What do David Bowie’s macabre short film for Black Star, the cover of Michael Jackson’s album Dangerous, and Guillermo Del Toro’s Hellboy all have in common? Each owes a creative debt to the medieval painter Hieronymus Bosch, whose art has enjoyed a recent resurgence in pop culture and has adorned all manner of trendy items: leggings, Doc Martens, skateboards. Metallica, Marilyn Manson, the TV show South of Hell, and popular horror franchises like Silent Hill have also riffed on Bosch’s images, specifically his depictions of hell, which have variously featured lakes of burning sulfur and rat-kings, demonic sadists, and castration via a giant razor blade.

Bosch’s vision of hell, first committed to canvas in the late-15th century, has come to be known by scholars and the public alike as the most famous scene of the underworld in Western art—first pictured in The Last Judgment and later cemented in the terrifying scenes in The Garden of Earthly Delights. Unlike the works of his contemporaries, Botticelli and Hans Memling, Bosch’s hell isn’t limited to art-history classrooms or museums. Perhaps more than any other artist of his time, including Leonardo da Vinci, Bosch’s inferno has become ingrained not only in pop culture, but also in the broader Western conception of hell as a place of torture, monstrous creatures, and never-ending suffering.

To understand how Bosch’s hell became so influential, it’s worth looking back to what spurred him to paint these images in the first place. Born Jeroen van Aken around 1450, the artist later changed his name to the more regal-sounding Hieronymus Bosch to attract patrons and distinguish himself in a family of painters. His birth coincided with the Age of Discovery, when Western Europe began its global mapping of the world, and Christianity was undergoing a movement that anticipated the Protestant Reformation. Jos Koldeweij, an art-history professor who led the Bosch Research and Conservation Project, has said these earlier reforms called for making the Christian life one’s own, rather than relying on the church’s strict interpretations. “Each individual had to confront the permanent choice between good and evil,” Koldeweij said.

In this new spirit of independence, Bosch decided to abandon the Bible’s version of hell, which emphasizes fiery punishment and destruction, and create a more fantastical underworld that more closely resembled a battlefield. He invented sword-wielding monsters with lion-heads and an androgynous birdman who vomits nothing but dice, along with scenes where women are savaged by dogs and groups of men are raped by demons. Like the unremitting Saint Augustine, Bosch believed that hell was the result of man’s ultimate sin: an attachment to the pleasures of earth. A member of a skull-and-bones religious order, the Illustrious Brotherhood of Our Blessed Lady, Bosch saw hell as a physical world eternally separated from God. The idea was to render hell as a place so unthinkably foul that people would fear God and live according to the Gospels. This follows the narrative in The Garden of Earthly Delights: Adam and Eve are in the presence of God in the left panel and, after encountering the pleasures of earth in the center, are ultimately exiled from the heavenly realm as a result of their selfishness.

It didn’t take long for other artists to recognize the distinct power of Bosch’s work. In 1562, almost 50 years after Bosch’s death, the Renaissance master Pieter Bruegel the Elder painted The Fall of the Rebel Angels, which features a battle of decapitations and monsters smeared in blood and feces. Known to his peers as “a second Bosch,” Bruegel also painted The Triumph of Death, which shows a nihilistic hell on earth and today hangs in Madrid’s Prado museum directly across from Bosch’s The Garden of Earthly Delights. Both artists had their works collected by Philip II of Spain, who became fascinated by depictions of human-animal transformations.

Today, Bosch’s representations of hell have relevance for both the religious and the secular. For Christian believers, it’s a nauseating reminder that they’ll be asked to account for the way they’ve lived and to, potentially, suffer the consequences. For the non-religious, who make up roughly 23 percent of the U.S. population according to the Pew Research Center, hell can function as a powerful metaphor for the fact that all humans are judged in life under the law. And for both groups, Bosch’s extreme portrayals of agony go even further than analogies—they reflect the horrors that humankind have committed and endured since biblical times.

On that note, Bosch certainly drew from his own life. According to Charles de Mooij, the museum director who has organized a landmark exhibition in the Netherlands to celebrate 500 years since the artist’s death, Bosch “painted as a realist.” The Last Judgment resembles a battlefield, but it’s not simply an imaginative backdrop. Bosch was born at the tail end of the Hundred Years War in which over three million people were slaughtered and Joan of Arc was burned alive; he had a profound sense of his age’s barbarity. In many ways, the hell he imagined is a crystal ball of the bloody fight between Catholics and Protestants a century later, where during the Spanish Inquisition heretics were tortured using breast rippers and knee splitters.

The lust for war in recent times is no less obscene than it was during the Middle Ages. After the carnage of World War I, surrealists such as Salvador Dalí and René Magritte helped spur a renewed interest in Bosch. These artists weren’t only drawn to his bizarre sex scenes (see Dalí’s The Great Masturbator), but they also saw him as the quintessential modern artist whose renderings of hell mirrored the suffering and deaths of millions. Modern life itself was misery: poison gas, dysentery, shell-shock, and bandaged amputees staggering through a treeless wasteland. The French philosopher Simone Weil reflected on the war’s devastation when she soberly noted, “We must prefer real hell to an imaginary paradise.”

Since the rise of photography and cinema in the 19th century, it was also possible to transmit horrifying images around the world via newspapers and television. It’s no surprise then that the savagery Bosch painted also resonated with a culture that was experiencing the horrors of Vietnam during the 1960s and ’70s—a scholarly debate played out regarding Bosch’s moralism on violence and the hippy notion of freedom through sex. His art seems less outlandish than what unfolded during the My Lai massacre: Soldiers set fire to huts and killed women and children with machine guns, while others mutilated their victims with barbed wire, poisoned food stocks, and shot cattle and dogs for sport.

Bosch’s hell also closely parallels modern forms of torture, such as those suffered by prisoners at the hands of U.S. soldiers in Iraq’s Abu Ghraib. The images that came from the prison were absurd, but real: the smiles of soldiers standing over piles of naked bodies, collared men pulled along the floor among pools of blood, a hooded figure wired to receive electric shocks. Bosch’s imagery may have been diluted for children’s books, as in Pish Posh, Said Hieronymus Bosch, but it’s more than fodder for wallpaper. It also offers a window into the evils of ISIS, who sing from the doomsday hymnal of beheadings, sex slaves, and the destruction of sacred monuments.

Beyond its visceral resonance, another reason Bosch’s hell has continued to fascinate over the centuries is that the artist himself left no paper trail explaining the rationale behind his reinvention. The lack of diaries or letters has perhaps helped keep the appeal of his dark imagery alive, encouraging new generations of artists and museum-goers to interpret him anew, and to think about how his works continue to bear on culture today. Even if the world looks different than it did in the 16th century, Bosch’s art offers a painful but necessary reminder that much still remains the same.