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Selfie-photography is generally thought of as a cultural mass phenomenon of the early 21st century, inseparably related to the development and triumph of the smartphone with integrated camera. Western culture, however, has been highly familiar with self-depictions since the Renaissance days. Putting the contemporary selfie into this historic context covering more than five centuries of cultural development from Dürer's (1500) famous “Self-Portrait at 28” (also known as “Selbstbildnis im Pelzrock”) to today's Instagram galleries allows for identifying central parallels concerning the technical and social antecedents as well as common underlying psychological factors and shared properties of different kinds of self-depiction. The article provides an overview of the types of contemporary photographic selfies and compares them with painted self-portraits. Finally, this historic perspective leads us to the insight that self-portraits as well as selfies are both referring to nothing less than the “conditio humana.”