When it premiered in 1953, Playboy Magazine challenged norms of gender and sexuality in America. It included articles of current events, social and political columns, and comics which were all wrapped together with centerfolds of naked women. Playboy became the leading men’s entertainment magazine for decades and has been praised for sexually empowering women and criticized for exploiting them. This thesis is a case study of the representation of women in Playboy over three significant cultural moments in time. The first moment is the 1950s, when the magazine premiered during a decade that discouraged displays of sexuality for women. The second moment is the late 1960s to early 1970s, when second-wave feminism began to critique the contents of Playboy magazine as dehumanizing rather than liberating. Finally, the third moment explores Playboy magazine and the reality TV show The Girls Next Door in the 2000s, and how it reinvented an image of women that was synonymous with raunchy trends of the time. I make the case that Playboy promoted its brand as a fantasy that both men and women were excited to partake in. However, those who were involved with the brand experienced exploitation and disillusionment behind the scenes.