Criticism of the Shakespearean canon through adaptation as a genre has the capacity for liberation and social reparation. As a cluster of complex texts that sustains both past practices and contemporary interpretive conventions, Shakespeare provides fertile ground for training students to listen intently and compassionately to other individuals’ voices. This chapter theorizes contextualized and interactive pedagogies that link historical texts to our contemporary contexts. Contextualization enables students to find their own voices. Interactivity nurtures student-initiated engagement. Education can be reparative when we practise ‘radical listening’: a set of proactive communication strategies to listen for the roots rather than only the ‘plots’ of stories.