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The Empire State Building (1930–31) is the tallest structure in New York. For 27 years its dominance was eclipsed by the World Trade Center, but the latter was destroyed in September 2001 during a terrorist attack on the city. With an 86th-floor observatory, the building receives some 3.5 million visitors each year.

Soaring 70 stories into the sky, this dramatic skyscraper, designed by Raymond Hood in 1931–3, has shallow setbacks that recede into the distance. Part of the greatness of Hood’s design is the contrast between the building’s height and surrounding Rockefeller Center.

The gleaming, stainless steel, tiered spire of the Chrysler Building adds grace to the city skyline. William Van Alen fashioned this Art Deco classic in 1928–30 as a whimsical tribute to the automobile. The building has a decorative frieze of stylized hubcaps and silver gargoyles, much like the winged radiator caps of a Chrysler car.

This 21-story, triangular-shaped building has intrigued New Yorkers since it was built by Daniel Burnham in 1902; the shape was so unusual that people took bets on whether it would topple. The secret was in the steel frame support, which was used instead of traditional heavy stone walls: a precursor of skyscrapers to come.

Architect Cass Gilbert was responsible for this flamboyant Gothic building of 1913, the tallest building in the world for two decades after it was completed. The rich terra-cotta ornamentation accentuates the structure’s steel frame, which soars to a crown 55 stories above Broadway. The small lobby boasts one of the most luxurious marble interiors in Manhattan.

Gordon Bunshaft’s 24-story Lever House, completed in 1952, was revolutionary; it was New York’s first skyscraper built in the form of a soaring glass and steel vertical slab. It began the eventual transformation of Park Avenue into an avenue of glass towers.

The first New York building by Mies van der Rohe is this landmark “glass box” with slender bands of bronze amid walls of smoked glass rising from the horizontal open plaza. The materials in the glass-walled lobby by Philip Johnson help blur the division between indoor and outdoor space. The Four Seasons Restaurant, offering American cuisine, lies within.

The 59-story Citigroup Center, built in 1978, was New York’s first Postmodern skyscraper. The rakish, triangular top never served its original purpose as a solar panel, but it did make the building instantly recognizable. An open base on four tall columns and a reflective aluminum-and-glass exterior give the building an airy quality despite its huge size.

Cesar Pelli’s Postmodern complex, comprising four tall towers around a glorious palm-filled Winter Garden, gave the city an elegant business center when it was completed in 1985. In addition, there are public spaces for concerts and special events and an outdoor plaza on the water complete with boat marina and Statue of Liberty views.

The copper roof and crown of frosted glass atop a 48-story tower by Skidmore, Owings & Merrill bring some traditional romance to a 1989 Postmodern building. There is a wraparound arcade that acts as another entrance. The building of the World Wide Plaza complex, which includes two apartment buildings and a large open plaza, transformed a decaying neighborhood.