This article investigates Lin Yutang’s (林語堂) bilingualism and cosmopolitanism under different circumstances to further the current discourse on dynamic language equivalences and culture-crossing. Different from previous critical works, this study covers Lin’s major self-translated works from distinctive historical periods, Zi jian Nanzi/Confucius Saw Nancy (1928/1929), “A Hymn to Shanghai”/“Shanghai zhi ge” (1930/1933), and Between Tears and Laughter/Ti xiao jie fei (1943/1943), by examining the publishing environment into which these works entered, the historical contexts that drove him to self-translate, the various translation methods he adopted for specific situations, and the manifold changes he made with the shifts of skopos. The study brings to light a tendency of self-translators to revise their originals, which allows their works to benefit from the insights gained in self-translation, and contends that Lin’s contribution to translation studies is much greater than is generally believed in academia.