Toria Johnson interrogates the classification and portrayal of compassion in two major texts: the anonymous morality play Everyman (c. 1508) and Shakespeare’s King Lear (1606). Taking these plays as examples of pre- and post-Reformation approaches to compassionate interaction, she scrutinises a noticeable shift in attitudes towards the idea of pity, both as a fundamental human trait, and as an organising principle for human interaction. Whereas pre-Reformation plays like Everyman stress the volatility and unreliability of an emotion like pity – preferring instead the more established structure offered by charity – King Lear imagines a world without charity, and without the Church as an overseer of interpersonal exchange. Lear, she argues, reflects an emotional response to the Protestant revision of medieval penitential culture, and in so doing, Shakespeare imagines the possible consequences of England’s new emotional landscape. This chapter examines how the language, structure and ceremony of ‘compassion’ changed in the wake of the English Protestant Reformation, and how these shifts altered the way people experienced or understood the compassion of their communities.