In the world of children's literature, analyses of the distribution and representation of gender, biological sex, and gendered behavior in picturebooks often focused on Caldecott Award-winning literature. As the most prestigious award for American children's picturebooks, titles that receive this honor have a profound influence on the field of children's literature: Caldecott Medal and Honor books are ordered by nearly every school and public library in the United States. In this study, the authors build upon and extend previous research on Caldecott Award-winners by critically examining constructions of gender across all 74 Caldecott Medal-winning picturebooks, from the inception of the award through the current award-year (2011). While some authors of prior studies of Caldecott winners explored titles across multiple decades, the majority examined Medal and/or Honor books across only a short span of time. Some of these authors also included literature beyond Caldecott Award-winners in their samples, such as Little Golden Books or recipients of the Coretta Scott King or Newbery Awards, with many concluding that picturebooks which receive the Caldecott Medal are "clearly less stereotyped than the average book, and do not include the most blatant examples of sexism". As a result, the authors focus in this study solely upon Caldecott Medal-winning titles and constructions of gender within this collection of popular and influential books. (Contains 1 footnote.)