My dissertation investigates the foreign and domestic forces instrumental in the development of modernist abstract painting in postwar Taiwan between 1957 and 1968. My work contributes to the discourse of postwar abstract painting and modernism by providing a critical study of the relationship between calligraphy, ink painting, and abstraction. Mainland-born, Taiwan-educated artists continued the unfinished project of May Fourth by conducting the first thorough re-examination of Chinese art traditions and interacting with European and American modern art currents. Against a backdrop of post-colonial cultural reorientation, post-civil war social reconstruction, martial law, and Cold War geopolitical realities, abstraction emerged as a style that upheld traditional Chinese aesthetic principles, that translated personal experiences of displacement, and that promised readability in the international arena. The first two chapters examine the emergence of abstraction from outward- and inward-looking angles, respectively. Chapter One examines the curatorial agenda and interests behind “The New Chinese Landscape: Six Contemporary Chinese Artists,” the first major exhibition of contemporary Chinese art, 1966–1968. Chapter Two considers the pivotal role of two literature and arts magazines, Wenxing and Bihui, as cultural producers and dialogue generators in the formation of Taiwan Modernism. It highlights the tight relationship between the artists and poets as they constructed a discourse for modernism. Chapter Three traces the evolution of the meaning of abstraction in postwar Taiwan, paying special attention to the “abstract landscape” by Liu Kuo-sung and Chuang Che, the most prominent artists of the Fifth Moon Society. Chapters Four and Five look at the respective practices of Liu and Chuang and offer detailed formal analysis of their paintings, especially on their treatment of calligraphy and abstraction. In Chapter Four, I analyze the artistic trajectory of Liu and the development of his vernacular landscape paintings throughout the 1960s. In Chapter Five, I identify Chuang’s use of brokenness as an aesthetic that confronts the predicament of displacement. In both chapters I examine the patronage and reception of their work outside of Taiwan to place them in the larger discourse of postwar abstraction and show the challenges in traversing cultural boundaries for transnational artists of their postwar generation.