In his autobiography, Little Did I Know, the Harvard philosopher Stanley Cavell traces the roots of his philosophical approach to his childhood, examining what he had to learn to make sense of his father’s anger at the world and at him. Cavell describes the huge shadow his father cast over his work, even as Cavell himself achieved success in an academic sphere “quite beyond comprehension” for his uneducated father (Little Did I Know, p.356). This chapter will begin by considering Cavell’s account of his relationship with his father, and what it was that he learnt about doubt and acknowledgement in making sense of his father’s hate. The next section will outline the main current of Cavell’s philosophical work: his thinking about what is at stake in scepticism regarding the pain of others. The powerful implications of his reflections on this issue will then be demonstrated through attention to Cavell’s work on Shakespeare, with particular attention to themes of attachment and doubt in King Lear.