This article looks at the semantic polarities fear and courage, good and evil, in the work of Phillip Roth. It looks at a number of Roth's novels, in particular, Nemesis and The Dying Animal, Exit Ghost and The Humbling, suggesting how societies received ideas of what is morally acceptable contrast with the protagonist's need for a freedom, particularly sexual freedom, but also freedom of expression, both of which are seen as transgressive. The article goes on to suggest that while this dynamic remains essentially intact throughout Roth's work, the various elements in it shift with the age of the protagonists, and the age of Roth himself.