Two of the most famous and best loved of Riley's poems are "The Raggedy Man" and "Little Orphant Annie." "The Raggedy Man" first appeared in the December 1890 issue of the Century Magazine and was included in Riley's most successful book, Rhymes of Childhood, published in 1891 by The Bowen-Merrill Company. The edition was dedicated to Riley's nephew Edmund Henry Eitel and contained a photograph of Riley with Eitel seated on his knee as the frontispiece. It was reissued in 1891 and again in 1895 as part of the Homestead Edition, which omitted twenty of the original poems, replacing them with seventeen others of which five were first appearances in book form. In 1907 the poem was published by the Bobbs-Merrill Company in book form with four additional stanzas and illustrations by Ethel Franklin Betts.
The poem we familiarly call "Little Orphant Annie" was first printed in the Indianapolis Journal on November 15, 1885 as "The Elf Child." It appeared under that title in Character Sketches The Boss Girl, a Christmas Story and other Sketches published by the Bowen-Merrill Company in 1886. Orphaned during the American Civil War, Annie, whose name was actually Mary Alice Allie Smith, came to stay with the Riley family in Greenfield during the winter of 1862. She performed household chores in exchange for her room and board. Allie enchanted the Riley children with tales, warning of the goblins below the stairs. When next published Riley altered the title to "Little Ophant Allie," but a typesetting error turned Allie into Annie. Riley contacted his publisher about a correction, but upon being informed that the edition was selling extremely well, he decided to leave the error intact. Allie grew up, married a fellow named Grey, and moved to the Indiana town of Philadelphia. When she was 74 she visited the Greenfield home. It was not until she was in her 70's that she knew that she was the heroine of Riley's poem.
Riley and Joel Chandler Harris were both enthusiasts of the phonograph. They
discussed it in their correspondence and exchanged recordings with one another.
In 1912 the Victor Talking Machine Company produced nine recordings of Riley
reading his poems. Of these only four recordings were issued-"The Raggedy Man,"
"Little Orphant Annie," "The Happy Little Cripple," and "Out to Old Aunt Mary's."