The 17 scariest works of art of all time

Oscar Wilde’s famous quip in 1889 that “life imitates art” has a ring of truth around Halloween. Those gruesome facemasks and contorted creatures that darken our doorsteps with “trick or treat” greetings are reminders of some of the most chilling and gory paintings over time. And those scenes of gothic horror, ghosts and creepy crawlies that inspire the occasion can be found in favourite masterpieces.  

Hieronymus Bosch, The Garden of Earthly Delights, 1490–1510 © Public domain

Kicking off, Hieronymus Bosch’s The Garden of Earthly Delights (1490–1510) is a misleading title in many respects as this Flemish master of surrealism produced a triptych showing hell as a consequence of earthly delights. It includes nightmarish scenes in the third right panel, which depicts a tormented hellscape. There are bleeding corpses and executioners. Half-human, half-animal creatures in bizarre, tortured poses abound. 

Hans Memling, Hell, 1485 © Public domain

The idea of hell has been the preoccupation of artists since time immemorial. In the 15th century, Hans Memling petrified churchgoers with his painting aptly titled Hell, 1485. This painting is part of a polyptych panel, Earthly Vanity and Divine Salvation (1490s) by the German-born citizen of Bruges. A wretched hybrid creature part-animal, part-human taunts the damned burning in hell. There is certainly no redemption in Memling’s painting, as a banner proclaims. Sinners burn forever in the jaws of a huge fish (just to give it that nervy edge) as the devil-like demon dances upon their suffering bodies.

Michelangelo Merisi da Caravaggio, Medusa, 1597 © Public domain

Headless corpses are a favourite subject at Halloween. Michelangelo Merisi da Caravaggio worked on the Greek myth of Medusa, a mythical woman with venomous snakes for hair, cursed by the goddess Athena and decapitated by Perseus. Medusa, 1597, is a portrait of Caravaggio’s own face, conscious, baring his teeth and dribbling blood whilst snakes writhe around his or her severed head.

Artemisia Gentileschi, Judith Slaying Holofernes, c1620 © Public domain

The terrifying act of beheading can be traced far back in the history of art. Artemisia Gentileschi’s Judith Slaying Holofernes, c1620, which portrays the biblical story of Judith, a pious, young widow from Bethulia who beheads Holofernes an Assyrian general who invades her city, is a particularly frightening example from the Baroque artist. The brutal act of revenge is portrayed in graphic detail apparently inspired by Gentileschi’s notorious rape. It is said to be one of the bloodiest depictions of this slaying, even surpassing one by Caravaggio, a friend of Artemisia’s father Orazio.

Francisco Goya, Saturn Devouring His Son, 1819–23 © Francisco de Goya y Lucientes via Wikimedia Commons

Saturn Devouring His Son by Spanish artist Francisco Goya was first painted as a mural at the artist’s farmhouse outside Madrid between 1819 and 1823 before it was transferred to canvas. The story behind this horrific image depicts the Greek myth of Titan who fears being overthrown by his son, so he devours him. The painting is part of Goya’s “Black Paintings”, reflecting his own state of mental illness during the Napoleonic Wars. The depraved, manic face of Saturn as his wide mouth gnaws on a small corpse is truly disturbing. 

Andy Warhol, Skulls, 1976 © Erik Drost via Wikimedia Commons

American artist Andy Warhol had a keen eye for the dark side. In 1962 he started his Death and Disasters series, a divergence from his brightly coloured, “pop art”, silkscreen repetitions of celebrities. He produced around seventy artworks featuring car accidents, suicides and other morbid subjects. Big Electric Chair, 1967, was inspired by a press photograph from the prison where the Rosenbergs were executed for anti-American (communist) activities. More in keeping with Halloween is his series of skulls. Skulls, 1976, comprises six canvases of the same photographic image in a vertical grid of three rows of two.

Paul Cezanne, Pyramid of Skulls, 1901 © Public domain

Warhol was not the first or last artist taken with this morbid fascination for skulls. Perhaps he had seen Pyramid of Skulls, 1901 by Post-Impressionist, Paul Cezanne who joined other artists at the time in a genre of painting termed “memento mori” (remember death)? Like Warhol, Cezanne had become increasingly fascinated by death as he approached old age.

JEAN-MICHEL BASQUIAT Untitled (head), 1983/2001 Screenprint on paper work is from the edition of 85 https://t.co/foiInaLD6x #ART #Basquiat pic.twitter.com/KGH8sMcZHd

— ArtNetto Gallery (@ArtNettoGallery) March 19, 2017

An associate of Warhol, Jean-Michel Basquiat, produced some of the most recognised skulls in art history. One of his screenprints from Untitled (Head), 1983 sold for $110.5 million in 2017. It draws on Basquiat’s Caribbean heritage with its resemblance to masks. It incorporates the inner soft tissues of the head with block colours and bright tubes streaming from the nose to mouth. Hair is drawn in squiggles as if electrified or petrified.

Girl With Death Mask (She Plays Alone), painted in 1938, is one of my favourite Frida Kahlo self portraits. Here it is situated next to the real death mask of the artist herself, which lies on the bed in which she died in her home Casa Azul in Mexico City. pic.twitter.com/rQzdeNmRBm

— Folk Horror Magpie (@folkhorrormagpi) July 2, 2021

Mexican artist and icon in her own right, Frida Kahlo can be credited with many a dystopian image of skulls to chill the bones. Girl with Death Mask (She Plays Alone) was painted in 1938 and shows herself, a small child wearing a skull mask, an unsettling juxtaposition. Renowned for her contemplation of pain and death, not least due to a disabling accident as a teenager, Kahlo produced the most surreal of paintings, of which Without Hope, 1945 triumphs. In this, Kahlo spews gore and seafood topped with a skull.

One of the most revolting depictions of skulls belongs to Jake and Dinos Chapman, a couple of brothers belonging to the YBAs (Young British Artists) of the 1980s, who were commissioned for an exhibition entitled "Memento Mori". The hideous image of maggots crawling from eye sockets in Migraine, 2004, is not so much about death but pain, the brothers explain. Certainly, it’s much to do about horror and there’s that chilling spider on the top of the skull that clinches the deal.

Odilon Redon, The Smiling Spider, 1887 © Public domain

In comparison, French Symbolist, Odilon Redon’s spider, The Smiling Spider, 1887 looks almost (not quite) cute. Odilon liked to paint spiders, his “noirs” (blacks), and this one with the smile has a row of tiny teeth and ten legs, not eight, just to spook you that bit more.

Caspar David Friedrich, The Abbey in the Oakwood, 1810 © Public domain

The sense of fright is also derived from location and what better than a gothic pile decaying in silhouette? The Abbey in the Oakwood, by the German artist Caspar David Friedrich, is a perfect example painted in Dresden in 1810, in which a church ruin stands between dead trees. The trees must have been burnt or struck by lightning, as an eerie fog emanates from the surrounding, barren landscape. It is painted in dark monotones, almost colourless, to give that particularly chilling feel.

Joseph Mallord William Turner also produced some gothic architectural drawings which evoke the haunted house or church theme. Salisbury: A Gothic Porch in a Garden, 1798, is one of a series of Salisbury views and takes the 15th century porch of the Cathedral. Pinnacles and an imposing, huge arched doorway stand ghostly white against a threatening sky.

Sir John Everett Millais, Ophelia, 1829–96 © Public domain

Central to fear is the concept of the supernatural and ghosts. The British Pre-Raphaelites did a marvellous job of this. Elizabeth Eleanor Siddal, a model for the Victorian artists, features in many of their paintings. Her pale skin, cascades of dark, auburn hair and her structural beauty lent well to the idea of steely ghosts. Ophelia by Sir John Everett Millais (1829–96), depicts Siddal as Ophelia, a character from William Shakespeare's play Hamlet, drowning. Siddal’s painting The Haunted Wood, 1856, of a woman in a dark wood reaching out to a spirit double of herself, relates to lines from her poem A Silent Wood: “Frozen like a thing of stone, I sit in thy shadow but not alone.” 

Dante Gabriel Rossetti, How They Met Themselves, 1864 © Public domain

The idea of meeting one’s doppelganger or twin (foreshadowing death) is taken up by Siddal’s husband Dante Gabriel Rossetti who painted several versions of How They Met Themselves, the most known being a watercolour in 1864.

John Everett Millais, Speak! Speak!, 1895 © Public domain

And then there is John Everett Millais’ painting Speak! Speak!, 1895, a perfect Pre-Raphaelite image for Halloween. A white spectral appears before her bereaved lover as he reaches out, urging her to speak. 

Read more: The world's most haunted forests

Read more: Art history: Why is Paul Cezanne important?

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