Whether wielding a pencil, pen, or paint brush, Riley's skill as an artist is evident. Throughout his life Riley used art as an alternative means to display his acute observations of people. An indifferent student at best, except when it came to literature, Riley last attended school in 1870. After a brief and decidedly unsuccessful stint selling Bibles to the populace of Rushville, Indiana, Riley became apprenticed to John Keefer, a sign painter. His natural artistic ability quickly manifested itself and rhyming was a feature of his work. Within a year Keefer declared that he had taught Riley all he knew and encouraged the young man to go out on his own. Keefer provided Riley with the necessary tool kit to set up business and the poet began versifying in paint.
In 1872 Dr. Samuel B. McCrillus rolled into Greenfield with his "Popular Standard Remedies" medicine show. Working for McCrillus was a sign painter named James McClanahan. When McCrillus and McClanahan left Greenfield Riley went with them as a second sign painter and front man. The trio traveled throughout Indiana and parts of Ohio. Their program consisted of McCrillus hawking the bottles of remedies and musical interludes featuring McClanahan and Riley playing the banjo and guitar. It wasn't long before Riley was composing lyrics for show, as well as reciting verses and telling comic stories.
McClanahan and Riley left the medicine show in the spring of 1873
and formed "The Riley & McClanahan Advertising Company" which painted
advertising slogans on Hoosier barns. The company quickly expanded
to four painters and the name was changed to "The Graphics." The
fellows plied their trade across the state, experiencing the highs
and lows of life as itinerant painters. Still, Riley hungered for
the opportunity to write verses. He left The Graphics, went back
to Greenfield, and began to write. In 1875 Dr. C. M. Townsend and
The Wizard Oil Company came to town. Townsend's show was much
larger than the McCrillus operation, employing ten professional
musicians and comic players. Townsend sold his medicines against a
backdrop of vaudeville and musical performances. Riley could not
resist the lure of joining such a company and when the Wizard Oil
Company left Greenfield, Riley was a member of the troupe.