James Whitcomb Riley’s writing opportunities increased with his move to Indianapolis. He worked for the Indianapolis Journal and continued writing on his own. His first real success came with a series entitled “Benjamin F. Johnson of Boone”. Riley wrote in the American
vernacular and is known as "The Hoosier Poet." His first book was "The Old Swimmin’ Hole and ‘Leven More Poems." Some of his more popular works are "Little Orphan Annie" and "The Raggedy Man." Riley was also an eloquent speaker. Upon his rise in popularity, much time was spent on the lecture circuit.
Riley lived at a brick home in Lockerbie Square, Indianapolis’ oldest historic district, from 1893-1916. He did not actually own the 1872 house. He rented a suite of rooms from Charles Holstein for twenty-three years. Much of his later writing was done at this house, and famous people came to visit him here. In 1915, Riley had a
stroke, and he died the following year in this house.