The Hundred Years War (1337-1453) was one of the longest military engagements of the middle ages, and one of its most significant. Yet while the conflict’s political, military, and socio-cultural aspects have been well-studied, the literature composed during the period has not. Thus, this thesis attempts to fill a gap in the scholarship of the Hundred Years War by analyzing the literature directed at four of the five successive English kings who took part in the conflict – Richard II, Henry IV, Henry V, and Henry VI (c. 1377-1453) – by way of manuscript dedications, addresses, and gifts.