The Counterlife of Knight Errant Christie McKay is a novel about a man with two lives. Christie McKay is a middle-aged academic who has a self-harming partner he cannot leave. On a sabbatical studying Don Quixote he meets another woman and falls in love. However, instead of leaving his self-harming nemesis, he concocts an absurd fantasy that will allow him to lead a double life and have a relationship with both women at the same time. His attempts to compartmentalize both lives leads to tragedy as the one crashes into the other with dire consequences. The novel was partly inspired by Philip Roth’s notion of ‘the counterlife’, this being the double life that is created in order to make the official one somehow more manageable. Thus the rococo fantasies of a Billy Liar or, more commonly, the prosaic extramarital affair. The Trials of Philip Roth: Writing as Ordeal and Punishment examines the influence of a recurring trope in the writings of Philip Roth which I have called ‘The Trial’. I trace the development of this feature to a negative reaction to Roth’s early work, most notably the Goodbye Columbus collection of short stories and the novel Portnoy’s Complaint. The thesis examines the changing nature of this ‘trial’ conceit and how it is broadened and developed by Roth in the later works, especially in the so-called American Trilogy series of novels. I argue that the basic structure of the trial involves an individual, almost always a man, unjustly accused of some heinous crime by the presiding arbiters of moral taste. This individual is usually hounded and banished by their particular community. While acknowledging the complex differences between fiction and autobiography, I argue that Roth’s personal experiences of being on trial, in the earliest work for supposedly having ridiculed American suburban Jews, has helped to produce a body of work which feeds on rage and moral indignation and which repeatedly puts the individual up against a censorious community with suffocating concepts of normalcy.