In the seventeenth century, Dutch and Flemish artists presented a strange new face to the public in their self-portraits. Rather than assuming the traditional guise of the learned gentleman artist that was fostered by Renaissance topoi, many painters presented themselves in a more unseemly light. Dropping the noble robes of the pictor doctus, they smoked, drank, and chased women. Dutch and Flemish artists explored a new mode of self-expression in dissolute self-portraits, embracing the many behaviors that art theorists and the culture at large disparaged. Dissolute self-portraits stand apart from what was expected of a conventional self-portrait, yet they were nonetheless appreciated and valued in Dutch culture and in the art market. This dissertation explores the ways in which these untraditional self-portraits functioned in art and culture in the seventeenth century. Specifically, this study focuses on how these unruly expressions were ultimately positive statements concerning theories of artistic talent and natural inclination. Dissolute self-portraits also reflect and respond to a larger trend regarding artistic identity in the seventeenth century, notably, the stereotype "hoe schilder hoe wilder" that posited Dutch and Flemish artists as intrinsically unruly characters prone to prodigality and dissolution. Artists embraced this special identity, which in turn granted them certain freedoms from social norms and a license to misbehave. In self-portraits, artists emphasized their dissolute nature in self-portraits by associating themselves with themes like the Five Senses and the Prodigal Son in the tavern. These playful, inventive and sometimes challenging self-expressions present a unique vision that broadens our perception of what it meant to be an artist in the Dutch Golden Age.