The Season of the Creepy Smile Is Upon Us

Back in the Age of Sail, pirates liked to design their own flags. Often, they presented solid black backgrounds with white skulls sewed onto them. The purpose was simple: They were scary. While it seems obvious that the skulls represented death, something else was at work, too. There is something uncanny about a grinning skull.

Research conducted by the University of Minnesota in 2017 indicated that big, toothy, V-shaped grins are considered the creepiest. This big smile is the closest approximation to the horrible rictus on your typical skull.

The grimace on the skull—the wide display of teeth, the blank and expressionless eyeholes—evokes what psychologists call the “uncanny valley.” This refers to “the dramatic dip in the likability of inanimate objects as they become increasingly more human-like.” A blanched skull does not look like a living human face, but its grin, blank eyes, and the ghastly nose openings summon an eerie human-ness. As Freud posited long ago, the “uncanny” is something that is not a live person but yet resembles a person. He used “wax-work figures, artificial dolls and automatons” as examples.

In the 1928 classic film The Man Who Smiles, gaunt German actor Conrad Veidt played Gwynplaine, a man whom “Gypsies” had operated on as a youth, giving him a surgical smile for a life. The makeup effect, created by future Frankenstein and The Wolf Man makeup artist Jack Pierce, is horrifying. Though the film is not a horror movie, looking at still images of Gwynplaine still sends chills up one’s spine. Supposedly, the comic character Joker was based on this screen character.

This month, we get the latest installment of grimace-horror in the sequel to Smile, aptly titled Smile 2. The first film was highly successful, telling the story of a curse wherein victims effect a big, gaudy smile before killing themselves. As director Parker Finn explained, what drew him to the idea was the “dead gaze that’s a total mismatch for the smile.” He understood the power of “a human face that pushes you into the uncanny.”

Uncanny smiles always abound during the Halloween season. Besides regularly scheduled smiley horrors—i.e. the layered, fanged smirk of Pennywise the Clown in the recent It films (both released during this time of year) and other clown-fear movies, we might also think about what’s on our porches.

The glowing, smiling Jack O’ Lantern has its origins in Ireland. According to the Carnegie Museum of Natural History, an irrepressible cad named Stingy Jack tricked the Devil “into changing his form, then trapping him in his transfigured state. Jack then offered the Devil out of the deal in exchange for not taking his soul for a long time. Some longer versions of the story have the Devil being tricked 3 or 4 different times.”

When Jack died, neither God nor the Devil wanted him. He was cursed to walk the land “for all eternity with nothing but an ember given to him by the Devil to light his way.”

In combination with the Gaelic celebration of Samhain, people started putting candles or glowing coals in gourds in Jack’s honor, and then go from house to house asking for food and drink. The pumpkin, first cultivated by indigenous peoples in America and later shipped abroad, ultimately became the gourd-of-choice for Stingy Jack. The term evolved into Jack of the Lantern, and ultimately, the now familiar Jack O’ Lantern.

Suitable for the Samhain-inspired ghostly holiday of Halloween, the Jack O’ Lantern eventually acquired its nearly universal expression: the big toothy grin. It’s the same evil grin that pirates once used to inspire their quarry to hand over their loot.