Born in 1783, Washington Irving is thought to be the first American to earn his living entirely by writing. As the last of 11 children, Irving was frail and pampered, and allowed to indulge his interests in stories and the theater in a way his siblings had not been. By age 19, he was contributing pseudonymous letters to the Morning Chronicle, a newspaper edited by his brother in New York City. These were light and satirical, and well-written enough to attract some attention from readers, notably Aaron Burr. Due to his ill health, Irving regularly visited the Hudson Valley, an area that would later serve as the setting for his most famous works. His condition also prompted his first extended visit to Europe from 1804–1806. 

When Irving returned, he passed the bar exam, though not impressively. Once again he wrote, this time for the literary magazine Salmagundi. He wrote more satire about New York City society under several pseudonyms, again drawing praise and admiration for his work in and away from New York. It was in this context that Irving referred to New York City as "Gotham" for the first time, coining the term. When his fiancée died, he completed his first full-length work, A History of New-York from the Beginning of the World to the End of the Dutch Dynasty, by Diedrich Knickerbocker. This was the first instance of Irving's use of the pen name Knickerbocker, one that would show up in both "Rip Van Winkle" and "The Legend of Sleepy Hollow."

In 1815 he moved to Europe, where he would live until 1832. This was his most productive period of literary creation. In 1819, he began serially publishing The Sketch Book of Geoffrey Crayon, Gent. Most of the short stories are about England, in the fanciful vein that Irving was by then well known for. Two of the stories, however, were "Rip Van Winkle" and "The Legend of Sleepy Hollow," both re-imaginings of German folktales set in upstate New York. These would prove to be Irving's literary legacy, but were written relatively early in his career. He would go on to write and publish five more books during his time in Europe, and when he returned to the United States, three more books would follow. Aside from four years as U.S. minister to Spain, he would spend the rest of his life in Tarrytown, NY, notably near the village of Sleepy Hollow. His estate, Sunnyside, was known as a place where writers and thinkers gathered to exchange ideas and enjoy a good conversation. Washington Irving died in 1859.