Portraiture reflects how the concept of individuality has changed throughout history. While in the fifteenth century portraits primarily focused on the social status of the represented person, in the following centuries, individuality and personality became more important. Fast forward to the twentieth century, however, and portraiture began to question these conventional concepts of individuality and subjectivity. This seminar will investigate the portraiture from the “invention” of the individual in fifteenth-century Italy to its “deconstruction” in the twentieth century. We will discuss these developments in front of the originals in the collections of New York City museums, including the Metropolitan Museum and the Museum of Modern Art.