riley began his career writing verses as a sign maker and submitting poetry to newspapers. thanks in part to poet henry wadsworth longfellow's endorsement, he eventually earned successive jobs at indiana newspaper publishers during the late 1870s. he gradually rose to prominence during the 1880s through his poetry reading tours. he traveled a touring circuit first in the midwest, and then nationally, appearing either alone or with other famous talents. during this period riley's long-term addiction to alcohol began to affect his performing abilities, and he suffered financially as a result. however, once he extricated himself from a series of poorly negotiated contracts that sought to limit his earnings, he began to accumulate wealth and eventually became a financial success.