Jacques Derrida’s theory of deconstruction provides an ideal means of appreciating and interrogating the duality central to both Robert Louis Stevenson’s Strange Case of Dr Jekyll and Mr Hyde and its adaptations. Moreover, because deconstruction exposes binary oppositions as artificial and constrictive, it enables us to advance beyond them toward multiplicity, a term used by Gilles Deleuze for a complex, ever-changing, multipart structure that transcends unity. Roy Ward Baker’s Dr Jekyll and Sister Hyde (1971) and episodes of Showtime’s Penny Dreadful (2014–2016) offer fresh ways to think about—and beyond—the duality of culture’s most famously divided pair. The binary oppositions that organize each text are innovative, as are the ways in which these oppositions are reversed and conflated. Ultimately, these adaptations employ triangulation to deconstruct themselves, thereby demonstrating the limitations and instability of duality, as well as the possibilities of multiplicity.