This chapter details a case study of a librarian and high school English teacher who collaborated on Shakespeare projects to improve students’ critical reading of sonnets and soliloquies. The literary analysis goal expanded as students developed media-rich products that reflected media literacy skills: performing advanced searches, locating research to inform image selection of primary sources, and evaluating images to communicate analysis of Shakespeare works. Students also modeled digital citizenship skills by respecting the copyright of images, and exploring contemporary images from creative commons sites. Following fair use guidelines, students created transformative works, adding value to and repurposing copyrighted materials. Text, images, and music were combined into a movie using the free digital software Animoto. The school librarian and teacher successfully collaborated, supporting goals of improving literacy and helping students to become 21st century learners.