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James Whitcomb Riley was born on October 7, 1849 to Reuben Alexander and Elizabeth Marine Riley of Greenfield, Indiana. He was the third of six children-John Alexander, Martha Celestina, James Whitcomb, Elva May, Humboldt Alexander and Mary Elizabeth-and fondly called "Bud." His father, Reuben Riley, was a lawyer known for his oratorical skills and service as a captain in the Union Army. He would often take young Bud to the Greenfield Court House and had hopes of his son pursuing the law. James did attempt to please his father, but the inclination to read the law was weak and Reuben Riley despaired over his son's future. It was the love of acting and versifying encouraged by his mother which captured the young poet's soul. Elizabeth Marine Riley came from a family of poets. She published verses in the Reveille, a local paper, told stories and aided the neighborhood children in organizing skits for the delight of their friends. Riley adored her. He considered her his first teacher and was deeply affected by her death in 1870.

Riley's close ties to his family are evident in his correspondence and poetry. He dedicated books to his siblings-Afterwhiles (1887) to Humboldt, Pipes O' Pan at Zekesbury (1888) to John Alexander, and Green Fields and Running Brooks (1892) to Elva and Mary-and composed verses expressing his warm feelings towards them. Youngest sister, Mary Elizabeth, believed in Riley even when the critics and the public did not. Being short of money Riley created a book of drawings with verse for Mary's birthday. Lesley Payne, Mary's daughter, wrote, "My mother idolized him, and he leaned heavily on her unwavering, militant faith in his ultimate success." Ms. Payne's reminiscences of her uncle are recorded in her unpublished manuscript Random Recollections of a Niece.