James Whitcomb Riley (October 7, 1849 – July 22, 1916) was an American writer and poet also known by the pseudonyms Jay Whit, Benjamin F. Johnson, and Uncle Sidney. During his lifetime he was titled the Hoosier Poet, National Poet, and Children's Poet. He began his career in 1875 writing verses in nineteenth century Hoosier dialect for the Indianapolis Journal. His poems tended to be humorous or sentimental, and of the approximately one thousand poems that Riley published, over half are in dialect. Riley's style was significantly influenced by Robert Burns, to whom he was compared by many critics.

Initially finding it difficult to earn an income as a poet, Riley gradually rose in national prominence during the 1880s through his reading tours. He traveled a circuit with humorist Edgar Wilson Nye and author Douglass Sherley, holding shows and sharing the stage with other well known talents including Samuel Clemens. Regularly struggling with his alcohol addiction, Riley never married or had children, and was involved in a scandal in 1888 when he became too drunk to perform. He became more popular in spite of the bad press he received, and as a result extricated himself from poorly negotiated contracts that limited his earning; he quickly became very wealthy. Riley became a bestselling author beginning in the 1890s and earned a steady income from royalties. His children's books were illustrated by the popular illustrator Howard Chandler Christy. He continued to hold occasional reading shows until 1910 when a stroke paralyzed his right arm; afterward he read only at civic events until his 1916 death. His death made national news and his bier was attended by thirty-five thousand; he is buried at the highest point in Indianapolis at the top of Crown Hill Cemetery. Riley's chief legacy was his influence in fostering the creation of a midwestern cultural identity. Along with other writers of his era, he helped create a caricature of midwesterners and formed a literary community that rivaled the established eastern literati in popular works. During his lifetime he met and befriended many bestselling Indiana authors including Booth Tarkington, George Ade and Meredith Nicholson. Riley achieved a level of fame during his own lifetime that has remained unmatched by other American poets during their own lifetimes. He was honored with annual Riley Day celebrations in many parts of the United States and was regularly called on to speak at national civic events. There are many memorials dedicated to Riley, including the James Whitcomb Riley Hospital for Children.

James Whitcomb Riley was born on October 7, 1849, near the town of Greenfield, Indiana, the third of the six children of Reuben Andrew and Elizabeth Marine Riley. Riley's father was an attorney, and in the year before Riley's birth, he was elected a member of the Indiana House of Representatives as a Democrat. He developed a friendship with James Whitcomb, the governor of Indiana, after whom he named his son. Martin Riley, Riley's uncle, was an amateur poet who occasionally wrote verses for local newspapers. Riley was fond of his uncle who helped influence his early interest in poetry. Shortly after Riley's birth, the family moved into a larger house in town. Riley was "a quiet boy, not talkative, who would often go about with one eye shut as he observed and speculated." His mother taught him to read and write at home before sending him to the local community school in 1852. He found school difficult and was frequently in trouble. Often punished, he had nothing kind to say of his teachers in his writings. His poem "The Educator," which told of an intelligent but sinister teacher, may have been based on one of his instructors. Riley was most fond of his last teacher, Lee O. Harris. Harris noticed Riley's interest in poetry and reading and encouraged him to pursue it further. Riley's school attendance was sporadic, and he graduated from grade eight at age twenty-one in 1869. In an 1892 newspaper article, Riley confessed that he knew little of mathematics, geography, or science, and his understanding of proper grammar was poor. 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.

Riley remained living in his parents' home until he was twenty-one. His childhood introduced him to many people that later influenced his poetry. His father regularly brought home a variety of clients and disadvantaged people to give them assistance. Riley's poem "The Raggedy Man" was based on a German tramp his father hired to work at the family home. Riley picked up the cadence and character of the dialect of central Indiana from the travelers along the old National Road. Their form of speech heavily influenced the hundreds of poems he wrote in nineteenth century Hoosier dialect. At five years old he began spending time at the Brandywine Creek just outside of Greenfield. His poems "The Barefoot Boy" and "The Old Swimmin' Hole" referred back to his time at the creek.

Riley's mother frequently told him stories of fairies, trolls, and giants, and read him children's poems. She was very superstitious, a belief she passed on to Riley. They both filled their homes with "spirit rappings" on places like tables and bureaus to capture any spirits that may have been wandering about. Her influence is recognized in many of his works, including "Flying Islands of the Night."

As was common at that time, Riley and his friends had few toys and they amused themselves with activities. Riley began creating plays and theatricals which he and his friends would practice and perform in the back of a local grocery store. His mother helped him write short songs for the plays. As he grew older, the boys named their troupe the Adelphians and began to have their shows in barns where they could fit larger audiences. Riley wrote of these early performances in his poem "When We First Played 'Show'," where he referred to himself as "Jamesy."

Many of Riley's poems are filled with musical references. Riley had no musical education, and could not read sheet music, but learned from his father how to play guitar, and from a friend how to play the violin. He performed in two different local bands growing up, and became so proficient on the violin he was invited to play with a group of adult Masons at several events.

When Riley was ten, the first library opened in his hometown. From an early age he developed a love of literature. He and his friends spent time at the library where the librarian read stories and poems to them. Charles Dickens became one of Riley's favorites, and helped inspire the poems "St. Lirriper," "Christmas Season," and "God Bless Us Every One."

Riley's father enlisted in the Union Army during the American Civil War, leaving his wife to manage the family home. While he was away, the family took in a twelve year old orphan named Mary Alice "Allie" Smith. Smith was the inspiration for Riley's poem Little Orphant Annie. Riley intended to name the poem Little Orphant Allie, but a typesetter's error changed the name of the poem during printing. Riley's father returned from the war partially paralyzed. He was unable to continue working in his legal practice and the family soon fell into financial distress. The war also had a negative physiological effect on him, and his relationship with his family quickly deteriorated. He opposed Riley's interest in poetry and encouraged him to find a different career path. The family finances finally gave out and they were forced to sell their town home in April 1870 and return to their country farm. Riley's mother was able to keep peace in the family, but after her death in August from heart disease, Riley and his father had a final break. He blamed his mother's death on his father's failure to care for her in her final weeks. He continued to regret the loss of his childhood home and frequently wrote of how it was so cruelly snatched from him by the war, subsequent poverty, and his mother's death. After the events of 1870, he developed an addiction to alcohol with which he struggled for the remainder of his life.

After becoming increasingly belligerent towards his father, Riley moved out of the family home and briefly took a job painting houses before leaving Greenfield in November 1870. He was recruited as a Bible salesman and began working in the nearby town of Rushville. The job provided little income and he returned to Greenfield in March 1871, where he an apprenticeship under a local painter. He completed the study and opened a business in Greenfield creating and maintaining signs. Some of his earliest known poems are verses he wrote as clever advertisements for his customers.

Riley began taking part in local theater productions with the Adelphians to earn a side income, and during the winter months, when the demand for painting declined, Riley began writing poetry which he mailed to his brother living in Indianapolis. His brother began acting as his agent and offered the poems to the Indianapolis Mirror for free. His first poem was featured on March 30, 1872 under the pseudonym "Jay Whit." Riley wrote over twenty poems to the paper, including one that was featured on the front page.

In July 1872, after being convinced sales would provide more income than sign painting, he joined the McCrillus Company based in Anderson. The company sold patent medicines that they marketed in small traveling shows around Indiana. Riley joined the act as a huckster, calling himself the "Painter Poet". He traveled with the act composing poetry and performing at the shows. After his act he would sell his tonics to his audience, sometimes employing dishonesty. During one stop, Riley presented himself as a formerly blind painter who had been cured by a tonic, using himself as evidence to encourage the audience to purchase his product.

Riley began sending poems to his brother again in February 1873. About the same time he and several friends began an advertisement company. The men traveled around Indiana creating large signs, putting advertisements on the sides of buildings and barns, and in high places that would be viewable from a distance. They were pioneers of the concept of billboards in the state, and their trend caught on quickly. The company was financially successful, but Riley was continually drawn to poetry and in October he traveled to South Bend where he took a job at Stockford & Blowney painting verses on signs for a month; the short duration of his job may have been due to his heavy drinking and frequent drunkenness at that time.

In early 1874, Riley returned to Greenfield and began spending more time writing. In February he submitted a poem entitled "At Last" to the Danbury News, a Connecticut Newspaper. The editors accepted his poem, paid him for it, and wrote him a letter encouraging him to submit more. Riley found the note and his first payment inspiring and began focusing even more on his writing. He began submitting more poems to the paper, but after the paper shut down in 1875, Riley was left without a paying publisher. He began traveling with the Adelphians around central Indiana performing to earn an income while he searched for a new publisher. In August 1875 he joined another traveling tonic show ran by the Wizard Oil Company.

Riley began sending correspondence to the famous American poet Henry Wadsworth Longfellow during late 1875 seeking his endorsement to help him start a career as a poet. He submitted many poems to Longfellow, who he considered the greatest poet of the time. Not receiving a prompt response, he sent similar letters to John Townsend Trowbridge, and several other prominent writers looking for an endorsement. Longfellow finally replied in a brief letter, telling Riley that "I have read [the poems] in great pleasure, and think they show a true poetic faculty and insight." Riley carried the letter with him everywhere, and began sending poems to dozens of papers offering to sell them and hoping to receive a job offer. Among the papers to take an interest in the poems was the Indianapolis Journal, a major Republican metropolitan newspaper in Indiana. Among the first poems the paper purchased from Riley were "Song of the New Year," "An Empty Nest," and a short story entitled "A Remarkable Man."

The editors of the Anderson Democrat became interested in Riley's poems that they found in the Indianapolis Journal and offered him a job as a reporter in February 1877. Riley accepted, and although he regularly wrote poems for the paper and continued to sell his poems to larger papers, he worked as a normal reporter gathering local news, writing articles, and assisting in setting the typecast on the printing press. During the year Riley spent working in Anderson, he met and began to court Edora Mysers. The couple became engaged, but decided against marriage in August.

The Kokomo Dispatch , a competitor of the Anderson Democrat, hired a poet to compete with Riley and his paper, and he and Riley began an escalating rivalry. Riley authored a poem imitating the style of Edgar Allan Poe and submitted it to the Dispatch under a fictitious name claiming it was a long lost Poe poem. The Dispatch ran the poem and reported it as such. Riley and two other men who were part of the plot waited several weeks for the poem to become a major news story and was picked up by national papers. Then they wrote scathing reviews calling the poem a hoax, and submitted secret evidence to another rival paper proving the poem was a fake. The revelation caused the public to shun the Dispatch. The Kokomo Tribune, however, learned the truth of the incident and published an expose pointing to Riley as the originator of the hoax.

Riley had difficulty getting his work published after being exposed, but the stigma eventually subsided. In the aftermath he left the Democrat and returned to Greenfield to spend more time writing poetry. Back home, he met Clara Louise Bottsford, a school teacher boarding in his father's home. They found they had much in common, particularly their love of literature. The couple began a relationship that lasted off and on for several years. The relationship soured because of Riley's alcohol addiction in mid 1878. After their break up he made his first attempt to give up liquor and joined a local temperance organization, but quit after a few weeks.

Without a steady income, his financial situation began to deteriorate. He began submitting his poems to more prominent literary magazines, including Scribner’s Monthly, but was informed that although he showed promise, his work was still short of the standards required for use in their publications. Even his contacts at the Indianapolis Journal refused to accept his poetry because of the Poe plot leaving Riley desperate for income. In January 1878, Riley paid an entrance fee to join a traveling lecture circuit. In exchange, he received a portion of the profit his performances earned. Such circuits were popular at the time, and Riley quickly earned a local reputation for his entertaining readings.

In August 1878, Riley followed Indiana Governor James D. Williams as speaker at a civic event in a small town near Indianapolis. He recited a recently composed poem, "A Childhood Home of Long Ago," telling of life in pioneer Indiana. The poem was well received and was given glowing reviews in several newspapers.

"Flying Islands of the Night" is the only play that Riley wrote and published. With similarities to A Midsummer Night's Dream, Riley may have used it as a model. The play concerns a kingdom under siege by evil forces led by a sinister queen who is eventually defeated by an angel-like heroine. Some reviews of the play were mixed, but most were positive. It became popular in the central Indiana area during late 1878, helping Riley to convince newspapers to again accept his poetry. In November 1879 he was offered a position as a columnist at the Indianapolis Journal and accepted after being encouraged by E.B. Matindale, the paper's chief editor.

Although the play and his newspaper work helped expose him to a wider audience, the chief source of his popularity arose from his performances on the lecture circuit. He made both dramatic and comedic readings of his poetry, and by early 1879 could guarantee large crowds whenever he performed. Although he was a good performer, his acts were not entirely original in style; he frequently copied practices developed by Samuel Clemens and Will Carleton and played to his caricature. His tour in 1880 took him to every city in Indiana where he was introduced by local dignitaries and other popular figures, including Maurice Thompson with whom he began to develop a close friendship.

Developing and maintaining his public image became a constant job, and received more of his focus as his fame grew. Keeping his alcohol addiction secret, maintaining the persona of a simple rural poet, and creating the image of a friendly common person became most important. Riley identified these traits as the key to his popularity during the mid 1880s, and wrote of his need to maintain a fictional persona. He fed the persona by focusing on authoring poetry he thought would help build his identity. He was also aided by editorials he authored and submitted to the Indianapolis Journal. He changed his appearance to look more mainstream, and began by shaving his mustache off and abandoning the flamboyant dress he employed in his early circuit tours.

By 1880 his poems were beginning to be published nationally. "Tom Johnson's Quit" was carried by papers in twenty states, thanks in part to the careful cultivation of his popularity. Riley became frustrated that despite his acclaim, he found it difficult to achieve financial success. In the early 1880s, on top of his steady performing, Riley began producing a large number of poems to increase his income. The constant labor had adverse effects on his health, which was worsened by his drinking. At the urging of Maurice Thompson, he again attempted to stop drinking liquor, but was only able to give it up for a few months.

Riley moved to Indianapolis at the end of 1879 to begin his employment with the Journal. It was the only metropolitan paper in Indianapolis with daily editions, and had wide readership. At the paper he wrote a regular society column that often included verses of poetry. Riley disliked living in the city and missed his country home. At the paper, Riley came into contact with many prominent figures, including Eugene V. Debs. Debs wrote Riley several notes commenting on his poetry and complimenting his sentiments. Riley continued to write under the pseudonym Jay Whit until April 1881 when he began using his real name.

Riley renewed his relationship with Bottsford in 1880, and the two corresponded frequently. Their relationship was unstable, but Riley became deeply attached to her. She inspired his poem "The Werewife," which told of a perfect wife who could suddenly turn into a demonic monster. Bottsford pressed Riley for marriage several times, but Riley never gave in. They broke off their relationship a second time in 1881 when she discovered his correspondence with two other women, and found that he had taken a secret vacation to Wisconsin with one of them.

Riley's alcohol addiction also influenced some of his poems during this time, including "On Quitting California," "John Golliher's Third Womern," [sic] and "The Dismal Fate of Tit." Each made references to the delirium caused by drinking. Although Riley rarely published anything controversial, some of his poems published posthumously from the same period, including "Afterwhiles" elude to drug usage and make vague sexual references. Throughout the same time, Riley was still making submissions to the elite literary periodicals, but continued to be rejected. Riley found the rejections depressing, but continued to make regular submissions. He believed he would never be recognized as a true literary figure until one of the prestigious periodicals published his work.

Riley had been making occasional trips to speak around Indiana, and in August was invited to perform at Asbury University. His performance there so impressed the local Phi Kappa Psi chapter, he was invited to join as an honorary member. Through the fraternity he met Robert Jones Burdette, a writer and minister in the Indianapolis area. Burdette was a member of the Redpath Lyceum Bureau of Boston, a prominent lecture circuit who's regular speakers included Ralph Waldo Emerson. Burdette encouraged Riley to join the circuit through its Chicago branch in April 1881. Riley's accumulated debt and low income began causing him trouble in 1881 and he decided rejoining a lecture circuit would provide much needed funds. His agreement for continued employment with the circuit depended on his ability to draw audiences during the first season. The largest audiences Riley drew were in Chicago and Indianapolis, but he had sizable turnout in the rest of the midwest.

Because of his success in the midwest, the circuit leaders invited him to make an east coast tour, starting in Boston at the Tremont Temple in February 1882. Riley agreed, signing a ten year agreement and granting half his receipts to his agent. Before his performance, he traveled to Longfellow's Massachusetts home and convinced him to agree to a meeting. Their brief meeting was one of Riley's fondest memories, and he wrote a lengthy article on it after Longfellow's death only a month later. Longfellow encouraged Riley to focus on poetry, and gave him advice for his upcoming performance. At the performance, Riley was well received and his poems were greeted with laughter and were given praise in the city's newspaper reviews. Boston was the literary center of the United States at the time, and Riley's impression on the city's literati helped him to begin getting his work accepted in the presitgous periodicals. The Century Magazine was the first such periodical to accept his work, finally running "In Swimming-Time" in its September 1883 issue. Until the 1890s, it remained the only major literary magazine to publish Riley's work. Knowing the high standards of the magazine, Riley reserved his best work each year to submit, including one of his favorites, "The Old Man and Jim" in 1887.

By the end of 1882, Riley's finances began to improve dramatically, thanks largely to the income from his performances. During 1883 he began writing his "Boone County" poems under the pen name "Benjamin F. Johnson of Boone." The poems were almost entirely written in dialect and focused on topics of rural life during the early nineteenth century, often using nostalgia and the simplicity of country life as key elements. Among these poems where The Old Swimmin'-Hole and When the Frost Is on the Punkin'. Merrill, Meigs & Company (later renamed Bobbs-Merrill Company) approached Riley to compile the poems into a book. Riley agreed and printing began in August 1883. Their popularity necessitated a second printing before the end of the year. During this period Riley began to determine that the most popular poems were those on topics of rural life, which became a common theme throughout his future work.

The income from Riley's book allowed him to ease his busy work schedule; he began submitting fewer articles to the Journal and made fewer lecture stops. The number of poems he authored slowed, but the quality of his poetry increased; he wrote his most famous poems during this period. Riley attempted to secure a new job at a periodical and leave the Journal, but all the magazines he submitted to would not hire him unless he was willing to move. Riley was steadfast in his refusal to leave Indiana, and told reporters that his rural home was his inspiration and to leave would ruin his poetry.

Riley renewed his relationship with Bottsworth for a third time in 1883. The two corresponded frequently and had secret lovers' rendezvouses. He stopped seeing other women and their relationship became more dedicated. Bottsworth however became convinced Riley was seeing another woman, and they terminated their relationship for the last time in January 1885. Riley's sister Mary had become close friends with Bottsworth and scolded him for his mistreatment of her. Her reputation was largely tarnished by the affair and she found it difficult to find employment once their relationship ended.

In 1884, Riley made another large tour to most of the major cities in the eastern United States. Following the lectures, he began making plans for a second book of poetry. He completed the book during July and Bowen-Merrill published it in December, The Boss Girl, A Christmas Story and Other Sketches. The book, which contained some humorous poetry but mostly short stories, received mixed reviews. It was popular around Indiana, were the majority of its copies were sold. One reviewer, however, called the poems "weird, nightmarish, and eerie," and compared them to some of Edgar Allan Poe's works.

While Riley was working on his book, he was unexpectedly invited by James B. Pond, the agent for many of the nations top performers, to join a one-hundred nights' engagement in New York City in a show that included Samuel Clemens and Dudley Warner. Pond had become a fan of Riley years earlier reading some of his poetry in the newspaper, but was unaware he performed. Riley, however, was unable to reach an agreement with the Redpath Bureau who had to authorize any other performance under the terms of their contract.

In part due to the limited success of his latest book outside Indiana, Riley was finally persuaded to begin working with other midwestern writers to attempt to form an association to promote their work. Popular Hoosier writer Lew Wallace, author of Ben-Hur, was a driving force in the effort. During 1885, over one-hundred writers joined the group. They held their first meeting in July, naming themselves the Western Association of Writers. At the meeting Maurice Thompson was named president, and Riley vice president. The association never succeeded in its goals of creating a powerful advertising force, but became a social club and a rival literati group to the eastern writing establishment. Riley was disappointed in the shortcomings of the group, but came to depend on its regular meetings as an escape from his normally hectic schedule.

Through the association, Riley became acquainted with most of the notable writers in the midwestern United States, including humorist Edgar Wilson Nye of Chicago. After completing his lecture circuit in 1885, Riley formed a partnership with Nye and his agent to begin a new tour. The Redpath Bureau agreed to allow Riley to tour with Nye, provided he maintained his financial agreements with them. In addition to touring, Riley and Nye collaborated to write a book, Nye and Riley's Railway Guide, a collection of humorous anecdotes and poems intended to parody popular tourist literature of the day. Published in 1888, the book was somewhat successful and went through three reprints.

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. The group became known as the International Copyright League and had significant success in its efforts. When traveling to one of the league's meetings in New York City that year, Riley was struck by Bell's palsy. He recovered after three weeks, but remained secluded to hide the effects of the sickness which he believed was caused by his alcohol addiction. He made another attempt to stop drinking with the help of a minister, but again soon returned to his old habit.

After recovering, Riley remained briefly in New York to participate in a show at Chickering Hall with Edgar Nye, Samuel Clemens, and several others. According to reviews, Riley was the star act, and Clemens "shriveled up into a bitter patch of melancholy in the fierce light of Mr. Riley's humour." Clemens disliked being upstaged by Riley, and thereafter attempted to avoid any future joint performances. Riley's poetry brought both tears and laughter according to The New York Sun. Critic Edmund Clarence Stedman, one of the foremost literary critics of the era, was present and wrote that Riley's dialect poems were the finest he had ever heard, "in which a homely dramatis [sic] persona's heart is laid open by subtle indirect, absolutely sure and tender" poetry. As a result of his New York performance, his name and picture were carried in all the major eastern papers and he quickly became well known throughout the United States. Sales of The Boss Girl picked up, leading to the fifth and largest printing.

After returning home Riley finished compiling his third book, which he titled Old-Fashioned Roses, the book was arranged to appeal to British readers. It included only a few of his dialect poems and consisted mostly of sonnets. The book reprinted many poems Riley had already published in newspaper articles, but included some new ones he wrote specifically for the book including "The Days Gone By," "The Little White Hearse," and "The Serenade." The book was Riley's favorite because it contained his finest works and was published by the prestigious Longmans, Green publishers in a high quality binding and print. In late 1888 he also finished work on a fourth book, Pipes o' Pan at Zekesbury which was released to great acclaim in the United States. Based on a fictional town in Indiana, Riley presented many sketches and poems about it citizens and way of life. It received mixed reviews among literary critics who wrote of it that Riley's stories were not of the same quality as his poetry. The book was immensely popular with the public and went through numerous reprints.

Riley was quickly becoming wealthy from his books and touring, earning nearly $20,000 in 1888. He no longer needed his job at the journal, and he left the job near the end of that year. The paper had served as the vehicle taking him to prominence and had published hundreds of his articles. Little Orphant Annie [sic] was the most popular of the poems he wrote for the paper, which during the 1920s served as the inspiration for Little Orphan Annie and Raggedy Ann.

In March 1888, Riley traveled to Washington, D.C. where he had dinner with other members of the International Copyright League at the White House with President of the United States Grover Cleveland. Riley made a brief performance for the dignitaries at the event before speaking about the need for international copyright protections. Cleveland was enamored by Riley's performance and invited him back for a private meeting where the two men discussed cultural topics. In the 1888 Presidential Election campaign, Riley's acquaintance Benjamin Harrison was nominated as the Republican Candidate. Although Riley had shunned politics for most of his life, he gave Harrison a personal endorsement and participated in fund-raising events and vote stumping. The election was exceptionally partisan in Indiana, and Riley found the atmosphere of the campaign stressful, vowing to never become involved in politics again. Upon Harrison's election, he suggested Riley be named the national poet laureate, but Congress failed to act on the request. Riley was still honored by Harrison and visited him at the White House on several occasions to perform at civic events. Riley's participation further boosted his national prominence.

Riley and Nye made arrangements with James Pond to make two national tours during 1888 and 1898. The tours were immensely popular and generally sold out, with hundreds having to be turned away. The shows were usually forty-five minutes to an hour long and featured Riley reading often humorous poetry interspersed by sketches and jokes from Nye. The shows were very flexible and the two men adjusted their performances based on their audiences reactions. Riley memorized forty of his poems for the shows to add to his own flexibility. Many prominent literary and theatrical figures attended the shows. At a New York City show in March 1888, Augustin Daly was so enthralled by the show he insisted on hosting the two men at a banquet with several leading Broadway Theatre actors.

Despite Riley serving as the act's main draw, he was not permitted to become an equal partner in the venture. Nye and Pond both received a percentage of the net profit, while Riley was paid a flat rate for each performance. In addition, because of Riley's past agreements with the Redpath Lyceum Bureau, he was required to pay half of his fee to his agent Amos Walker. This led the other men to profit more than Riley from his own work. 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 and extricate him from some of his previous contracts. Despite discussions and assurances from Pond that he work to address the problem, Eitel had no success. Pond ultimately made the situation worse by booking months of solid performances, not even allowing Riley and Nye a day of rest. These events took a physical and emotional toll on Riley who sank into depression and began his worst period of drinking. During November 1889 Riley became so inebriated at a stop in Madison, Wisconsin, they were forced to cancel several shows.

Walker began monitoring Riley and actively denying him access to liquor so he would be able to perform on the tour, but Riley found ways to evade Walker. 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. He became so drunken, he was not only unable to perform, but unable to travel to the next stop. Nye terminated the partnership and tour in response. The reason for the breakup could not be kept secret, and hotel staff reported to the Louisville Courier-Journal that they saw Riley in a drunken stupor walking around the hotel. The story made national news and Riley feared his career was ruined.

He secretly left Louisville at night and returned to Indianapolis by train. Eitel vociferously defended Riley to the press, explaining the abusive financial arrangements his partners had put him in, which earned him some sympathy. Riley however refused to speak to reporters and hid himself away for weeks. Much to Riley's surprise, the news reports made him more popular than ever. Many people thought the news stories were exaggerated, and Riley's carefully cultivated image made it difficult for the public to believe he was an alcoholic. Riley had stopped sending poetry to newspapers and magazines in the aftermath, but they soon began corresponding with him requesting that he resume writing. This encouraged Riley, and he made another attempt to give up liquor as he returned to his public career.

The negative press did not end however, as Nye and Pond threatened to sue Riley for causing their tour to end prematurely. They claimed to have lost $20,000. Walker threatened a separate suit demanding $1,000. Riley hired Indianapolis lawyer William P. Fishback to represent him and the men settled out of court. The full details of the settlement were never disclosed, but whatever the case, Riley finally extricated himself from his old contracts and became a free agent. The exorbitant amount Riley was being sued for only reinforced public opinion that Riley had been mistreated by his partners, and helped him maintain his image. Nye and Riley remained good friends, and Riley later wrote that Pond and Walker were the source of the problems.

Riley's poetry had become popular in Britain, in large part due to his book Old-Fashioned Roses. In May 1891 he traveled to England to make a tour and what he considered a literary pilgrimage. He landed in Liverpool and traveled first to Dumfries, Scotland, the home and burial place of Robert Burns. Riley had long been compared to Burns by critics because they both used dialect in their poetry and drew inspiration from their rural homes. He then traveled to Edinburgh, York, and London, reciting poetry for gatherings at each stop. Augustin Daly arranged for him to give a poetry reading to prominent British actors in London. Riley was warmly welcomed by its literary and theatrical community and he toured places that Shakespeare had frequented.

Riley quickly tired of traveling abroad and began longing for home, writing to his nephew that he regretted having left the United States. He cut his trip short and returned to New York City in August. He spent the next months in his Greenfield home attempting to write an epic poem, but after several attempts gave up, believing he didn't possess the ability.

By 1890, Riley had authored almost all of his famous poems. The few poems he did write during the 1890s were generally less well received by the public. To remedy the problem, Riley and his publishers began reusing poetry from other books and printing some of his earliest works. When Neighborly Poems was published in 1891, a critic working for the Chicago Tribune pointed out the use of Riley's earliest works, commenting that Riley was using his popularity to push his crude earlier works onto the public only to make money. Riley's newest poems published in the 1894 book Armazindy received very negative reviews that referred to poems like "The Little Dog-Woggy" and "Jargon-Jingle" as "drivel" and to Riley as a "worn out genius." Most of his growing number of critics suggested that he ignored the quality of the poems for the sake of making money.

Although Riley was wealthy from his books, he was able to triple his annual income by touring. He found the lure hard to resist and decided to return to the lecture circuit in 1892. He hired William C. Glass to assist Henry Eitel in managing his affairs. While Eitel handled the finances, Glass worked to organize his lecture tours. Glass worked closely with Riley's publishers to have his tours coincide with the release of new books, and ensured his tours were geographically varied enough to maintain his popularity in all regions of the nation. He was careful not to book busy schedules; Riley only performed four times a week and the tours were short, lasting only three months.

During his 1893 tour, Riley lectured mostly in the western United States, and in his 1894 in the east. His performances were major events, and generally sold out within days of their announcements. In 1894 he allowed author Douglas Sherly to join his tour. Shirley was a millionaire who published his own books. The literary community had dismissed his work, but Riley was instrumental in helping him to be accepted. In 1895 Riley made his last tour, making stops in most of the major cities in the United States. Advertised as his final performances, there was incredible demand for tickets and Riley performed before his largest audiences during the tour. He and Sherly continued a show very similar to those that he and Nye had done. Riley often lamented the lack of change in the program, but found when he tried to introduce new material, or left out some of his most popular poems, the crowds would demand encores until he agreed to recite their favorites.

Following the death of his father in 1894, Riley began regretting his choice to never marry or have children. To compensate for the lack of his own children, he became a doting uncle, showering gifts on his nieces and nephews. He had repurchased his childhood home in 1893 and allowed his divorced sister, Mary, his widowed sister-in-law, Julia, and their daughters to live in the home. He provided for all their needs and spent the summer months living with them. He took his nephew Edmund Eital as a personal secretary and gave him a $50,000 wedding gift in 1912. Riley was well loved by his family.

In the same time, he began compiling his poems of most interest to children into a new book entitled Rhymes of Childhood. The book was richly illustrated by Howard Chandler Christy. Riley authored a few new poems for the book under the pseudonym "Uncle Sydney." "Little Orphant Annie" and "The Raggedy Man" were the most popular of his children's poems, and like many of his others, contained morals and warnings for children. Both of his favorite children's poems contained messages telling children to care for the less fortunate in society. Critics see this as Riley's subtle response to the turbulent economic times of the Gilded Age and the growing progressive movement. Riley believed that the growing urbanization in the nation robbed children of their innocence and sincerity, and in his poems attempted to introduce and idolize characters who had not lost those qualities. Rhymes of Childhood was a major success selling million of copies and helped him earn the nickname the "Children's Poet." Even Riley's rival Clemens commented that the book was "charming" and made him weep for his "lost youth."

Riley had grown very wealthy by the time he ended touring, and was earning $1,000 a week. Although he retired from touring, he continued to make small appearances. In 1896, Riley performed four shows in Denver. Most of the performances in his later life were at civic celebrations. He was a regular speaker at Decoration Day events and delivered poetry before the unveiling of monuments in Washington, D.C. Newspapers began referring to him as the "National Poet", "the poet laureate of America", and "the people's poet laureate". Riley wrote many of his patriotic poems for such events, including "The Soldier", "The Name of Old Glory", and his most famous such poem, "America!". The 1902 poem "America, Messiah of Nations" was written and read by Riley for the dedication of the Indianapolis Soldiers' and Sailors' Monument.

The only poetry Riley published after the turn of the century were elegies for famous friends. The poetic qualities of the poems were often poor, but they contained many popularly held sentiments concerning the deceased. Among those he eulogized were Benjamin Harrison, Lew Wallace, and Henry Lawton. Because of the poor quality of the poems, some of his friends and publishers requested that he stop writing them, but he refused.

In 1897, Riley's publishers suggested that he create a multi-volume series of books containing his complete life works. With the help of his nephew, Riley began working to compile the books, which eventually totaled sixteen volumes and were finally completed in 1914. Such works were uncommon during the lives of writers, attesting to the unusual level of popularity Riley had achieved. Although Riley had given up touring, he did continue to speak at public events and attend banquets in his honor.

Universities began offering him honorary degrees during the 1910s. His works had become staples for Ivy League literature courses. Yale was the first to offer him such a degree in 1902. The University of Pennsylvania followed in 1904, making him a Doctor of Letters. Wabash College and Indiana University granted him similar awards. In 1908 he was elected member of the National Institute of Arts and Letters, and in 1912 they conferred upon him a special medal for poetry.

Riley was influential in helping other poets start their careers, having particularly strong influences on Hamlin Garland, William Allen White, and Edgar Lee Masters. He also discovered aspiring African American poet Paul Laurence Dunbar in 1892. Riley thought Dunbar's work was "worthy of applause", and wrote him letters of recommendation to help him get his work published.

In 1901, Riley's doctor diagnosed him with neurasthenia, a nervous disorder. They recommended long periods of rest as a cure. Riley remained ill for the rest of his life. He began boarding in a home in Indianapolis' Lockerbie district, then a small suburb. There his hosts met all his needs and became his close friends. During the winter months he moved to Miami, Florida, and during summer spent time with his family in Greenfield. He made only a few trips during the decade, including one to Mexico in 1906. He became very depressed by his condition, writing to his friends that he thought he could die at any moment, and often turned to alcohol for relief.

In March 1909, Riley was stricken a second time with Bell's palsy, and partial deafness, the symptoms only gradually eased over the course of the year. Riley was a difficult patient, and generally refused to take any medicine except the patent medicines he had sold in his earlier years; the medicines often worsened his conditions, but his doctors could not sway his opinion. On July 10, 1910 he suffered a stroke that paralyzed the right side of his body. Hoping for a quick recovery, his family kept the news from the press until September. Riley found the loss of use of his writing hand the worst part of the stroke, depressing him more. With his health so poor, he decided to work on a legacy by which to be remembered in Indianapolis and in 1911 donated land and funds to build a new library on Pennsylvania Avenue. In 1913, with the aid of a cane, Riley began to recover his ability to walk. His inability to write nearly ended his production of poems. George Ade worked with him from 1910 through 1916 to write his last five poems and several short autobiographical sketches as Riley dictated. His publisher continued recycling old works into new books, which remained in high demand.

Since the mid-1880s, Riley had been the nation's most read poet, a trend that accelerated at the turn of the century. Demand for his works was so large that the level of popularity he achieved has not since been surpassed by any poet in their lifetime. In 1912 Riley recorded readings of some of his most popular poetry to be sold by Edison Records. Painter T.C. Steele, a friend of Riley's, created three portraits of Riley. The Indianapolis Arts Association commissioned a portrait of Riley to be created by world famous painter John Singer Sargent. Riley's image became a nationally known icon and many businesses capitalized on his popularity to sell their products.

In 1912, the governor of Indiana instituted Riley Day on the poet's birthday. Schools were required to teach Riley's poems to their children, and banquet events were held in his honor around the state. In 1915 and 1916 the celebration was national after being proclaimed in most states. The annual celebration continued in Indiana until 1968. In early 1916 Riley was filmed as part of a movie to celebrate Indiana's upcoming centennial, the video is on display at the Indiana State Library.

On July 22, 1916, Riley suffered a second stroke. He recovered enough during the day to speak and joke with his companions. He died before dawn the following morning, July 23. Riley's death shocked the nation and made front page headlines in all the major newspapers. Indiana Governor Samuel M. Ralston offered to allow Riley to lay in state at the Indiana Statehouse — Abraham Lincoln being the only other person to have previously received such an honor. During the ten hours he laid in state on July 24, over thirty-five thousand filed past his bronze casket; the line was still miles long at the end of the day and thousands were turned away. The following day a private funeral ceremony attended by many dignitaries was held. A large funeral procession then carried him to Crown Hill Cemetery where he was buried in a tomb at the top of the hill, the highest point in the city of Indianapolis.

Within a year of Riley's death, several memorials were created, including several by the James Whitcomb Riley Memorial Association. The James Whitcomb Riley Hospital for Children was created and named in his honor by a group of wealthy benefactors and opened in 1924. In the following years, other memorials were created, including Camp Riley for Youth with Physical Disabilities. The memorial foundation purchased the poet's Lockerbie home in Indianapolis and it is now maintained as a museum. The James Whitcomb Riley Museum Home is the only late Victorian home in Indiana that is open to the public and the country's only late Victorian preservation, featuring authentic furniture and decor from that era. His birthplace and boyhood home, now the James Whitcomb Riley House, is also preserved as a historical site. James Whitcomb Riley High School opened in South Bend, Indiana in 1924. In 1950, there was a James Whitcomb Riley Elementary School in Hammond, Indiana, but it was torn down in 2006. East Chicago, Indiana, had a Riley School at one time, as did neighboring Gary, Indiana, and Anderson, Indiana.

As a lasting tribute, the citizens of Greenfield hold a festival every year in Riley's honor. Taking place the first or second weekend of October, the "Riley Days" festival traditionally commences with a flower parade in which local elementary school children place marigolds around the statue of Riley on the county courthouse lawn, while the Greenfield - Central High School band plays lively music in honor of the poet. The larger Riley parade is on that Saturday and is a fall attraction. The Greenfield - Central High School band also holds their annual Riley Marching Festival on that same day. Other music and entertainment events are held at the Court House Plaza and the H.J. Ricks Centre for the Arts.

A Liberty ship, commissioned April 23, 1942, was christened the SS James Whitcomb Riley. It served with the United States Maritime Commission until being scrapped in 1971.

According to historian Elizabeth Van Allen, Riley was instrumental in helping form a midwestern cultural identity. Before the 1880s, the midwestern United States had no significant literary community and was largely shaped by the cultural influences of other regions of the United States. The works of the Western Assocation of Writers, most notably Riley and Wallace, helped create the midwest's cultural identity and create a rival literary community to the established eastern literari. For this reason, and the publicity Riley's work created, he was most commonly known as the "Hoosier Poet."