Irving was born and raised in New York City, the youngest of eleven children of a prosperous merchant family. A dreamy and ineffectual student, he apprenticed himself in a law office rather than follow his elder brothers to nearby Columbia College. In his free time, he read avidly and wandered when he could in the misty, rolling Hudson River Valley, an area steeped in local folklore and legend that would serve as an inspiration for his later writings.
As a nineteen-year-old, Irving began contributing satirical letters under the pseudonym Jonathan Oldstyle to a newspaper owned by his brother Peter. His first book, Salmagundi; or, The Whim-Whams and Opinions of Launcelot Langstaff, Esq., and Others (1807-08), was a collaboration with another brother, William, and their friend James Kirke Paulding. This highly popular collection of short pieces poked fun at the political, social, and cultural life of the city. Irving enjoyed a second success in 1809 with A History of New York, from the Beginning of the World to the End of the Dutch Dynasty, a comical, deliberately inaccurate account of New York's Dutch colonization narrated by the fictitious Diedrich Knickerbocker, a fusty, colorful Dutch-American. His carefree social life and literary successes were shadowed at this time, however, by the death of his fiancee, Matilda Hoffmann, and for the next several years he floundered, wavering between a legal, mercantile, and editorial career.
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