In 1386, Chaucer became Controller of Customs and Justice of the Peace and, in 1389, Clerk of the King's Works. It was during these years that Chaucer began working on The Canterbury Tales.
The end of the fourteenth century was a turbulent time in English history. The Catholic Church was in the midst of the Western Schism and, although it was still the only Christian authority in Western Europe, it was the subject of heavy controversy. Lollardy, an early English religious movement led by John Wycliffe, is mentioned in the Tales, which also mention a specific incident involving pardoners (sellers of indulgences, which were believed to relieve the temporal punishment due for sins that were already forgiven in the Sacrament of Confession) who nefariously claimed to be collecting for St. Mary Rouncesval hospital in England. The Canterbury Tales is among the first English literary works to mention paper, a relatively new invention that allowed dissemination of the written word never before seen in England. Political clashes, such as the 1381 Peasants' Revolt and clashes ending in the deposing of King Richard II, further reveal the complex turmoil surrounding Chaucer in the time of the Tales' writing. Many of his close friends were executed and he himself moved to Kent to get away from events in London.
While some readers look to interpret the characters of The Canterbury Tales as historical figures, other readers choose to interpret its significance in less literal terms. After analysis of Chaucer's diction and historical context, his work appears to develop a critique of society during his lifetime. Within a number of his descriptions, his comments can appear complimentary in nature, but through clever language, the statements are ultimately critical of the pilgrim's actions. It is unclear whether Chaucer would intend for the reader to link his characters with actual persons. Instead, it appears that Chaucer creates fictional characters to be general representations of people in such fields of work. With an understanding of medieval society, one can detect subtle satire at work.
The Tales reflect diverse views of the Church in Chaucer's England. After the Black Death, many Europeans began to question the authority of the established Church. Some turned to lollardy, while others chose less extreme paths, starting new monastic orders or smaller movements exposing church corruption in the behaviour of the clergy, false church relics or abuse of indulgences. Several characters in the Tales are religious figures, and the very setting of the pilgrimage to Canterbury is religious (although the prologue comments ironically on its merely seasonal attractions), making religion a significant theme of the work.
Two characters, the Pardoner and the Summoner, whose roles apply the Church's secular power, are both portrayed as deeply corrupt, greedy, and abusive. Pardoners in Chaucer's day were those people from whom one bought Church "indulgences" for forgiveness of sins, who were guilty of abusing their office for their own gain. Chaucer's Pardoner openly admits the corruption of his practice while hawking his wares. Summoners were Church officers who brought sinners to the Church court for possible excommunication and other penalties. Corrupt summoners would write false citations and frighten people into bribing them to protect their interests. Chaucer's Summoner is portrayed as guilty of the very kinds of sins for which he is threatening to bring others to court, and is hinted as having a corrupt relationship with the Pardoner. In The Friar's Tale, one of the characters is a summoner who is shown to be working on the side of the devil, not God.
Churchmen of various kinds are represented by the Monk, the Prioress, the Nun's Priest, and the Second Nun. Monastic orders, which originated from a desire to follow an ascetic lifestyle separated from the world, had by Chaucer's time become increasingly entangled in worldly matters. Monasteries frequently controlled huge tracts of land on which they made significant sums of money, while peasants worked in their employ. The Second Nun is an example of what a Nun was expected to be: her tale is about a woman whose chaste example brings people into the church. The Monk and the Prioress, on the other hand, while not as corrupt as the Summoner or Pardoner, fall far short of the ideal for their orders. Both are expensively dressed, show signs of lives of luxury and flirtatiousness and show a lack of spiritual depth. The Prioress's Tale is an account of Jews murdering a deeply pious and innocent Christian boy, a blood libel against Jews that became a part of English literary tradition. The story did not originate in the works of Chaucer and was well known in the 14th century.
Pilgrimage was a very prominent feature of medieval society. The ultimate pilgrimage destination was Jerusalem, but within England Canterbury was a popular destination. Pilgrims would journey to cathedrals that preserved relics of saints, believing that such relics held miraculous powers. Saint Thomas Becket, Archbishop of Canterbury, had been murdered in Canterbury Cathedral by knights of Henry II during a disagreement between Church and Crown. Miracle stories connected to his remains sprang up soon after his death, and the cathedral became a popular pilgrimage destination. The pilgrimage in the work ties all of the stories together and may be considered a representation of Christians' striving for heaven, despite weaknesses, disagreement, and diversity of opinion.
Social class and convention
The upper class or nobility, represented chiefly by the Knight and his Squire, was in Chaucer's time steeped in a culture of chivalry and courtliness. Nobles were expected to be powerful warriors who could be ruthless on the battlefield yet mannerly in the King's Court and Christian in their actions. Knights were expected to form a strong social bond with the men who fought alongside them, but an even stronger bond with a woman whom they idealised to strengthen their fighting ability. Though the aim of chivalry was to noble action, its conflicting values often degenerated into violence. Church leaders frequently tried to place restrictions on jousts and tournaments, which at times ended in the death of the loser. The Knight's Tale shows how the brotherly love of two fellow knights turns into a deadly feud at the sight of a woman whom both idealise. To win her, both are willing to fight to the death. Chivalry was on the decline in Chaucer's day, and it is possible that The Knight's Tale was intended to show its flaws, although this is disputed. Chaucer himself had fought in the Hundred Years' War under Edward III, who heavily emphasised chivalry during his reign. Two tales, Sir Topas and The Tale of Melibee, are told by Chaucer himself, who is travelling with the pilgrims in his own story. Both tales seem to focus on the ill-effects of chivalry—the first making fun of chivalric rules and the second warning against violence.
The Tales constantly reflect the conflict between classes. For example, the division of the three estates: the characters are all divided into three distinct classes, the classes being "those who pray" (the clergy), "those who fight" (the nobility), and "those who work" (the commoners and peasantry). Most of the tales are interlinked by common themes, and some "quit" (reply to or retaliate against) other tales. Convention is followed when the Knight begins the game with a tale, as he represents the highest social class in the group. But when he is followed by the Miller, who represents a lower class, it sets the stage for the Tales to reflect both a respect for and a disregard for upper class rules. Helen Cooper, as well as Mikhail Bakhtin and Derek Brewer, call this opposition "the ordered and the grotesque, Lent and Carnival, officially approved culture and its riotous, and high-spirited underside." Several works of the time contained the same opposition.
Relativism versus realism
Chaucer's characters each express different—sometimes vastly different—views of reality, creating an atmosphere of testing, empathy, and relativism. As Helen Cooper says, "Different genres give different readings of the world: the fabliau scarcely notices the operations of God, the saint's life focuses on those at the expense of physical reality, tracts and sermons insist on prudential or orthodox morality, romances privilege human emotion." The sheer number of varying persons and stories renders the Tales as a set unable to arrive at any definite truth or reality.
The concept of liminality figures prominently within The Canterbury Tales. A liminal space, which can be both geographical as well as metaphorical or spiritual, is the transitional or transformational space between a "real" (secure, known, limited) world and an unknown or imaginary space of both risk and possibility. The notion of a pilgrimage is itself a liminal experience, because it centres on travel between destinations and because pilgrims undertake it hoping to become more holy in the process. Thus, the structure of The Canterbury Tales itself is liminal; it not only covers the distance between London and Canterbury, but the majority of the tales refer to places entirely outside the geography of the pilgrimage. Jean Jost summarises the function of liminality in The Canterbury Tales,
Both appropriately and ironically in this raucous and subversive liminal space, a ragtag assembly gather together and tell their equally unconventional tales. In this unruly place, the rules of tale telling are established, themselves to be both disordered and broken; here the tales of game and earnest, solas and sentence, will be set and interrupted. Here the sacred and profane adventure begins, but does not end. Here, the condition of peril is as prominent as that of protection. The act of pilgrimaging itself consists of moving from one urban space, through liminal rural space, to the next urban space with an ever fluctuating series of events and narratives punctuating those spaces. The goal of pilgrimage may well be a religious or spiritual space at its conclusion, and reflect a psychological progression of the spirit, in yet another kind of emotional space.
Liminality is also evident in the individual tales. An obvious instance of this is The Friar's Tale in which the yeoman devil is a liminal figure because of his transitory nature and function; it is his purpose to issue souls from their current existence to hell, an entirely different one. The Franklin's Tale is a Breton Lai tale, which takes the tale into a liminal space by invoking not only the interaction of the supernatural and the mortal, but also the relation between the present and the imagined past.