This chapter provides a brief overview of the development of crusading practices in Europe from the eleventh century until their formal end in the seventeenth. It highlights crusading’s broad impact on society, its inconsistent racial and religious discrimination, and the appeal of its story of loss and recovery across social levels. The chapter then discusses two popular Middle English romances, Richard Coeur de Lion (c. 1300) and Guy of Warwick (c. 1330), to illustrate the ways crusading affected and was affected by literary narratives. The two poems represent different kinds of crusading practices – the large army sponsored by ecclesiastical authorities and the individual undertaking a personal vow without church involvement – while offering critical commentary on crusading itself. These crusading romances and others like them situate the British Isles as part of a larger premodern world engaged in religious conflict and exchange. By recognizing the long relationship between the romance and holy warfare – one that lasted well into the early modern period – we can better understand the interests of medieval and Renaissance audiences as well as the foundational role of religious intolerance in modernity.