This article examines the historical truth of the ‘pear of anguish’ – a common exhibit in European dungeon museums that has recently made its way into the popular imagination by way of TV shows and internet sites. Like the ‘chastity belt’ before it, the ‘pear of anguish’ evidences the ‘dark medievalism’ of the modern consciousness, a dystopian view of the Middle Ages that imagines pre-Reformation Europe as a nexus of cruelty and sexual perversion. The historical reality, however, traced here through commentaries and catalogues from the past few centuries, would seem to indicate that both the device itself and its imagined function are creations of the modern world.