The Hundred Years War had substantial influence not only on the age of Chaucer but also on Chaucer himself. Chaucer fought against the French during the War and was taken prisoner and held until ransomed by King Edward II of England . While a prisoner, he completed his first literary work, The Romance of the Rose, which he translated from French. The Canterbury Tales also contains several subliminal references to events surrounding the War, although it is not mentioned specifically:
- Chaucer's Knight occupies a prominent role in the Tales, and represents a model of medieval chivalry which still existed at the time of the War, although it faded shortly thereafter.
- The Wife of Bath's tale discusses the economic situation in England, which had suffered as a result of the war.
- The Black Death, religious corruption, and political intrigue are mentioned at various parts of the Tales.
It would thus appear that the Hundred Years War had a significant effect on the writing of Chaucer.
Aside from the numerous military implications of the conflict, England experienced a great deal of change that was either caused or exacerbated by the Hundred Years War. One significant social change was actually connected to changes in tactics on the battlefield. Because of the advent of the longbow, and eventually gunpowder, the heavily armoured knight on horseback became obsolete. The nobility from which these knights were drawn declined in political importance accordingly, especially in England. This change was also accompanied by the end of serfdom, a product of both the war and the demographic change occasioned by the Black Death.
The war also saw the rise of nationalism (and, indeed, the rise of a nation-state) in England. It marked the final stage in the evolution of England as an Anglo-Norman kingdom to one with a sense of its own "Englishness." Court French declined as a language of the nobility in England, and accordingly as a literary language. The war also featured an unprecedented propaganda blitz, as the crown attempted to portray the French as bloody brutes bent on murder.
The increasing power of the monarch led to a discourse of liberty in England, one which emphasized fair taxation, distrust for a standing army, and the corruption of royal ministers. These ideas were expressed in petitions to the king from rebels led by Wat Tyler, whose rebellion in 1381 was launched in response to a poll tax.