Both a print artist and poet, scholars suggest that Yoshikuni was the son of Hakuensai Baiko, the proprietor of the Osaka publishing firm Shioya Saburobei. Yoshikuni released an anthology of poetry in 1800, but did not begin his print career until 1813, signing his works “Juko.” He soon joined the Shikuni school and assumed the name "Ashimaro." In 1816, he made the transition to the name “Yoshikuni,” signing a work “Ashimaro changing to Yoshikuni.” His early career is marked by two collaborative triptychs produced in 1817, designed with Ashiyuki and Ashihisa respectively.

Yoshikuni produced well over one hundred designs between 1820 and his last known work in 1832. While his poetry focus on the history and landscape of Osaka, his prints capture the beloved stars of Osaka: the Kabuki actors. His compositions favor the actor Utaemon III, but are not restricted to the most famous actors. Yoshikuni equally portrays actors from mid-range theaters and visiting talents. Though Yoshikuni was not a formal head of a school, he was the head of the Jukodo circle in Osaka. This group was known for their sensitivity to the rich identities and interconnectedness of the theatrical, literary and artistic circles in Osaka.