In terms of English history, the time span between the collapse of the Roman Empire and the Renaissance is called the Middle Ages, and the adjective "medieval" refers to whatever was made, written, or thought during the Middle Ages. The Middle Ages was a period of enormous historical, social, and linguistic change, despite the continuity of the Roman Catholic Church.

The Anglo-Saxon invaders, who began their conquest of southeastern Britain around 450, transcribed and transliterated works into Old English. Linguistic and cultural changes in Britain were accelerated by the time of the Norman Conquest in 1066, when words from French began to enter the English vocabulary. Until the close of the fourteenth century, French was the language of conducting business in Parliament and in a court of law. Awareness of a uniquely English literature did not actually exist until the end of the war begun by Edward III in 1336 to enforce his claim to the French throne. Geoffrey Chaucer's decision to emulate French and Italian poetry in his own vernacular prompted a changed in the status of English.

Britain was largely Christian during the Roman occupation. After the collapse of the Roman Empire, peoples belonging primarily to three Germanic tribes invaded Britain: the Angles, the Saxons, and the Jutes. Christian missionaries were sent from Kent in southern England and from Ireland to consolidate religious control of Britain. The conversion of the people was completed in 731, according to Bede's Ecclesiastical History of the English People. Before the Christian conversion, there had been no books. Anglo-Saxon heroic poetry was part of an oral tradition. The Beowulf poet and other Christian writers were fascinated with the conflict between the heroic code of their pagan ancestors, which stressed blood revenge, and the Christian religion's emphasis on forgiveness. Formulaic phrases, irony, and harsh struggles characterize Old English poetry.

The Normans, an Anglo-Saxon tribe of Germanic ancestry whose name is a contraction of "Norsemen," conquered England in the Battle of Hastings. They adopted the French language and Christian religion of the land. Henry II, the first of England's Plantagenet kings, acquired vast provinces in southern France through his marriage to Eleanor of Aquitaine, the divorced wife of Louis VII of France. Linguistic and cultural exchange characterized the period of a French-speaking ruling class in England. Latin remained the "international" language of learning, theology, science, and history. The Norman aristocracy spoke French, but intermarriage with native English nobility and everyday exchange between masters and servants encouraged bilingualism. Celtic languages were spoken in Ireland, Wales, Cornwall, and Brittany. Many literary texts written in Anglo-Norman England were adapted from French and Celtic sources.

The growth of international trade and influence of the merchant class came amidst calamities and upheavals of the fourteenth century. To finance his wars, Edward III was obliged to negotiate for revenues with the Commons in the English Parliament, allowing the institution to replace the church as a major political force. The linguistic, political, and cultural climate in Britain by the 1360s allowed for a "flowering" of Middle English literature in the writings of Geoffrey Chaucer, William Langland, and the Gawain poet. Chaucer drew from the work of ancient Roman poets, yet he never achieved the laurels accorded to Petrarch during his own time. William Langland, author of Piers Plowman, presented a clear-sighted vision of social and religious issues in his writing. In the fifteenth century, morality plays personified the vices and virtues as they struggle for the soul of "mankind" and "everyman." Julian of Norwich and Margery Kempe provided insights into the female perspective of the church and its doctrines. Sir Thomas Malory defined the English form of the sage of King Arthur and his knights in Morte Darthur.

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