To identify celebrities who are similar to characters within Geoffrey Chaucer's The Canterbury Tales, one must be able to characterize them (the characters). Once characterized, one will be able to align each character with a celebrity.
The Knight is modest in both his speech and the way he presents himself (even with the amazing and important challenges he faces). A celebrity who can be matched with the Knight would be modest in character, refuses to flaunt his wealth, and does what others are not brave enough to do.
The Squire is similar to the Knight (since it is his son), yet the Squire likes to have a very good time. Therefore, a celebrity who could be compared to the Squire would be courteous, yet he would like to squander a little bit of his wealth to insure he has a good time.
The Prioress is a good woman who possesses both sympathy and good conscious. She believes in the concept of love conquering all else. A celebrity who can be identified for she similarity to the Prioress would be sympathetic and moral. She would believe in the power of love over all else.
The Friar knows those who work in the bar better than those who are in need of him (like the sick). He is a worldly man who is known as "the best beggar." A celebrity who could be compared to the Friar would be well traveled and tend to spend a little more time entertaining than working.
The Wife of Bath was married numerous times and was abused by her husband. She wants power over her man. A celebrity comparable to the Wife of Bath would be married numerous times (with most of the marriages being troubled).