Introduction The nature of art extends to almost every aspect of the human experience. Life, death, emotions, experiences, and even such concepts as gender and sexuality are often seen in various works of literature, music, and cinema. Often these themes and topics are represented through the beliefs and ideas of the author. One such work is the collage novel by Max Ernst titled “The Hundred Headless Woman.” The novel is highly interpretive but has strong themes of gender and sexuality. This paper will examine the gender and sexual themes of the novel by utilizing the gender concepts outlined by Eve Sedgwick. Gender Theory and Queer Theory To fully understand the views of Eve Sedgwick on these themes, a brief explanation of the theories related to them, as well as their history is required. These topics have been examined many times throughout the years, but only recently have they become represented in the mainstream discourse. Two types of theories are related to this discussion: gender theory and queer theory. Donald E. Hall refers to the term “gender theory” like this: “though commonly used, the term “gender theory” is something of a misnomer or, at best, a euphemism” (107). His issue with the term is that in reality it mostly focuses on the critical examination of the identity politics of sexuality. Therefore, he suggests that a correct term would be “sexuality theory.” Raymond Williams describes the original meaning of the word “sex” like this: “in its early uses it is a description of the division between them [the sexes]” (283). He describes the meaning of sexuality in two ways: a scientific one that refers to the spermatozoon and a more casual one that refers to people (Williams 285). The original meaning of these words accurately represents the term “sexuality theory” proposed by Hall. It is important to note that the gender theory has its roots in the feminist theory’s analysis of gender roles. However, its focus on sexuality differentiates it from the feminist theory and leads to different ideas. Gender theory is not a recent phenomenon. Although the term “gender theory” has not been used in centuries past, every era had its gender theory that evolved over time. An idea of the era’s gender theory can be gained from an analysis of its art. Classical literature especially can be representative of this because it survived throughout the years and established itself as an important piece of art (Hall 107). For example, classical Greek poetry was often focused on the beauty of youth and the desire for intergenerational relationships. Ancient Greece had a strong culture of tutelage between adults and young boys. Adults would provide education for the boys while getting emotional and physical affection in return. The sexual nature of this affection is often debated, but the culture of the time supports this notion (Hall 107). Other works suggest that heterosexuality and homosexuality were looked upon equally, and without judgment. Later, due to the increased influence of Judaism and Christianity, these ideas slowly changed over time (Hall 108). Currently, Western art is slowly transitioning from treating homosexuality, lesbianism, and transsexuality as taboos to putting more foc