This dissertation investigates the work of Ogata Korin (1658--1716), one of the most idiosyncratic artists of Japan's early modern period. By employing aspects of literature and theater, as well as a focus on Korin's experimentations with the effects of style, materials, and artistic media, I elucidate how his oeuvre is characterized by a continuous strive to test the faculties of painting. Following a chronological approach, the four chapters of the dissertation trace Korin's life and work from his early steps as a painter to the collaboration with his brother Kenzan (1663--1743) during his final years. The chapters are framed by an introduction, a conclusion, and an appendix. The first chapter focusses on Korin's earliest works: two hanging scrolls depicting the medieval poet Sogi (1421--1502) and Hotei Playing Kemari, as well as a pair of screens entitled Poetic Meanings of the Twelve Months. These works reveal Korin's intellectual indebtedness to late medieval culture and the imperial court. Korin's initial engagement in the arts occurred alongside his first confrontation with medieval ink modes, which laid the foundations for Korin's lifelong understanding of that material. Numerous contemporary sources testify to Korin's passion for the Noh theater. This little-studied, formative period of Korin's life established his aesthetic sensibilities and is thus critical for understanding his art, a connection examined in the second chapter. Korin's perennial engagement with Noh put him in contact with high-level aristocrats, such as the Nijo family, as well as upper-tier clergy at the temples Daigoji and Nishi Honganji. The theater also provides a possible reading of key works by Korin, such as his screen painting Irises. The third and fourth chapters explore Korin's diversified dialogue with the material qualities of ink. The third chapter surveys his appropriation of a particular technique, tarashikomi, first championed by Tawaraya Sotatsu (d. ca. 1640). I propose that Korin turned to tarashikomi as he prepared to leave his native Kyoto for Edo, where he was active for around five years. The chapter argues that Korin used tarashikomi, a painting method associated with Kyoto culture, to solicit clients in the shogunal capital of Edo. The last chapter is devoted to Korin's collaboration with Kenzan. From the 1710s onward, the brothers created numerous examples of sabi-e, works in iron oxide on square ceramic vessels that emulate the techniques and visuality of paintings in ink. This unprecedented expansion of the boundaries of one medium to envelop another resulted in approximations of traditional ink paintings in ceramics. In the process, Korin expanded the paradigm of ink to include an entirely new material component. The appendix includes the first complete English-language translation of the collection of extant Edo-period letters and other documents by and about Korin that are contained in the Konishi Archives, held at the Kyoto National Museum, the Osaka Municipal Museum, and various other collections in Japan.