This dissertation presents an in-depth examination of Sumiyoshi Gukei’s (住吉 具慶, 1631–1705) masterwork handscrolls Illustrated Legends of the Two Masters (Ryōdaishi engi emaki, 1680), pictorial biographies of the Tendai Buddhist patriarchs Tenkai (天海, 1536–1643) and Ryōgen (良源, 912–985). These scrolls played a crucial role in Gukei’s 1685 appointment to shogunal painter (goyō eshi), distinguishing him as the first artist trained in the native yamato-e style to be hired to the position by the Tokugawa. Illustrated Legends of the Two Masters demonstrates the manner in which Gukei utilized visual tropes steeped in the prestige of an idealized past to devise an entirely new iconography suitable to satisfy the desires of Kan’eiji, the shogunal temple that commissioned these narratives. The yamato-e of the Edo period inherently embodies a tension between lionizing the visual tropes of the historic past and refreshing them with novel interpretations, a balance perfectly struck by Gukei’s expressive, idiosyncratic, and narratively rich take on the mode. From its founding in 1663, the members of Sumiyoshi school had a reputation for working in an orthodox style of yamato-e, resulting from the Tosa school training of the founder Sumiyoshi Jokei (住吉 如慶, 1598–1670), and his thorough experience copying classic paragons of courtly grace; as the second head of the school, Gukei’s interpretation exhibits a noteworthy departure from previous conventions. This deft appropriation of imperial visual culture and adroit repackaging to suit contemporary tastes appealed to the Tokugawa shogunate, itself seeking a visual vocabulary with which to maintain cultural dominion over the realm.