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This article examines a strand of social and cultural thinking in the twentieth century that has its roots in casuistry, or engaging our conscience in everyday life. Despite their connections, little has been written about the relations between the work of Max Weber, R.H. Tawney, and Richard Hoggart. The article endeavors to address this gap in scholarship by conceptualizing the interrelatedness of their writing under the term “left-wing conscience.” While the dominant moral strand of left-wing politics in the twentieth century went under the label, ethical socialism, the term does not describe the positions of all the thinkers in this tradition nor does it emphasize what connects them. Rather, the concept of “left-wing conscience” foregrounds the casuistic nature of their writing where they inscribed conscience at the center of their politics rather than, as many left-wing radicals of the century were tempted to do, placing politics at the center of their conscience. Moreover, when conscience is modified by left-wing, it highlights the progressive and reformist focus of these writers. It was this progressive conscientiousness that led each of them to value the development of personality and the capacity for judgement and to analyze how these were being eroded throughout the century. What this article brings to light is how Weber initiated a line of sociological writing grounded in moral seriousness. This was picked up by Tawney and amended with an explicit left-wing politics. These strands were, then, synthesized by Hoggart, who brought them into his cultural criticism in order to respond to the issues of relativism in the culture of the latter half of the century.