Despite ongoing and prolific critical scholarship arguing for the widening of the secondary language arts curriculum, many practicing teachers are required or encouraged to teach a curriculum dominated by canonical texts. This is often the case at schools with highly diverse students whose varied cultural and linguistic backgrounds have historically been silenced by traditional forms of language arts instruction. In this article, the authors critically reflect on their collaborative attempts across multiple years to decenter and destabilize a required 10th grade unit on a Shakespearean play. They describe a shift in focus from a unit originally centered on traditional literary analysis of "Hamlet" to a unit rooted in discussions of how power and privilege operate across varied texts. Describing their use of the graphic novel "Yummy" to complicate understandings of "Hamlet," the authors discuss how an emphasis on critical reading and critical multimodal composing across both texts allowed them to reflect on and challenge their own teaching practices. The authors then conclude with an acknowledgment of the risk, flexibility, and reflection needed to do this kind of critical work in canonically-centered classrooms.