The devil comes out to play at Halloween – but people haven’t always viewed hell and its creatures as good clean fun. When artists 600 years ago painted their satanic scarefests, they weren’t just trying to entertain. Medieval Europeans believed in the existence of hell as a physical place. Paintings in parish churches across Britain depicted the damned being led into hell by clawed, scaly cloven-footed demons. In Flanders and Germany, painters competed to make the legions of the devil and the horrors of hell seem utterly real. That’s how the world’s scariest satanic works of art were created. Gothic paintings have a belief in the demonic world that gets deep under your flesh. Here are four devilish masterpieces that survive to thrill us from a lost age of fear – and one wicked modern update. Matthias Grünewald – The Temptation of Saint Anthony A hermit is menaced by creatures of surpassing strangeness. A half human, half bird creature comes at him with a tree branch: one with a face like a pickled sea creature plucks at his arm with its warty claw. Other demons have antlers and rabbit teeth, or a wild dog’s face with horns. The early Christian Father Anthony was said to have been tested by devilish “temptations” in the Egyptian desert. What is the nature of this testing, as imagined by Grünewald? It’s not sex or greed that torments him but imagination itself. These are the creatures at the edge of our minds, assembled from bits and pieces of real animals and animated by sheer terror. Modern artists, including the surrealist Max Ernst who adapted Grünewald’s bird creature into his own avian demon Loplop, have recognised the authority of this particular nightmare. The evocation of a mind crumbling into chaos would also have been recognised by patients in the monastic hospital for which Grünewald painted this altarpiece. Plagued by the poisonous disease ergotism, they would have seen in it a mirror of their fever dreams. The figure at the lower left of the painting with a body covered in red pustules probably depicts one of these patients, lying in a sweat, seeing these horrors. The Temptation of Christ, King’s College Chapel, Cambridge In this early 16th-century stained glass window, Jesus speaks to an old bearded man, cowled and robed, whom he has met in a green woodland. This scene painted into glass is based on a print by a German engraver known only as the “Master L Cz”. In his Temptation of Christ, the devil is a monstrous being with clawed scaly hen’s feet, beaked faces protruding from his bony knees, and a wild root emerging from an animal face on his groin, as well as horns on his head. In King’s College, however, those grisly details have been replaced by uncanny, everyday evil. The Devil presents himself as an ordinary, perhaps even wise, man you might meet on any walk in the woods. This may be a genuinely English folk image that sees greater fear in an articulate, human-seeming duplicitous Satan than an exotic horned beast. One person who may have pondered that was the King’s College don and author of great ghost stories MR James, who must have seen this window often. Dirk Bouts – The Fall of the Damned Pale naked bodies plummet into the pit carried downwards by flying demons, through a midnight blue sky that changes to pink as it is lit by infernal fires. The devils in Bouts’s scene take multiple hybrid forms as they buzz around in an evil swarm. One looks like a pterodactyl, another has an absurdly balloon-like body, while others have bat wings. One stands on a rocky precipice gleefully throwing a naked sinner into the depths. Sinners who have already fallen are beaten by a demon with yellow eyes for nipples, or carried aloft by a sprite with a boar’s head, or eaten alive by Satanic serpents. This was painted as a warning: do good and go to church or you may find yourself here. It comes from a triptych – a painting in three panels – that also included an opposite scene of blessed souls walking serenely into paradise. In modern times, The Fall of the Damned has been separated from its consoling, and far less famous, opposite scene of Heaven, to hang alone as a mysterious image of depravity. It has something decadent about it, as if it was created by a tortured modern artist rather than a medieval artisan. It often appears on book covers like my copy of The Monk by Matthew Lewis – haunting the gothic imagination still, a hell of wickedly perverse imagination. Luca Signorelli – The Preaching of the Antichrist There was a sudden howling wind on the cathedral piazza in Orvieto, Italy and plastic sheets smacked against scaffolding on its facade when I saw this fresco there. Signorelli’s Last Judgment includes scenes from the last days, as prophesied in the Book of Revelation. Here, the antichrist has his moment of power on earth, preaching to the people in a parody of Christ’s sermon on the mount. And the devil himself, a naked man with horns, is right there beside him, holding him close, whispering in his ear the honeyed evil words that will seduce and deceive the masses. So it will be, in the last days. Robert Mapplethorpe – Cock and Devil The punishment of souls in hell is given a very fleshy update in Mapplethorpe’s demonic black and white photograph. A shiny fat penis, tightly bound with black leather cords, is menaced with a pitchfork by a bronze statuette of a goat-footed devil who laughs maniacally under his horns as he approaches the meaty cock. He holds chains to bind it further in this photo that enters the imaginative realm of Bouts and Signorelli. But far from fearing this devil, Mapplethorpe flirts with hell’s pleasures. The binding of the phallus is the kind of sado-masochist thrill many of his photographs record. Here he brings his Catholic childhood and understanding of art history to bear to make those predilections explicitly satanic.