This study examines the works of Roger Shimomura. I argue that the ukiyo-e elements infuse the artist's paintings and prints with a secondary iconography that is overlooked by art historians to date. I accept Shimomura's assertions that he is completely unfamiliar with the iconography of Japanese art. However, I assert that his use of this visual sign system creates new meanings in the eyes of educated viewers, beyond the intentions of the artist. In addition, I argue that Shimomura adopts visual rhetorical devices that aid in the didactic function of many of his works. This study explores how Shimomura creates and communicates ideas within individual works. Moreover, I examine particular figures that appear repeatedly in his art over time, and how these figures develop meanings that are particular to Shimomura's works. Underlying the entirety of this study is Shimomura's exploration of identity, both ethnic and personal. I utilize literature from numerous fields, including art history, history, Asian studies, literature, anthropology, and sociology. These enrich the contextual sources, including reviews of Shimomura's works, articles from journals and newspapers, and other works of art. All of this supplements interviews with Shimomura, as well as primary documents, such as his artist's statements, essays, and personal papers. Together, these materials help to create an understanding of not only the artist's working methods and intentions, but also his inspirations. In addition, the critical approaches allow me to discuss how his works are entrenched in socio-political contexts that may not be immediately apparent. Finally, these sources open up new discourses on Shimomura's ouvre, including how he adopts disparate visual languages and utilizes them to didactic ends.