As the genre of farce more generally, Shakespeare’s early farce The Comedy of Errors is often dismissed as superficial because of its farcical elements, or its farcical nature is downplayed by well-meaning critics. In this essay, I argue that it is precisely in its farcical superficiality that the play unfolds sceptical philosophical potential. Employing concepts developed by Ludwig Wittgenstein and Stanley Cavell, I try to show how this farce, in comically unsettling the very foundations of human language, culture and identity, gestures at uncomfortable truths about the fundamental conventionality of human nature and society.