The painting Tōhon miei 唐本御影 is allegedly the earliest portrait of Japanese Prince Shōtoku (c.573–622), traditionally regarded as the first royal patron of Buddhism. This article will discuss this particular portrait from three viewpoints: questions concerning the identity of its artist, the painting style, and its socio-historical background. Each of these three facets demonstrates cultural interaction between ancient Korea and Japan. In this light, this article begins from an examination of whose brush actually painted it, followed by an analysis of its style and the Buddhist elements of this painting. These then lead to the third part of the research, which discusses its historical context in ancient East Asia. The conclusion sheds light on the complexity of cultural interactions in East Asian art through this case of the symbolic figure of Prince Shōtoku. The processes of conception, mutual learning, and reinterpretation between the two cultures are crystallised in this artistic product of royal portraiture.