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This essay is a study of the ancient Greek story of ”Hero and Leander” as a subject in visual art. It examines the subject’s iconographical representation, from its first depiction during antiquity to circa 1900, in order to discern how it evolves over time and what the contributing factors to this evolution is. Seven main categories of how the subject is represented could be determined. One work in every category was chosen as representative and examined closer using Erwin Panofsky’s iconographical method. The results show that three main factors affect the way “Hero and Leander” is depicted: the literary sources the artists had available, the material context concerning the artwork’s production and the cultural context the artwork was created in.