This article discusses how literacy and literature goals merged in a media project designed to encourage high school students to build new connections with the poetic elements of Shakespeare's plays "Romeo and Juliet" and "Julius Caesar." Using the free software Animoto movie maker, students were challenged to look closely at Shakespeare's words and imagery to dramatize a character through selection of text, imagery, and music. The Shakespeare digital movie project hoped to address literacy concerns such as students' lack of curiosity, reluctance to engage in analysis, and focus on skills rather than communication, and build essential skills for success in college: developing curious minds and an ability to analyze and synthesize ideas to communicate insights with an audience.