Where do our most cherished teaching principles derive? How do we deploy them in ways that motivate students and nurture their critical engagement with the wider world? Drawing on insights gleaned from the film Bill and Ted's Excellent Adventure, this reflection explores how the development of two key strategies—engaging students through blended academic and pop-culture approaches and guiding their recognition and critical response to discursive power structures—transformed the author's pedagogical approach into one that is more student-centric and practically focused. Developed in the context of political science courses, but applicable especially to English and its instruction, these strategies decenter the instructor to promote more authentic engagement between students and the content they encounter, as well as with each other and the instructor. The strategies themselves, however, derive from a recognition that even the most light-hearted fare (such as Bill and Ted) may offer thoughtful insight into the craft of teaching: first, by recognizing that joy, passion, and creativity matter when structuring engaging learning experiences; and second, by clarifying how our attunement and response to subtle exercises of power—in the case of the film, pedagogical norms around acceptable academic projects—are instrumental in navigating a complex world.