This dissertation explores Korean writers’ pursuit of decolonization during the politically turbulent era from 1945 to 1950. Decolonization of this period was both from the Japanese empire, the colonial past, and from the newly established national division and Cold War order, the ongoing “neocolonial” present. Literary representations of colonial collaboration (ch’inil) were complicated in Korea’s decolonization process under the solidifying political polarization. Investigating diverse transformations, inflections, and repeated resurfacings that arose in representations of collaboration, this dissertation pays particular attention to the struggles, predicaments, and anxieties faced by postcolonial Korean writers as they grappled with the colonial past and current neocolonial contexts. The dissertation mainly presents two comparable genres: autobiographical writings, the facticity of which is often challenged, and long serial novels. Chapter One examines selected autobiographical narratives by Yi Sŏkhun, Yi Kwangsu, and Ch’ae Mansik, each of whom reckoned with their past acts of collaboration through painful self-reflection. The chapter focuses on the distinctive literary devices used to interrogate the complexity of collaboration and the consequences of the Special Investigative Committee for Anti-National Acts. Chapter Three also deals with autobiographical writings, examining two versions of Yi T’aejun’s autobiographical fiction and the role of state pressure on the representation of collaboration and resistance. The chapter explores Yi’s struggles with the DPRK’s strict literary policies. Chapter Two and Four illuminate the literary reactions of South Korea’s canonical writers to the increasing ideological rigidity of the Cold War. Yŏm Sangsŏp, the key novelist examined in Chapter Two, criticizes the supplanting of the Japanese empire with the U.S. occupation, and poses the act of crossing the thirty-eighth parallel as a way to imagine the space beyond the border. By analyzing the lesser-known novels of Kim Tongni and Yi Kwangsu, Chapter Four traces how these writers aimed to accommodate, but failed to embody, the state-implemented anticommunist themes in their literature. Postliberation literature provided a reflective space for interrogating collaboration, while challenging political polarization. In their literature of decolonization, postcolonial writers refute the imposition of the Cold War ideology, and thereby, postpone it for those five years.