Children learn behaviors through media examples, including behaviors tied to gender. Girls can be presented as domestic and passive; boys are seen as adventurous and active, with reinforcement even in Newbery Medal-winning books for children. Past studies discovered the discrepancy between male and female roles in Newbery Medal winners, but none have been updated since 1998. This project analyzed gender roles and stereotypes in Newbery Medal winners from 1998 to 2009. Within the theoretical framework of sociologists Charlotte Perkins Gilman, Candace West, and Don Zimmerman and educational theorist Paulo Freire, this study examined the number of well-developed and total characters in each book. In addition, it used Perry Nodelman's home/away/home model of children's literature to focus on critical points in the narrative and assess each protagonist through descriptions, actions, and dialogue. Common themes emerged pointing to the evolving roles of male protagonists and the static, traditional roles to which female protagonists are relegated. This study is essential in beginning to understand the complexity of the creation and reification of gendered stereotypes through literature.