In reference to The Canterbury Tales Prologue, what does it mean that Chaucer "provides amusement in ironic yet sympathetic observation of his fellows."
This expression, "provides amusement in ironic yet sympathetic observation of his fellows," means that although Chaucer points out the shortcomings of the other pilgrims' lives, thoughts, actions and beliefs, he does so with a sympathetic understanding of human failings. Irony shows how they are hypocrites and how they fail to do or be what they present themselves as doing or being, but Chaucer's sympathy keeps them from being repulsive.
A good example is in the Pardoner's description. Chaucer says of him that in order to look good, he rejects the clothing requirements of his religious order and does not wear the hood over his hair as he is supposed to do. Instead, he wore his yellow hair long, but unkempt, with only his religious skull cap on to represent the head coverings of his religious order.
This is ironic because since a Pardoner dispenses relics of forgiveness to (gullible) worshipers, we expect him to be holy and upright and care about worshipping according to the rules of his order. We find out, though, that he does not do what we expect. An event or trait that is something different from what is expected is ironic. Since his traits are presented by Chaucer's pleasant and lighthearted narrator, this irony is amusing.
There is more irony and it too is amusing. Later, we learn the Pardoner sings in church with great skill and can read a lesson or a story with equal skill:
He was in chirche a noble ecclesiaste;
Wel koude he rede a lessoun or a storie,
But alderbest he song an offertorie,
We expect he is reading and singing so well because he is earnest and sincere in his worship. We learn though that his motive is to impress people so they will buy his relics that are meant to provide them pardon for their sins. This is irony, and again, because the narrator's tone is so sympathetic, the irony is amusing rather than shocking and repulsive.
For wel he wiste, whan that song was songe,
He moste preche, and wel affile his tonge
To wynne silver, as he ful wel koude;
Therfore he song the murierly and loude.
In church, he was a noble cleric there;
He read well both the lesson and the story
But best of all he sung the offertory,
For he knew fine that once that song was sung,
He must preach well and keenly hone his tongue,
To win as much as he could from the crowd,