With other writers of his era, he helped create a caricature of Midwesterners and formed a literary community that produced works rivaling the established eastern literati.

[12] Later critics, like Henry Beers, pointed to his poor education as the reason for his success in writing; his prose was written in the language of common people which spurred his popularity.

With his mother's help, Riley began creating plays and theatricals, which he and his friends would practice and perform in the back of a local grocery store.

[13][25] Becoming increasingly belligerent toward his father, Riley moved out of the family home and briefly took a job painting houses before leaving Greenfield in November 1870.

[43] Longfellow finally replied in a brief letter, telling Riley, "I have read [the poems] in great pleasure, and think they show a true poetic faculty and insight.

"[44][45] Riley carried the letter with him everywhere and, hoping to receive a job offer and to create a market for his poetry, he began sending poems to dozens of newspapers touting Longfellow's endorsement.

[51][52] Riley and two other men who were part of the plot waited two weeks for the poem to be published by major newspapers in Chicago, Boston, and New York to gauge their reaction; they were disappointed.

Riley began submitting his poems to more prominent literary magazines, including Scribner's Monthly, but was informed that although it showed promise, his work was still short of the standards required for use in their publications.

[68] His tour in 1880 took him to every city in Indiana where he was introduced by local dignitaries and other popular figures, including novelist Maurice Thompson with whom he began to develop a close friendship.

Burdette was a member of the Redpath Lyceum Bureau of Boston, a prominent lecture circuit whose regular speakers included Ralph Waldo Emerson.

[89] Riley's accumulated debt and low income began causing him trouble in 1881, and he decided that rejoining a lecture circuit would provide much needed funds.

[103] The income from his book allowed Riley to ease his busy work schedule; he submitted articles to the Journal less often and made fewer lecture stops.

[111][112] While Riley was working on his book, he was unexpectedly invited by James B. Pond, the agent for many of the nation's major performers, to join a one-hundred nights' engagement in New York City in a show that included Samuel Clemens and Dudley Warner.

[117] The association never succeeded in its goal of creating a powerful advertising force, but became a social club and a rival literary community to the eastern writing establishment.

[118] Through the association, Riley became acquainted with most of the notable writers in the Midwestern United States, including humorist Edgar Wilson Nye of Chicago.

[99] In October 1887, Riley and the association joined with other writers to petition the United States Congress to attempt to negotiate international treaties to protect American copyrights abroad.

At a New York City show in March 1888, Augustin Daly was so enthralled by it he insisted on hosting the two men at a banquet with several leading Broadway theater actors.

[125] To remedy this situation, Riley hired his brother-in-law Henry Eitel, an Indianapolis banker, to manage his finances and act on his behalf to try to extricate him from his contract.

At a stop at the Masonic Temple Theatre in Louisville, Kentucky, in January 1890, Riley paid the hotel's bartender to sneak whiskey to his room.

[170][173] Riley was influential in helping other poets start their careers, having particularly strong influences on Hamlin Garland, William Allen White, and Edgar Lee Masters.

His image became a nationally known icon and many businesses capitalized on his popularity to sell their products; Hoosier Poet brand vegetables became a major trade-name in the Midwest.

It was not until almost a year and half later October 6, 1917, the day before what would have been his birthday, that his casket was buried in a tomb during a private ceremony at the top of the hill, the highest point in the city of Indianapolis.

The pageant has been going on many years in honor of the Hoosier poet[198] According to historian Elizabeth Van Allen, Riley was instrumental in helping form a Midwestern cultural identity.

[199] The works of the Western Association of Writers, most notably those of Riley and Wallace, helped create the Midwest's cultural identity and rival literary community to the established eastern literati.

David Galens and Van Allen both see these messages as Riley's subtle response to the turbulent economic times of the Gilded Age and the growing progressive movement.

[204] 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".

They generally consist of sonnets and are strongly influenced by the works of John Greenleaf Whittier, Henry Wadsworth Longfellow, and Alfred, Lord Tennyson.

Galens wrote modern critics consider Riley to be a "minor poet, whose work—provincial, sentimental, and superficial though it may have been—nevertheless struck a chord with a mass audience in a time of enormous cultural change".

[202] Thomas C. Johnson wrote that what most interests modern critics was Riley's ability to market his work, saying he had a unique understanding of "how to commodify his own image and the nostalgic dreams of an anxious nation".

Philip Greasley wrote that while "some critics have dismissed him as sub-literary, insincere, and an artificial entertainer, his defenders reply that an author so popular with millions of people in different walks of life must contribute something of value, and that his faults, if any, can be ignored".