror franchise. He becomes the murderous doll known as Chucky after using a voodoo ritual to transfer his soul into the toy. The franchise began in 1988 and has since expanded into multiple sequels and a television... read more

Candyman - Candyman

Daniel Robitaille, colloquially known as Candyman, is a fictional character and the main antagonist of the Candyman film series. The character originated in Clive Barker's 1985 short story The Forbidden. In the film series, he is depicted as an African-American man who was brutally murdered in the 19th... read more

Harley Quinn - Batman

Harley Quinn is a fictional character appearing in American comic books published by DC Comics. She was originally introduced as the Joker's sidekick in Batman: The Animated Series before becoming a prominent character in her own right. Over time, she evolved into an antiheroine and has appeared in numerous... read more

Claude Frollo - The Hunchback of Notre Dame

Dolores Umbridge - Harry Potter

Dolores Umbridge is a fictional character in the Harry Potter book series written by J. K. Rowling. She first appears in Harry Potter and the Order of the Phoenix as a Ministry of Magic official who becomes the Defence Against the Dark Arts teacher at Hogwarts. Umbridge is widely regarded as one of the... read more

She abuses and torments kids because she thinks she can! She's very psychotic!

Jigsaw - Saw

Jigsaw is the alias of John Kramer, a character who first appears in the Saw film series. After losing his unborn child, being diagnosed with terminal cancer, and surviving a suicide attempt, he begins designing elaborate traps to test his victims' will to live. He believes these ordeals help people... read more

He wants to play a game, but it won't be fun. It will be your worst nightmare.

Pennywise - It

It, sometimes capitalized as IT and more commonly known as Pennywise the Dancing Clown, is the main antagonist of Stephen King's novel It and its adaptations, including the 1990 television miniseries and the 2017 film. It is an ancient, shapeshifting, malevolent entity that is billions of years old.... read more

How is this not in at least the top ten? He killed so many innocent children and has caused people who had no problem with clowns to be mortally afraid of them.

He murders children. He even tore a child's arm off. He is the main reason people are afraid of clowns.

?

Dokurobei - Yatterman

?

Handsome Jack - Borderlands 2

Handsome Jack is the main antagonist of both Borderlands 2 and Tales from the Borderlands, and the deuteragonist of Borderlands: The Pre-Sequel. He is the CEO of the Hyperion Corporation and seeks control over the planet Pandora. Known for his dark humor and manipulative tactics, Jack is considered one... read more

Blue Jones - Sucker Punch

Light Yagami - Death Note

Light Yagami is a fictional character and the protagonist of the manga series Death Note, written by Tsugumi Ohba and illustrated by Takeshi Obata. He is a high school student who gains the power to kill anyone by writing their name in a supernatural notebook while picturing their face. The story follows... read more

Lady Tremaine - Cinderella

She turned Cinderella into a slave when her dad died, gives her no happiness, yells at her when she's too slow serving her, gets her blood-related daughters to abuse Cinderella as well, manipulates her emotions by saying she can go to the ball when she had zero intention of giving Cinderella a chance to go to the ball, only gives her rags and old, torn clothes to wear, and locks her in the attic so she has no chance of having the prince find out that she is the one with the glass slipper. Very cruel!

Siamese Cats - Lady and the Tramp

Tabuu - Super Smash Bros. Brawl

Pinhead - Hellraiser

Pinhead is the main antagonist of the Hellraiser franchise. Also known as the Hell Priest, he is one of the leaders of the Cenobites and inhabits an extra-dimensional realm known as the Labyrinth. The Cenobites can be summoned through puzzle boxes such as the Lament Configuration.

He's totally devoted to the art of torture. And he'll tear your soul apart.

Negan - The Walking Dead

Negan is a fictional character from the comic book series The Walking Dead and is portrayed by Jeffrey Dean Morgan in the American television series of the same name. He is introduced as the ruthless leader of a group called the Saviors. Negan becomes a major antagonist in both the comic and television... read more

I can't wait for Rick and what's left of his group to kill him.

The Evil Queen - Snow White and the Seven Dwarfs

The Djinn - Wishmaster

Cruella de Vil - 101 Dalmatians

Cruella de Vil is a fictional character who appeared in Dodie Smith's 1956 novel The Hundred and One Dalmatians. She is the main antagonist in Disney's animated films One Hundred and One Dalmatians and 101 Dalmatians II: Patch's London Adventure, as well as the live-action films 101 Dalmatians and 102... read more

She doesn't care about killing puppies. She wants her stupid fur coats. She even tries to steal her "friend" Anita's puppies, even when they told her they aren't interested in her offer.
She also abuses her henchmen when things go wrong, even when it's because of her that it went wrong.

Her name fits her perfectly.

Michael Myers - Halloween

Michael Myers is a character from the Halloween series of slasher films. He first appears in John Carpenter's 1978 film Halloween as a young boy who murders his older sister, then returns fifteen years later to kill again. In October 2018, a direct sequel to the original film was released, disregarding... read more

Gogo Yubari - Kill Bill

Gogo Yubari is a character in Quentin Tarantino's two-part film Kill Bill. She is portrayed by Chiaki Kuriyama. Gogo serves as the sadistic and deadly schoolgirl bodyguard of O-Ren Ishii, one of the members of the Deadly Viper Assassination Squad.

"Gogo may be young, but what she lacks in age, she makes up for in madness." - The Bride