Uncomplicated, sentimental, and humorous. Often writing his verses in dialect, his poetry caused readers to recall a nostalgic and simpler time in earlier American history. His poems often contained morals and warnings for children, containing messages telling children to care for the less fortunate of society.

Riley believed that urbanization robbed children of their innocence and sincerity, and in his poems he attempted to introduce and idolize characters who had not lost those qualities. His children's poems are "exuberant, performative, and often display Riley's penchant for using humorous characterization, repetition, and dialect to make his poetry accessible to a wide-ranging audience."

Riley wrote very little on serious subject matter, and actually mocked attempts at serious poetry. Riley wrote gentle and romantic poems that were not in dialect.

One of the most popular poets in American history, James Whitcomb Riley was born in Greenfield, Indiana, the second son and third of six children raised by Reuben A.(a Civil War veteran and lawyer)and Elizabeth (Marine) Riley. At an early age Riley discovered that he disliked the "iron discipline" of school life but enjoyed books. As a child, Riley often accompanied his father (a noted political orator) on trips to the Hancock County courthouse, where he observed the manners and mores of country society, as well as the countrified dialect he later used in his poetry. 

In his own words he did a little of a number of things fairly well.      He sang, played the guitar and violin, acted, painted signs and wrote poetry. His father did not encourage his verse-making for he thought it too visionary, and being a visionary himself, he believed he understood the dangers of following the promptings of the poetic temperament. He doubted if anything would come of the verse-writing himself. 

Leaving school at age 16, Riley first attempted to read law in his father`s office. Possessed of a wanderlust, however, he turned to another pursuit,art. He and some other youths, which he dubbed "the Graphics," traveled the Indiana countryside as sign, house and ornamental painters. He later joined a traveling wagon show as an advance agent. In 1873, Riley returned to Greenfield and worked for the town`s newspaper. A year earlier, his poetry, under the name "Jay Whit," had first appeared in the Indianapolis Saturday Mirror. 

In April 1877, Riley joined the staff of the Anderson Democrat as associate editor. He continued to write poems, which were printed in other newspapers throughout central Indiana. Frustrated, however, at his poems being rejected by eastern periodicals, Riley concocted a scheme to prove that for a poem to become popular it had to be written by "a genius known to fame." He wrote a poem, "Leonainie," styled after Edgar Allan Poe, and convinced the editor of the Kokomo Dispatch to print it in his newspaper as a long-lost Poe poem. Unmasked as the poem`s true author, Riley was lambasted by rival newspapers and eventually fired from his Anderson job. 

Despite the notoriety he earned from the Poe poem hoax, Riley managed to find employment with another newspaper, the Indianapolis Journal. It was while on the Journal staff that he first won acclaim for his work, especially "When the Frost Is on the Punkin," part of a series he signed "Benj. F. Johnson, of Boone." The series was published in book form in 1883 and met with popular success. 

Riley`s characters Old Aunt Mary, Little Orphant Annie, The Raggedy Man, Doc Sifers and Uncle Sidney along with his sentimental style that harkened back to simpler times, struck a chord with a reading public struggling to come to grips with the industrial age. Riley increased his fame as a poet and helped himself financially through his appearances on the lecture circuit with, among others, Edgar W. (Bill) Nye. 

Riley, whose books were regularly published by Indianapolis`s Bobbs-Merrill Company, became one of the best-loved poets in America. A lifelong bachelor, Riley spent most of his days of fame as the paying guest in a Lockerbie Street home owned by the Nickum and Holstein families, residing there from 1893 until his death in 1916. The home became a regular visiting place for Indiana schoolchildren and famous figures like perennial Socialist presidential candidate and labor organizer Eugene Debs (who enjoyed raising a glass of spirits with Riley whenever possible). Riley`s fame grew so great that his birthday was celebrated by students across the country. Upon his death on July 22, 1916, more than 35,000 people filed past his casket as it lay in state under the dome at the Indiana State Capitol.

(source indianahistory.org)