Hashimoto Kunihiko (1904–1949) was one of the most versatile but also most contradictory composers in pre-Pacific War Japan. Although originally known as a radical and anti-academic modernist who embraced new compositional techniques in the late 1920s and early 1930s, Hashimoto came to follow a more conservative approach in the late 1930s. With their stylistic versatility, Hashimoto’s art songs embodied many of the cultural contradictions apparent in Japanese music and society at that time. Most notably, they communicate a contrast between modern and traditional Japan. This chapter focuses on the ways that Hashimoto’s interest in premodern Japanese music manifested and developed in his work and thought during the 1920s and 1930s. The analyses show that he utilized elements from premodern genres in a variety of ways, ranging from modernist composition to an expression of nostalgia for a (possibly imaginary) rural Japan. These aspects were closely linked with the contemporary intellectual and artistic context, making Hashimoto’s art songs a musical representation of the changes Japan was undergoing at that time.