The creepiest smiles in movies

Let’s start with a gimme. Pennywise may not be the oldest ghoul on the block, but the grin he slaps across his face when he tastes a child's “delicious fear” can make your spine crumple into a pretzel. Tim Curry may have been the first to bring the other killer clown from outer space off the pages of Stephen King’s novel, but Bill Skarsgård’s icy stare mixed with that killer smile make Pennywise that much scarier. He contorts his face behind all that makeup and a giant prosthetic head just before he bites into another one of Derry, Maine’s children, to create a true atmosphere of dread and fear that lingers long after he’s left the screen.

The first Omen film in 1976 may be an overrated classic, but the ending is worth ignoring its minor flaws. The story of little Damien, who may or may not be the anti-Christ, is confirmed in the film's final frames with a simple turn of his head. During the final scene, we’re treated to the funeral of Damien’s foster parents. The camera zooms in on Damien just as he turns his head towards the lens and breaks the fourth wall by shooting a childish grin to the audience that’s just grim. Director Richard Donner reportedly got child actor Harvey Spencer Stephens to smile for the camera by telling him NOT to smile, which makes the scene even creepier since his grin is so genuine and innocent.

Imagine sitting through a movie that’s one long, silent creeper. This classic 1928 silent drama based on Victor Hugo’s novel tells the story of a 17th-century nobleman named Gwynplaine who has a permanent smile carved across his face. The smile was made by a surgeon who mutilated children to force them to grow into a certain look on the orders of an English king. The movie’s central story is kind of an Elephant Man meets The Killing Joke, with a grim love story as Gwynplaine tries to live a normal life despite his disfigurement, but his permanent grin forces him into a life on the road in a traveling freak show. Gwynplaine may not be trying to creep people out, but the story is so heart-wrenching that it forces you to put yourself in his place, simultaneously producing feelings of dread and sympathy. Conrad Veidt’s portrayal of the constantly smiling man is so memorable that it inspired some of pop culture’s most famous grinning villains, like The Joker.

DC Comics’ most famous villain has inspired some great performances from the likes of Jack Nicholson, Cesar Romero, and Mark Hamill, but the creepiest take on Batman’s not-so-better half goes to the Oscar-winning performance by Heath Ledger in the second of director Christopher Nolan’s Batman trilogy. Just like poor Gwynplaine in The Man Who Laughs, this Joker has a scarred grin carved into the sides of his mouth, and the scariest part of it is that he seems to have a million different stories for how he got them. Once again, the possibilities of a scenario that can turn a human being into a psychopath who plays with human lives the way a kid plays with Legos are way more horrifying when the script leaves it up to an audience’s interpretation.

Creepy smiles usually crop up in the middle or towards the end of heavy movies, but Alex DeLarge’s grin is the very first thing on camera, and it tells you everything you need to know about this “horror show” of a human being. Director Stanley Kubrick’s take on Anthony Burgess’ most famous novel about a gang of British teens with a penchant for violence whose leader is forced into rehabilitation by a dystopian system that has no idea how to contain people like him is as grim and dark as a Kubrick film can get, and that’s pretty grim. Alex, played brilliantly by Malcolm McDowell, is introduced to his audience with a long, slow, simple zoom that zeroes in on that evil grin, and he never loses his gaze on the lens or the audience, for that matter.

Alfred Hitchcock’s most successful and famous horror film ends with a creepy smile from its main antagonist that makes for a perfect ending. Norman Bates, played by Anthony Perkins, spends the majority of the film as a nebbish, unassuming motel owner who cowers under the hateful eye of his murderous mother. Then, at the end, we learn that both of these powers are actually one person. He has a split personality, one of them is his knife-wielding mother, who believes she’s protecting his little boy. Norman tries to reason with him/herself as the camera pulls in on his face. He grins for the camera giving the audience one last reason to gasp for a breath.

This Japanese cult classic about teenagers being forced to compete in a real-life death match builds enough tension with its horrific premise. Mitsuko Souma, played by Stephanie Komure, turns out not only to be one of the teenage culling game’s deadliest killers but also seems to get a lot of pleasure out of it. The smile that crawls across her face is one of the movie's most iconic moments. Megumi, played by Sayaka Ikeda, finds herself cornered in a dark shack. When the flashlight turns on her supposed friend’s face, Mitsuko immediately begins to smile, revealing her true violent side in a very startling way. Even if she doesn’t pounce immediately, the audience knows that an evil demon hides behind that smile and may even enjoy being forced to hunt and kill her classmates in such jarring ways.

Donnie, played by Jake Gyllenhaal, is a disturbed kid who seems to be suffering from some kind of psychosis that makes him believe he’s seeing a giant, sinister-looking bunny named Frank. Donnie sees a lot of other things that may or may not be there. We don’t really know if Donnie is the good or bad guy in this very complex and unique story of teen angst and the properties of time travel. Then when things seem like they couldn’t get more bewildering, Donnie starts seeing trails of his family’s future movements in their home as if he can see their souls guiding them, and he smiles. Is he amused? Is he so horrified by all of the visions he sees that all he can do is smile at his insanity? The possibilities that crawl across his face are harrowing and horrifying.

The Insidious films are one of the few horror franchises that manage to create genuine dread and scare even after they’ve reached the fourth sequel mark. The second one produces some of the biggest screams with this scene of a ghostly family forced to live through a hellish afterlife over and over and over again. When Josh Lambert, played by Patrick Wilson, enters “The Further,” he comes across ghosts of a family trapped in the dark dimension. The “Doll Girl” spirit is being forced to relive a hellish moment where she murders her entire family on an infinite, ethereal loop. Apparently, it’s been happening for so long that the family has learned to find the whole situation entertaining. The smiles on their faces are even more jarring under the glowing green light of the scene that plays out their ghoulish punishment.

Bond villains are known for cracking a smile when they think they’ve got one up on the super spy or are on the verge of dispatching him to that great martini bar in the sky. In the brilliant Skyfall,  Raoul Silva, played by Javier Bardem, easily has the creepiest smile of them all thanks to a grisly scene that you’ll never be able to forget. The evil Bond villain is interrogated by M (Dame Judi Dench) when Silva one-ups her by removing his false teeth and showing her his disfigured teeth and jaw. The grin Silva plasters on his face to M’s horrified reaction personifies the evil coursing through his veins, making him seem even more villainous.

The cult of this killer clown broke the box office with Terrifier 2, but it’s only fair to pay homage to Art’s first starring feature. The brutal horror film series features the constantly smiling clown, played by David Howard Thornton, who molds gory murders the way that sculptors mold hunks of clay into works of art. Clowns have been scary for a long time, but Art’s black, grinning chompers feel like something out of a nightmare we didn’t know we could have. His infamous story and chilling face have made him a viral meme and even scarier because it feels like he could leap off the screen and into our realm at any moment.

One creepy smile in a movie is hard enough to take. Smile forced you to endure a whole movie that’s full of them. The smiles in this creative horror hit indicate that a person has been taken over by a grinning demon who delivers the creepiest smile of them all when it’s in its true form. The scariest part is they can happen at any moment and to anyone. The smiles also indicate that some kind of tragic death is soon to follow, and no one is safe. The smiles in “Smile” even found their way off the big screen when the studio paid actors to sit in the stands behind home plate during the World Series so they could deliver big, creepy smiles to the people watching at home.