Top 10 Fictional Characters with the Creepiest Smile

The Top Ten
1 Jeff The Killer - Creepypasta Jeff the Killer is a creepypasta usually accompanied by a picture of a white face looking in to the camera smiling in an unsettling manner. The creepypasta is also usually accompanied by the term "Go to sleep".
2 Hannibal Lecter - Silence of The Lambs Dr. Hannibal Lecter is a character in a series of suspense novels by Thomas Harris. Lecter was introduced in the 1981 thriller novel Red Dragon as a forensic psychiatrist and cannibalistic serial killer.
3 The Joker - Batman The Joker is a fictional super villain created by Bill Finger, Bob Kane, and Jerry Robinson who first appeared in the debut issue of the comic book Batman (April 25, 1940) published by DC Comics. Credit for the Joker's creation is disputed; Kane and Robinson claimed responsibility for the Joker's design, while acknowledging Finger's writing contribution. Although the Joker was planned to be killed... read more

"Lets put a smile on that face".

4 Alex - A Clockwork Orange
5 The Smiling Dog - Creepypasta
6 The Coachman - Pinnocchio
7 Minnie Mouse - Disney Minerva "Minnie" Mouse is a cartoon character created by Ub Iwerks and Walt Disney. She was first drawn by Iwerks in 1928, as was Mickey Mouse. Her former voice actor Russi Taylor (1944 - 2019) voiced her for 30 years & also married Wayne Allwine (1947 - 2009), the former voice of Mickey Mouse. Minnie Mouse is currently being voiced by Kaitlyn Robrock
8 Tomura Shigaraki - My Hero Academia
9 Princess Luna - My Little Pony
10 Apple Bloom - My Little Pony: Friendship is Magic Apple Bloom is a female school-age Earth pony and a member of the Apple family. She appears as a secondary character in the animated children's television series, My Little Pony: Friendship is Magic. Apple Bloom is the younger sister of Applejack and Big McIntosh, as well as the granddaughter of Granny Smith. She is one of the founding members of the Cutie Mark Crusaders, a club/"secret" society dedicated... read more

The Newcomers

? Darla Dimple - Cats Don't Dance Darleen "Darla" Dimple (also known as Darla Dimple) is the main antagonist of Warner Brothers' 1997 animated film Cats Don't Dance.
The Contenders
11 Gollum - The Lord of The Rings Gollum is a fictional character from J. R. R. Tolkien's legendarium. He was introduced in the 1937 children's fantasy novel The Hobbit, and became an important supporting character in its sequel, The Lord of the Rings. In Peter Jackson's Lord of the Rings and Hobbit trilogies, he is portrayed via motion capture by Andy Serkis.

He's creepy, and his voice is irritating.

12 Scootaloo - My Little Pony
13 Shiro - Deadman Wonderland Shiro is a mysterious and enigmatic character in the anime and manga series Deadman Wonderland. Recognizable by her all-white attire and childlike demeanor, she harbors dark secrets and has a deep connection to the protagonist, Ganta Igarashi. Her dual nature of innocent appearance and violent tendencies adds a sense of unpredictability to the story. Shiro serves as both an ally and an enigma that... read more
14 The Grinch - How the Grinch Stole Christmas The Grinch is a fictional character created by Dr. Seuss. He first appeared as the main character of the 1957 Christmas story How the Grinch Stole Christmas! In 1982, he appeared in a crossover with the Cat in the Hat, with the 25 minute episode 'The Grinch Grinches the Cat in the Hat' and in 2018 will get another movie after the 2000 movie: 'How the Grinch Stole Christmas', with Jim Carrey playing... read more
15 Sweetie Belle - My Little Pony
16 Rainbow Dash - My Little Pony Rainbow Dash is a female Pegasus pony from the 2010 kids' show, My Little Pony: Friendship is Magic. She represents the element of loyalty and is one of the six main characters on the show.

Her name is composed of "Rainbow" (referring to the color of her mane, the sonic rainboom she performed, and her previous occupation as a weather pony) and "Dash" (referring to her love for flying and her... read more
17 Twilight Sparkle - My Little Pony Twilight Sparkle is the primary main character of My Little Pony Friendship is Magic. She is a female unicorn pony who transforms into an Alicorn and becomes a princess in Magical Mystery Cure.
18 Norman Bates - Psycho Norman Bates is a character created by writer Robert Bloch as the main character in his novel Psycho, and portrayed by Anthony Perkins as the primary antagonist of the 1960 film of the same name directed by Alfred Hitchcock and its sequels.
19 Lord Voldemort - Harry Potter Lord Voldemort is a fictional character and the central main antagonist in J. K. Rowling's series of Harry Potter novels. Voldemort first appeared in Harry Potter and the Philosopher's Stone, which was released in 1997.
20 Rarity - My Little Pony Rarity is a female Unicorn pony from the 2010 Animated Television Series My Little Pony:Friendship is Magic. She is the element of Generosity and her main passion is fashion.
21 Pennywise - It It (sometimes capitalized as IT), more commonly known as Pennywise the Dancing Clown, is the titular main antagonist of the novel, its 2017 film adaptation and the 1990 TV adaptation. It was portrayed to be a shapeshifting and malevolent entity millions (possibly billions) of years old, and with no exact gender or solid identity; thus why it is called "IT"... read more
22 Diamond Tiara - My Little Pony Diamond Tiara is a female school-age Earth pony and minor antagonist who first appears in Call of the Cutie. She and Silver Spoon are classmates of the Cutie Mark Crusaders.
23 Smiler - The Emoji Movie
24 Envy - Fullmetal Alchemist/Brotherhood
25 Happy Mask Salesman - The Legend of Zelda: Majora's Mask
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