Skyscraper construction is concerned with two kinds of height: engineering and economic. Engineering height refers to the number of stories that are structurally feasible given the limits of existing technology and engineering know-how. Economic height refers to the number of floors that will produce the highest rate of return on the money invested.

Over the century, Manhattan has been home to the world's tallest office building, and it has always possessed by far the greatest volume of skyscraper construction. In the 1880s and early 1890s, Chicago erected some of the earliest and most handsome highrises; its 22-story, 302-foot Masonic Temple held the title in 1892, when the city enacted height regulations. By 1900, five New York towers exceeded 300 feet, and in 1908, the Singer Building stretched to 612 feet. As Manhattan's development spread north, a few outstanding skyscrapers pioneered uptown sites, notably the Times Tower, Flatiron Building, and the 700-foot campanile of Metropolitan Life Insurance on Madison Square, which took the title of tallest in 1909.

Downtown's skyline regained the crown in 1913 when the Woolworth Building soared to 792 feet. It reigned until 1930 when the Manhattan Company Building climbed to 927 feet. The spire at 40 Wall Street was soon topped by the 1046-foot Chrysler Building, then by the 1250-foot Empire State Building which held the title from 1931 to 1970 when the World Trade Center twin towers reasserted downtown's vigor. Still, by the 1950s, midtown had become the country's largest central business district, ranking first in the total volume of office space; Chicago ranks second, Lower Manhattan, third. The Sears Tower in Chicago, which became the world's tallest building in 1974, was surpassed in 1996 by the Petronas Towers in Kuala Lumpur. Nevertheless, with its unparalleled number of tall buildings, New York remains the world's preeminent skyscraper metropolis.