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THE AUTHOR AND HIS TIMES
Most people in the English society of Chaucer's time, about 600 years ago, viewed the world in a similar way and accepted the same beliefs. People then believed that behind the chaos and frustration of the day-to-day world there was a divine providence that gave a reason to everything, even though that reason wasn't always obvious. When you've got faith in an overall system like that, it's easier to accept and understand the world around you. People in Chaucer's society could feel, at least much of the time, a sense of security about the world, knowing that it was following a divine plan. They trusted the system they believed in; it was true, and they felt no need to question it.
So behind all of Chaucer's satire and social put-downs in the Canterbury Tales is an unshaken belief in a divine order. It's easier to make fun of something when, underneath, you know you take it seriously. Also, as Chaucer knew, it's easier to write for a group of people who at least roughly share the same set of values, whether they be a cook, a parson, or an upper- class prioress.
Those values were represented in the medieval world by two structures: the class system and the church. People believed both setups were established by God, and each went unchallenged. A peasant, like Chaucer's Plowman, wasn't "upwardly mobile" as in our society, and didn't aspire to become a knight. He may want to buy more horses or farm more land, but he wouldn't change his basic lifestyle or his station in life.
In the Middle Ages, each person was classified according to his or her "estate" or place on the social scale depending on birth, profession, and other factors (such as whether a woman was married-an important discussion of which is in the Wife of Bath's Tale as well as others). Each social grouping was like a symbol of the divine order, as immune to change as the hierarchy of angels. That's why a move from the peasant to the middle class, for example, was almost unheard of.
The middle class was in its infancy then. Chaucer himself was a member of what we'd call the upper middle class; he got jobs at court without actually being royalty. He started out as a page, serving meals and learning the ropes of becoming a courtly gentleman. He also quickly found out about the conflicting whims of human nature and the importance of the right appearances, both lessons he draws on in the Canterbury Tales. He evidently learned them well in real life, too, because he became a diplomat and traveled for the king to France and Italy, where he picked up plenty of literary influences that show up in the Canterbury Tales and other works.
Chaucer uses class structure very clearly in the Tales, presenting the Knight first and having him tell the first tale because he's the highest-ranking pilgrim present. The nobility, being at the top of the social scale, was responsible for cultivating virtue, keeping the peace by maintaining social order, and setting a moral example for the other classes to follow.
Apart from the worldly order but just as important was the church hierarchy. It, too, was a structure ordained by God (especially since everyone in the church was Roman Catholic in the hundreds of years before Martin Luther and the Reformation). Yet within the church ranks there was incredible in-fighting between the "regular" clergy (those in convents and monasteries, like the Monk, Prioress, and Friar in the Tales) and the "secular" clergy (parish priests like the Parson and eventually perhaps the Clerk). Each section was, in a sense, feuding with the other for "turf." Chaucer exemplifies this by showing an argument between the Pardoner (a church official of the secular variety) and the Friar, who is in direct competition with the Pardoner for money and religious influence over the parish villages they both travel through.
The regular clergy, in particular, had a reputation for corruption at that time. Monasteries, which were supposed to be apart from the world and whose inhabitants were to avoid worldly goods, were almost as lavish as castles by the 14th century, and most people assumed that friars (like Chaucer's picture of one) kept much of the money they were supposed to give to the poor. At one point in his life Chaucer lived in a part of London that was very near several large monastic orders, and he probably got to see a good deal of their life and work. He also, as we can see from his portraits, had little sympathy for cheating clerics. In fact, he was once fined for beating up a friar outside a courthouse!
Yet people still gave money to friars and pardoners because you could never be too sure. Even if the friar or pardoner were corrupt, giving to charity or buying a papal pardon could still help get you into heaven or at least knock a few thousand years off your stay in purgatory. Also, just because a friar or monk was a less-than-sterling example of his station, the social position itself still commanded respect.