The earliest skyscraper on record won the Derby. It was a racehorse.

Etymologist Barry Popik quotes an Oxford English Dictionary citation from the Racing Calendar of 1788: "Mr. Dutton named the D. of Bedford's c. Skyscraper, by Highflyer." The colt, foaled in 1786, was a son of a stallion called Highflyer. Wikipedia says his name is thought to refer to his height. He won the Epsom Derby in 1789, the date Etymonline gives for this sense.

After that, the word drifted to almost anything that reached unusually high. Etymonline lists a light sail at the very top of a mast in 1794, a high-flying bird in 1840, and a very tall man in 1857. Popik adds an 1857 slang dictionary line aimed at a lanky person: "I say, old sky-scraper, is it cold up there?" In an 1800 letter, Walter Scott wrote of swaggering in a "cock'd skyscraper," and Wikipedia lists tall hats among the word's senses. In 1866 the New York Herald used "skyscrapers" for high fly balls.

Buildings came late. The earliest building uses Popik gives are from 1883. A February 1883 Chicago Daily Tribune article was headed "OUR SKY-SCRAPERS" and discussed tall buildings in New York. That June, J. Moser in American Architect and Building News proposed topping a capitol dome with "a gigantic 'sky-scraper'." Etymonline lists that year's sense as an ornament on top of a building.

The modern sense settled in Chicago at the end of the decade. Etymonline dates "very tall urban building" to 1888, in a Chicago context. In December 1888 the Inter-Ocean boasted that "the 'sky-scrapers' of Chicago outrival anything of their kind in the world."

Chicago had good reason to boast. After the 1871 fire the city rebuilt and banned new wooden construction. The ten-story Home Insurance Building, designed by William Le Baron Jenney and finished in the mid-1880s, is often called the first skyscraper. Its metal frame carried the floors and helped support the outer walls, though masonry still bore some of the load. By 1893, Wikipedia says, Chicago had built 12 skyscrapers of 16 to 20 stories.

Other languages copied the image. Etymonline gives French gratte-ciel, "scrape sky," and German Wolkenkratzer, "cloud scraper." Only the horse has been forgotten.