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Hieronymous Bosch, The Garden of Earthly Delights (detail of hell panel), c. 1490-1500, Museo del Prado, Madrid

Bosch is one of the most enigmatic painters in Western art history; the meanings of his pictures, and the often-bizarre imagery he employed, are still hotly debated by scholars to this day. His monumental triptych in the Prado is perhaps his best-known work and certainly contains the most striking depiction what was clearly one of his favourite subjects – hell. The other panels that make up this altarpiece describe Adam and Eve’s expulsion from the Garden of Eden and the titular Garden of Earthly delights with all its temptations. This, the final panel, shows us what horrors await fallen man in the next life. Depictions of hell were commonplace in both the Northern and Italian Renaissance works, but no other artist rendered the subject with quite such disturbing inventiveness as Bosch; the twisted creatures and wicked punishments meted out in this painting are truly something from a nightmare.

Louis-François Roubiliac, Monument for Sir Joseph and Lady Elizabeth Nightingale, 1761, Westminster Abbey, London

Surely the most dramatic and terrifying funerary sculpture carved in England, the Nightingale monument in Westminster Abbey has been unsettling churchgoers since 1761. The monument was carved by one of greatest mid-18th century émigré sculptors in England, Louis-François Roubiliac. The sculpture depicts Sir Joseph vainly trying to protect his dying wife Elizabeth from Death’s fatal dart. The figure of Death is shown bursting through the doors of a vault below and takes the form of a skeleton draped in a hooded robe. This sculpture takes on a certain poignancy when we learn that Elizabeth had died in childbirth in 1731, 21 years before her husband, who survived until 1752. Pathos aside, the sculpture has a track record of scaring people – a popular tale goes that it proved so terrifying to a burglar, who unexpectedly encountered it in the night, that he downed his crowbar and fled the scene.

Henry Fuseli, The Nightmare, 1781, Detroit Institute of Arts, Michigan

This painting by the Swiss / British painter Henry Fuseli, is a defining image of the Romantic period in art and literature. More specifically, it is closely aligned with the aspect of the movement that saw a revival of gothic architecture as well as gothic novels like Horace Walpole’s The Castle of Otranto (1764) and Mary Shelley’s Frankenstein, published early in the following century. Set against this backdrop, Fuseli started exploring dark themes in his work, often taking violent or supernatural passages from Shakespeare and classical mythology as his subjects. This painting, however, is set apart from this category as it has no literary basis and instead takes its cues from deeper psychological and folkloric anxieties. The woman in the painting is shown fast asleep, while a squatting incubus sits upon her chest and a spectral horse peers through the curtain behind. It is unclear whether the painting is supposed to depict a supernatural event – the visitation of a demon – or whether it is an evocation of the woman’s internalised nightmare. Either way, it is an image that remains as popular, and as troubling, as when it was first exhibited to a morbidly fascinated public at the 1782 Royal Academy Summer Exhibition.

Francisco Goya, Wtiches’ Sabbath, 1797-98, Museo Lázaro Galdiano, Madrid

For an artist whose best works are known as the Black Paintings, it is unsurprising that much of Goya’s oeuvre is characterised by dark subject matter. Whether he was depicting the Peninsular War in his The Disasters of War etchings or the supernatural, Goya was always willing to confront the gruesome issue at hand head-on. This painting, which dates from before the Disasters of War and Black Paintings, was commissioned by the Duchess of Osuna, an enlightenment figure who, along with her husband, was a major patron of the arts in Madrid. The Witches’ Sabbath is one of six paintings of a similar subject commissioned by the Duchess from Goya. It is thought that these paintings were intended as a satirical and critical commentary on Spanish peasant superstitions at the time, stoked by the apparently medieval fearmongering of the Catholic church. Despite painting’s perhaps cynical aims, the image itself pulls no punches. The canvas depicts Satan, in the form of a horned goat, standing amidst a coven of witches who in turn offer him babies, some dying, others dead.

John Atkinson Grimshaw, In the Gloaming, 1878, The Mercer Art Gallery, Harrogate

John Atkinson Grimshaw was a Leeds-based painter, who worked prolifically in the second half of the 19th century. The vast majority of works are lyrical depictions of Victorian townscapes at night, dusk or dawn. He is therefore known for his mastery of lighting effects and his ability to manipulate them to create a heavily atmospheric mood. Although mostly he mostly lived in Leeds, he did have a studio in Chelsea near that of James McNeill Whistler, who stated that ‘I considered myself the inventor of nocturnes until I saw Grimmy’s moonlit pictures.’ A notable portion of his oeuvre was given to depicting old houses at night or twilight. Many of these show his home, Knostrop Hall in Leeds, while others, like this picture, appear to be inventions on Grimshaw’s part and accordingly have titles such as In the Gloaming or The Olde Grange at Sunset etc. Although there is nothing explicitly paranormal about this picture, this work, and many like it, have a distinct eeriness, and perfectly express the late autumnal atmosphere of Halloween.