A few days into the new school year, the author's female students invariably beg, plead, and cajole her in the hopes of watching Disney's "Pocahontas" in class. Toddlers when the film was released in 1995, doubtless they have seen it already dozens of times; more importantly, the author cringes at the ethnic and gender stereotypes sometimes promoted by the animated "classics." This year, however, rather than summarily dismiss the girls' request, she honored it. She used their admittedly flawed knowledge of Pocahontas as a springboard to dive more deeply into 17th-century politics and culture in England and the Chesapeake. By contrasting the images of the Powhatan princess that they had imbibed as children with those commissioned by Pocahontas herself, the author was also able to inaugurate a year-long series of critical thinking exercises with images. In this essay, the author will detail the sources and the questions that she used to develop the Pocahontas exercise, and suggest ways that teachers might develop similar exercises for their own classes. Moreover, she will provide a pedagogical rationale for incorporating various types of visual stimuli into an introductory survey of United States history at the secondary and post-secondary levels. Finally, she appends an annotated bibliography of traditional and digital sources for teachers and students alike. (Contains 7 figures and 10 notes.)