This article discusses how to make the classics matter to students through digital literacies and essential questions. The authors share their experiences with planning and delivering a unit that ultimately gave "The Scarlet Letter" real meaning for their students--and helped them do the same for other classics they taught. Students read "The Scarlet Letter" with enthusiasm when the teachers tied it to questions about risky behavior and a multimedia project. By finding essential questions for these classics that both evoked strong interest from the students and allowed deep exploration of the novel, and by creating assessments that sprang from those essential questions and tapped student interest, the authors were able to invite students to have meaningful experiences with these works. (Contains 1 figure.)