The article addresses ways critics and practitioners can identify and make use of “representational conundrums” to explore multiple and complex issues surrounding the phenomenon of disability in the analysis of drama and live performance. The author defines the term representational conundrum to describe the ways in which disability uniquely confounds meaning in cultural production. The argument is that critics tend to reconcile paradoxes by supplying go-to answers to puzzling questions and then passing judgment on them. Through examples, the article offers reading strategies of dramatic texts that maintain the generative and powerful potential of the unsolved conundrum, a potential that can be mined as text moves to production.