How can teachers build students' interest and engagement in reading texts in the high school English curriculum while still providing access to challenging texts from the canon? Teachers typically expect their secondary students to read texts from the English canon because these texts offer opportunities for meaningful reflections on essential questions. However, students often do not or will not read these texts because they find them boring or they reject the directive manner in which teachers present the texts to them. To address this challenge, the authors offer Linked Text Sets (LTS; Wold et al.) as multiple entry points to scaffold students' examination of essential questions connected to canonical texts. Linked Text Sets provide a strategic means for using texts from both adolescent literature and the literary canon that foster students' thinking about their own identity and the process of becoming adults.