The problem of the formation of colonial modernity and identity politics in the Japanese colonial Taiwan has recently received many scholarly discussions. This study takes up the issue homeland by exploring three works of Chen Cheng-po concerning his hometown Chiayi in order to investigate the problems about Taiwanese subjectivity and identity under the colonial condition. This paper divides the discussion into two sections. The first section deals with Chen Cheng-po's two early works about Chiayi's landscape and street scenes, ”Outside of a Chiayi Street” (1926) and ”Street Scene on a Summer Day” (1927), when he studied arts and painting in Tokyo. I argue that Chen's works at the time presented the emergence of his homeland consciousness and its relation with the rise of Taiwanese nationalism. The double structures on the paintings that revealed images of the Nangoku (Southland) and modernity, which were both inevitably influenced by the received official idea of the Taiwan as a Southland the Japanese colonizer invested, transform their relation from conflict to fusion. By such an operation, Chen tried to remove elements that might threaten his sense of existence for reconstituting his own identity. The second part analyzes Chen's another work ”Chiayi Park” (1937). He produced this painting when he returned home. He mobilized East Asian traditional painting languages from multiple sources. During this period Chen frequently emphasized the ideal of the Toyo, literally Orientalism. Although the Toyo ideal had its Japanese origins, Chen relocated in the painting the center of Toyo to Taiwan. With this move, Chen painted the ”Chiayi Park” in a style of embracing multiple cultural elements for drawing an ideal image of the homeland. In it, concentrating on the colorful giant flame tree as we should see, Chen made a way of pursuing his subjectivity. The drawings of homeland scenes in Chen's paintings transformed at different stages. However, the repeated theme of the relationship between mother and son may suggest that the resource of identity came from his sense of morality based upon his deep love in family.