This paper suggests that Shakespeare’s plays offer an embryonic version of criminology, and that they remain a valuable resource for the field, both a theoretical and a pedagogical resource. On the one hand, for criminology scholars, Shakespeare can open up new avenues of theoretical consideration, for the criminal events depicted in his plays reflect complex philosophical debates about crime and justice, making interpretations of those events inherently theoretical; reading a passage from Shakespeare can be the first step in building a new theory of criminology. On the other hand, for criminology students, Shakespeare can initiate and sustain an intellectual transition that is fundamental to their professionalization, namely the transition from what I call a “simplistic” to a “skeptical” model of criminology. For this reason, I recommend that criminologists try what the Shakespearean scholar Julia Reinhard Lupton has called “thinking with Shakespeare.” Thinking with Shakespeare is particularly valuable for criminologists because Shakespeare coded ancient philosophical ideas about crime and justice into the words and deeds of his characters: interpreting the drama takes us into the philosophy, and the philosophy provides us with the conceptual equipment for a better criminology.