“There’s a fascination frantic / In a ruin that’s romantic” – Gilbert and Sullivan, in The Mikado.

Ruins have for several centuries been objects of literary and artistic veneration, reminders of real and imaginary catastrophe, images of historical hubris and souvenirs from dashed futures. Central to the history of Western aesthetics, ruins are also symbols of the perils of Romantic melancholy, of picturesque sentiment and pure kitsch. From Denis Diderot’s meditations on the paintings of Hubert Robert, through Romantic poetry and “The Fall of the House of Usher” to J. G. Ballard’s post-industrial sublime, writing on ruins has been an ambiguous undertaking; the enthusiast of decay has one eye on the past, the other on thrilling visions of a collapse still to come. Ruins are the poetic embodiment of futurism and regret.

Hypnerotomachia Poliphili by Francesco Colonna

The taste for ruins is a decidedly modern pleasure. There are few (if any) classical or medieval instances of aesthetic excitement about tumbling masonry and overgrown temples, and even in Renaissance painting the ruin serves mostly as a backdrop or support: the sort of thing St. Sebastian leans on in his last moments. Among the earliest examples of the “ruin lust” that would later dominate European art and literature is this textual monstrosity from 1499, a dream narrative in which the Poliphilo of the title searches for his lost love in a landscape dotted with architectural grotesques, fragments from classical statues and buildings, and enigmatic or partial inscriptions. The engravings that accompany Colonna’s bizarre story – which is itself a sort of ruin, composed in a curious amalgam of Latin, Greek and Italian dialects – predate the more celebrated ruins of Piranesi by two and a half centuries.

After London by Richard Jefferies

The obverse of Victorian optimism and industry is a growing taste for the art and literature of disaster. At the end of the eighteenth century, Hubert Robert painted the Louvre in ruins after some nameless future catastrophe, and Sir John Soane commissioned the painter Joseph Gandy to depict his Bank of England in ruins a few decades later. In 1840, Thomas Babington Macaulay imagined London in ruins; an intrepid New Zealander pausing to gaze upon the wreckage of St. Paul’s Cathedral. Richard Jefferies’s post-apocalyptic novel of 1885 is the logical summation of the nineteenth century’s fears and covert desires regarding urban ruin, a direct precursor of Hollywood’s long romance with futuristic disaster and decay, and a proto-environmentalist vision to match our contemporary imaginings of a post-human future. Civilization has come to an end, and England reverted to medieval ways of life, while farmland turns to wilderness, a vast lake covers much of the country, and London itself is once more a marsh: “For this marvelous city, of which such legends are related, was after all only of brick, and when the ivy grew over and trees and shrubs sprang up, and, lastly, the waters underneath burst in, the huge metropolis was soon overthrown.”

The World My Wilderness by Rose Macaulay

Macaulay’s classic study of European ruin aesthetics, Pleasure of Ruins (1953), is a sedulous history of several centuries of artists’ and writers’ attraction to decay. It’s also a sprightly and eccentric piece of writing; Macaulay had ruin lust in the blood (she was grand-niece of Thomas Babington Macaulay) and was not above sniffily dismissing certain kitsch artifacts of a tradition she adored. Pleasure of Ruins was partly inspired (if that’s the word) by the loss of her home and library in the Blitz – she’d lost “everything but my eyes to weep with”, she wrote in May 1941. The sight of London in ruins is the key motif too in this, Macaulay’s lesser-known fictional reflection on rubble and weeds, desolate streets and oddly elated survivors. Published in 1950, The World My Wilderness concerns middle-class adolescent siblings, Barbary and Raoul, turned feral among roofless apartments, the vacant precincts of medieval churches and cellars haunted by sinister black-marketeers. It’s in many respects a conventional novel, but Macaulay keeps veering into hymns to glittering brick dust or drifts of purple ‘bombweed’, littering her narrative with more or less blatant citations of T. S. Eliot’s "The Waste Land," refusing the solace of solid realist form.

The Arcades Project by Walter Benjamin

The fragments of this unfinished masterpiece that Benjamin amassed between 1927 and his death while fleeing the Nazis in 1940 are famously organized around the reality and metaphorical import of the Parisian shopping arcades of the previous century. These once glittering temples to commodity fetishism had fallen into disrepair, but to Benjamin, still embodied a lost vision of the future. “They are residues of a dream world”, Benjamin writes in a preparatory essay of 1935: “With the upheaval of the market economy, we begin to recognize the monuments of the bourgeoisie as ruins even before they have crumbled.” Like the Surrealists, Benjamin thought of the dated and decayed remains of the old century as ripe for utopian reuse; The Arcades Project is full of doleful images of decay – the overstuffed bourgeois interior as cabinet of moldering curiosities, the folds of ornate dresses as devices for the collection of dust – that he blasts out of the continuum of history, rescuing their strangeness and radical potential. At the same time, the incomplete book is itself a ruin: conceived as a mutable field of fragments and quotations, in its edited and published form it’s an exploded monument to its author as much as its subject.

“A Tour of the Monuments of Passaic, New Jersey” by Robert Smithson

Schooled on Eliot, Borges, Beckett and Ballard, Robert Smithson was a wry and energetic essayist: his writings of the late 1960s and early 1970s are in no sense simply adjuncts to the artworks – Spiral Jetty and Partially Buried Wood Shed are the best known – that he was making at the time. This essay, first published in Artforum in October 1967, is the smartest (also most erudite, and funniest) statement of his ruinous interests. Smithson takes a bus from the Port Authority terminal in Manhattan to the New Jersey town where he was born, and discovers on the outskirts, among the post-industrial relics, certain “monuments” that convince him he’s in the new Eternal City. Drainage pipes, pumping derricks, defunct earth diggers and an entropic sandpit: all of it amounts to what the artist calls “ruins in reverse” – a landscape being built and abandoned in the same instant. The essay has many gorgeous mock-visionary moments – Passaic, he writes, is a place “where the machines are idle and the sun has turned to glass” – and deadpan interludes: Smithson turning everything from the packaging of his Instamatic film to a children’s playground into an image of modern entropy. Like Benjamin’s book, “A Tour of the Monuments” is overexposed in the art and criticism of the last decade or two – I’ve walked the Smithson trail around Passaic myself – but the essay is still a scintillating guide to post-war ruin lust.

Stones of Aran by Tim Robinson

The Yorkshire-born artist, cartographer and essayist Tim Robinson is the Proust of Europe’s western seaboard, a writer whose extreme eloquence and eye for detail are combined with a deep sense of landscape as agglomeration of nature and culture, violent geology and the slumped remnants of futures past. Since abandoning the London art scene for the west of Ireland in the early 1970s, Robinson has written a series of fantastical and delicately researched books about the Aran Islands and the mainland region of Connemara where he now lives. The two-volume Stones of Aran, published in 1986 and 1995, takes its title and inspiration from John Ruskin’s Stones of Venice (as well as art historian Adrian Stokes’s Stones of Rimini of 1934) and treats the islands as if they were crumbling Gothic cathedrals or bravura projects by some vanished land artist. Robinson is a connoisseur of fractured rock strata, scattered boulders, tumbledown cottages, Famine graves and concrete relics of abandoned industry. But his is not a Romantic or nostalgic ruin lust: Robinson is also a mathematician, and even (or especially) at his most poetic, he brings a keenly abstracted understanding of complex erosional processes and unravelling economic structures to his study of places too often swamped by sentiment.

The Rings of Saturn by W. G. Sebald

Sebald’s melancholy volumes are littered with ruins, and with knowing reminders of the literary and artistic history of ruin appreciation. In On the Natural History of Destruction, he reflects on the ruin-fixated fiction and cinema that emerged in Germany after the Second World War. In the opening pages of Austerlitz, his narrator drifts lugubriously from the faded grandeur of nineteenth-century railway stations, through the grim interiors of a Belgian fortress used by the Nazis as a staging post for the death camps, to the gloomy corridors of the Palais de Justice in Brussels. Even modern buildings such as the Bibliothèque Nationale in Paris seem in Austerlitz to predict their own ruin. But The Rings of Saturn is Sebald’s most resonant fugue on the theme of decay. His semi-fictional stand-in trudges the marshes of East Anglia and uncovers dilapidated mansions, Cold-War-era testing grounds and the spot on Dunwich beach where a church and its graveyard slipped over the cliff edge in 1919. Even the fish (“or what feigned to be fish”) he’s served in a run-down hotel collapses at the touch of a fork, “a sorry wreck”. It’s an example of Sebald’s comic insight into his own taste for ruins, and a clue to the absurdity of ruin lust in general – at its logical extreme, the ruinous gaze turns everything it touches into a memento mori.

Brian Dillon’s anthology Ruins is published by MIT Press/Whitechapel