This thesis examines the way in which the characters of the Grimm Brothers' "Rapunzel" change and shift through different adaptations of the fairy tale. Focused on the contemporary adolescent novels Rapunzel's Revenge, Golden, and Zel, this thesis looks at the ways in which Rapunzel, the witch, and the prince transform from characters that lack depth in the fairy tale into fully developed characters that represent modern feminist and American conceptions of gender roles. In each adaptation being examined, the new contexts into which the tales have been written result in significant changes to the representation of the primary characters of the story. Authors of contemporary fairy tale adaptations change, shift, and build on the traditional tales' ingrained networks of symbols, figures, and archetypes to create stories that can not only span a full-length novel, but can also be adjusted to fit a contemporary audience. The characters shift to fit the new molds made by the shifts in the ideological stances the authors of the texts hold as significant; they are representative of the authors' imposed context, the context that represents their ideologies (the collection of ideas that make up the author's conception of the world, whether knowingly or unknowingly), agendas (the ideas that the author is knowingly inserting into the text), and connections to the story of "Rapunzel." This thesis tracks these changes and identifies the way these shifts work within the text, and within the larger context that the text was written in. In the end, this text demonstrates the method in which fairy tales stay relevant to a society that is very different than the one they were recorded in; it shows how changes made to the fairy tale represent fundamental and traceable changes in the culture the adaptation was written in.