From Warhol's eight-hour epic Empire to Gaudí's plans for his own Hotel Attraction, the high-rise has loomed large in the artistic imagination.

  1. Andy Warhol – Empire (1964)  The most charismatic of New York skyscrapers is the solitary star of Warhol's film, which lingers with unapologetic monotony for eight hours and five minutes on the majesty of the Empire State Building. It is best viewed not as a narrative film (that would drive you mad) but as if it were a painting. As such, it is full of love for Manhattan's lofty architecture.
  2. Edward J Steichen – The Flatiron (1904) Skyscrapers were very new when Edward J Steichen took this photograph of Manhattan's Flatiron building. The wedge-shaped tower looms romantically in the evening mist, an image not so much of soaraway modernism but of the city as a place of poignant mystery and beauty.
  3. Matthew Barney – Cremaster 3 (2002) The Chrysler building is the scene of mythic happenings and strange hocus pocus in the central film from Matthew Barney's Cremaster cycle. This art-deco tower with its metallic spire is one of the most beguiling of all skyscrapers. In Barney's film, a demolition derby takes place in its lobby and a masonic ritual is going on up on the top floor. Probably pretty much what used to happen there in the old days.
  4. George Bellows – New York (1911)  By 1911, New York City was already turning into a mountainous modern wonderland with canyons and cliff faces of construction. George Bellows portrays modern city life as a drama defined by tough grandiose architecture.
  5. Georgia O'Keeffe – The Radiator Building (1927) Georgia O'Keeffe is celebrated for sensual paintings of natural forms, but here it is the city electric that lights up her imagination. The Radiator building in New York shines out excitement and promise, because the night belongs to lovers – and high-rises.
  6. Antoni Gaudí – Hotel Attraction (1908) The great Catalan architect Antoni Gaudí, whose buildings in Barcelona offer an alternative vision of modern architecture as an organic, gothic, surrealist profusion of form, dreamed of building a skyscraper in New York. Surviving drawings of the designs for his unbuilt Hotel Attraction reveal a subversive structure with the anthill eccentricity of his Sagrada Família: a tapering tower of the psyche.
  7. Ludwig Mies van der Rohe – Friedrichstrasse Skyscraper Project (1921) The darkly expressive drawings that Mies van der Rohe produced in his attempt to build a skyscraper at the heart of Weimar Berlin reveal the sublime vision at the heart of modern vertical architecture. Crystalline and authoritative, he created a geometric cathedral, an icy citadel imposing order on the city below. In fact it would be in New York that Mies van der Rohe achieved his "perfect" skyscraper: the immaculate, sleek and classical Seagram building.
  8. Alfred Stieglitz – The City of Ambition (1910) New York, New York is rising up in this evocative photograph by Stieglitz, as high-rises define the city's sense of itself as a competitive, dog-eat-dog metropolis. Yet many of his images dwell on less glamorous urban realities: immigrants arriving in steerage at the docks and the poor huddled masses dwarfed by buildings.
  9. Raymond Hood – Terminal City (1929) This never-built design for a massive new skyscraper quarter in Chicago is a vision of the modern city as a shadowed poem of towers; of glass and concrete dwarfing the people. Yet designs can be deceptive. Raymond Hood's masterpiece, the Rockefeller Centre, is the very definition of a complex that manages – paradoxically – to be both staggering in height and human in scale. Hood showed that modern urban architecture, even as it soars, can create a warmth and community on the plazas it defines.
  10. Marcel Duchamp – The Woolworth Building as a Readymade (1916) When Marcel Duchamp arrived in New York its skyline was already a colossal modern fact. The deftly ironic artist who had invented the "readymade" by fixing a bicycle wheel to a stool in 1913 promptly claimed the Woolworth building as a readymade. In fact, this skyscraper emulates medieval architecture – it has gargoyles in its lobby. Duchamp saw its true modernity behind the gothic touches. In 1917, he would create a more portable "architectural" readymade: the porcelain urinal he named Fountain.