This essay is composed of two distinct but related parts. The first considers how the title of Joyce's first novel invites analogies with the tradition of the “self-portrait as a young man” in the history of painting, notably in the work of Dürer, Rembrandt, and Van Dyck, each of whom made a series of youthful self-portraits. These analogies are considered on both formal and theoretical levels. The second part of the essay considers the history of portraits of Joyce made by other artists. Although such portraits are as varied as Joyce's writings, they can be loosely divided into two categories. On one hand are those which establish Joyce's image as that of an eminent man of letters. On the other hand are those which transform Joyce's image into a figure of the avant-garde, where literature and the visual arts are understood as being part of a common project. The stories of how these latter works came to be made give evidence of Joyce's engagement with contemporary visual art as being like his own work in its formal experimentation. Both kinds of portrait, traditional and avant-garde, reflect Joyce's construction of his own image, as well as the manner in which the artistic modes of the twentieth century evolve along with those of Joyce's work.