Sometime around the year 1630, Artemisia Gentileschi, a famed Baroque woman artist, painted one of her most intriguing masterpieces, the stunning Self-Portrait as the Allegory of Painting. As a personal statement, the image has been unrivaled to this day, its daring symbolic formula unmatched by any other artist past or present. The focus of this thesis is to define the interactions between Artemisia's Self-Portrait and self-portraits of sixteenth century women artists, most notably Sofonisba Anguissola and Lavinia Fontana. In this manner, the extraordinary implications of Artemisia's Self-Portrait become even more pronounced. Likewise, the thesis also explores instances of "countering culture" in the works of sixteenth century women artists, highlighting moments when their own self­images progressed beyond the normal bounds of social definitions. Finally, the essay explores the possible symbolic meanings of Artemisia's Self-Portrait within the realm of the court of Charles I of England, its initial owner.