In 1888 Riley teamed up with Edgar Wilson "Bill" Nye, newspaper columnist and humorist, and the two began touring the country for Major James B. Pond's Lyceum Bureau. The comic work of Nye complimented the dialect sketches of Riley and they were enormously popular figures on the lecture circuit. Nye and Riley appeared almost nightly, in city after city, alternating their stage performances to the immense satisfaction of audiences everywhere. It was a strenuous schedule which affected the health of both men. The contract negotiated between Pond and Riley was disadvantageous to the Poet and Riley began to feel used by Pond. The stress of the situation led to an abuse of alcohol which affected Riley's ability to perform. While in Louisville, Kentucky, Riley became so inebriated after a performance that he was unable to travel the next day. The scandal broke in the Louisville newspapers. The story was most likely exaggerated, but Riley's drinking, which in this case was a symptom of an overall breakdown, led to an abrupt end to the tour. Riley admitted that he was culpable. Despite the ensuing scandal, he was able to salvage his career. Henry Eitel, Riley's brother-in-law, immediately deflected attention away from Riley's drinking by divulging the Poet's situation with his contract and by explaining that he, of course, had a very sensitive poetic temperament. Indianapolis society stood by the poet and the Indianapolis Literary Club sponsored a reception in his honor. Notices of this reception were published in newspapers across the country.
When Riley abruptly abandoned the platform in 1890 the public believed
that he and Nye had quarreled. There was much speculation in the newspapers
and magazines, but neither Nye nor Riley would comment. Nye continued to
perform as a soloist and in conjunction with other celebrities.
Representative samples of Riley's and Nye's sketches appeared in 1888 as
Nye and Riley's Railway Guide. This collaborative piece, published in
Chicago by The Dearborn Publishing Company, was intended to provide
entertainment for the traveler. It was enormously popular and the first
edition sold out within a week.