Who Won the Free Dinner in The Canterbury Tales?

Ranking The Canterbury Tales from Least to Most Readable

If you aren’t familiar with The Canterbury Tales, it’s about a group on a pilgrimage who tell tales to win a free dinner from the host of an inn. The person who tells the tale of “best sentence and most solas,” which means the most significant meaning and the most delight, ultimately wins the free dinner. 

Originally, Geoffrey Chaucer planned on writing around 120 tales, but only completed 22 tales and 2 fragments before he died. So we never figure out who won the free dinner. If you’re anything like me, that kind of ambiguous ending drives you crazy. So in lieu of Chaucer’s judgment, I’m ranking the tales that he was able to complete. I will try to follow the Host’s rules and judge for “best sentence and most solas,” although I doubt I will adopt the Host’s tastes (and I don’t think I want to). 

Side note: I’m not including The General Prologue in the rankings, but I definitely recommend reading it first if you haven’t already, since it provides the framework and introduces the characters. I’m also thinking of each respective prologue and tale as one when I’m ranking the tales.

I tried to avoid spoilers, but if there are any (I think there’s just one), I will warn you beforehand.

#24: The Parson’s Tale

To be completely honest, I’ve never read this tale all the way through. It is the last of The Canterbury Tales that Chaucer was able to write, and I’m sure Chaucer purposefully put it at the end to round out the previous tales. Where the others are at least slightly satirical and some even risqué, this one is more of a sermon. It’s not in the structure of a story; it’s an extremely long exploration of penitence and repentance. 

In the General Prologue, the Parson is portrayed as the best character out of all those on the pilgrimage, so it makes sense for the Parson to want “to enden in som virtuous sentence” (63). Perhaps Chaucer the poet is intimating that the tales were a symbol for life: full of sin — some virtue, but mostly sin. However, the end of the Tales symbolizes the end of life, when we all must repent, or else we go to Hell. Everyone in the company is so different: they belong to different classes, different backgrounds, different personalities. Chaucer might be using religion and sin as the great unifier. A lot of The Canterbury Tales satirizes so many types of people; Chaucer is bringing the satire home with a serious note.

Despite Chaucer’s reasons for including the Parson’s Tale, I found it rather boring, and not really worth reading. If you know the Bible or the Christian religion in general, you probably know the material of the tale. I said before that it reads like a sermon, but it’s actually more of a summary of Christian ideology. You might as well read the actual Bible or listen to an actual sermon; it’s probably easier to digest.

#23: The Squire’s Tale

Many believe that Chaucer intentionally made the Squire’s Tale kind of awful. It was the first boring tale of the Tales. The Squire had a tendency to use flowery language and expound unnecessarily. And then the Franklin interrupts the Squire as politely as possible to save the Squire from further embarrassment.

There is an indication that story might involve incest and in his introduction, the Man of Law mentions that the only stories Chaucer hasn’t told are the ones involving incest and other such unnatural abominations. Interrupting the Squire’s tale could be a clever way of Chaucer commenting on his own views on incest and satirizing his own refusal to speak on the subject. Having the Squire’s tale start out more boring (if that was indeed Chaucer’s intention) may emphasize that incest tales aren’t worth telling. 

If my interpretation is correct, it is interesting how Chaucer is willing to speak on subjects such as rape and adultery, but not incest.

#22: The Monk’s Tale

The Monk is rather offended when he tells his tale, because the Host just said that monks are such great copulators; therefore, wives want to have sex with them and try out their pregnating skills. So the monk goes into a really long list of men who were victims of Fortune, like Adam of the Bible and Julius Caesar. Unfortunately, the monk doesn’t really have anything new to say. 

#21: The Cook’s Tale

This tale is rather short and unmemorable. There isn’t anything inherently wrong with it, there just isn’t much there. It speaks of a cycle of thievery and debauchery.

#20 and 19: Sir Thopas and The Tale of Melibee

Both of these are the tales Chaucer the poet gives Chaucer the pilgrim (his fictional persona) to tell. The reason Chaucer the pilgrim gets two tales is because the Host interrupts the first and begs Chaucer to stop his rubbish speech, but gives him another chance. Sir Thopas is supposed to be the inferior tale, but I would rather read that than The Tale of Melibee anyday. Although it is about a wise woman who speaks some sense to the men, the tale is rather longwinded. 

#18: The Prioress’ Tale

This tale is obviously and unapologetically antisemitic, which is why it ranks so low. (Again, keep in mind the separation of the author and the narrator. Chaucer isn’t necessarily antisemitic just because this tale is.) Outside of that, it has a sweet tribute to Virgin Mary and a martyred child.

#17: The Physician’s Tale

The reason this ranks so low is the ending, which I can’t tell you because it is a spoiler. But it’s basically the epitome of toxic female oppression. It reinforces the idea that women are not worthy if they are “tainted,” even if they did nothing wrong.

#16: The Canon Yeoman’s Tale

This is one of the many instances of corrupt people in the religious order. The Canon basically uses the little-known science of alchemy to trick people and tries to teach the Yeoman (his servant/apprentice) the “trade.” If you decide to read this one, be warned; there are a lot of alchemy terms that bog down the tale.

#15: The Second Nun’s Tale

The beginning and the end of this tale isn’t too bad, but the middle is all fluff. It’s the story of Saint Cecilye and how she converted a bunch of people to Christianity despite incredible odds and persecution.

#14: The Nun’s Priest Tale

A dairywoman’s cock’s favorite wife emasculates him, and then the cock falls into the trap of the very threat the hen emasculated him for. It does have an interesting discussion of dreams, and another instance of a man claiming women are the root of every evil, but that’s about it.

#13: The Clerk’s Tale

This revolves around a husband that spends his entire life testing his wife, who happens to be THE most loyal and compliant wife in history. Even after this dude pretends to kill their children, she doesn’t change her attitude of love towards her husband. If Custaunce in the Man of Law’s Tale represents Christianity, then this tale’s heroine, Grisilde, is Job. And of course, the maniacal husband and his purest fool of a wife live happily ever after.

As much as the tale makes me roll my eyes, I was kind of impressed by the Clerk’s attitude towards his own tale. He says that men should not test their wives as this husband does, and says: “Though clerkes praise women but a [little] / Ther can no man [be as humble] / As women can, he can be half so trewe / As women can” (935-8). Ultimately, his message is not to emulate Grisilde as a humble, consenting wife, but be constant in adversity like Grisilde.

#12: The Reeve’s Tale

After the Miller tells a tale about a cuckolded reeve, the Reeve strikes back at him with a tale about a duped miller. The tale belongs to the fabliau genre (usually comic and obscene) like the Miller’s Tale, but is told out of revenge rather than a good-natured joke, so it is naturally less funny. 

The tale is also quite problematic. The women’s consent to men coming into their beds was questionable at best. But the tale seems to insinuate that both women enjoy the rape, the implications of which is a long conversation that takes us through a long history.

The reason it doesn’t rank even lower on the list is because it’s well told and I thought the context of the tale was interesting even if I was appalled at its subject matter.

#11: The Franklin’s Tale

This tale is about devotion, deception, mutual respect, and kept promises. It is actually a nice story, but it didn’t speak to me as much as the ones that rank higher.

#10: The Manciple’s Tale

This one’s kind of fun, because it gives people a reason not to tell their buds if their significant other is cheating on them. 

#9: The Shipman’s Tale

This tale is about a cuckolded husband (shocker) but is mostly about a very corrupt monk who manages to trick everyone in the tale. Chaucer liked doing this: revealing the Church’s corruption through satire. 

#8: The Pardoner’s Tale

For one, the Pardoner himself says he’s particularly suited to preach against greed, since he is guilty of this sin. The Pardoner does a lot of preaching at the beginning, but it’s kind of amusing, because it’s coming from such a corrupt individual. But the ending is morbidly funny. The tale reads like a classic guard-yourself-against-greed warning, but it’s told quite well. 

#7: The Man of Law’s Tale

This one is also kind of lengthy, but not at all boring. It’s about Custaunce: a beautiful woman so desired by a man that he converts to her religion. He is killed by his own mother because of his conversion and the mother sends Custaunce out to sea. She somehow survives and finds land, manages to convert more people to Christianity, and survives another treacherous mother-in-law. 

Custaunce is perhaps an allegory for Christianity. Whatever she is, she seems to be more of a symbol rather than a woman. 

#6: The Merchant’s Tale

This tale is a bit of a slow starter. I don’t think anyone would blame you if you wanted to skip the first half. It basically just says that an old knight (January) couldn’t take pleasure in an old wife so married a young one (May). Once married, all January wanted to do was jump her bones. 

But the second half of the tale is probably the most risqué of The Canterbury Tales. I won’t tell you how, because I don’t want to spoil anything. Anyway, the tale is supposed to prove a woman’s deceitful nature (almost in response to the Clerk’s tale that came before the Merchant and actually spoke well of women). 

#5: The Summoner’s Tale

The Friar’s entire tale is just a jab at summoners, and you can be sure the furious Summoner paid him back for that. It’s about a friar who tries to convince a patron to make him his one and only friar and angers the patron. The punchline ends in a colossal and hilarious fart joke.

My immature humor almost made me rank this better than the Friar’s tale, but the Friar’s entire tale is more interesting, whereas the fart joke is the Summoner’s tale’s saving grace.

#4: The Friar’s Tale (contains spoilers)

As I said above, the Friar’s tale is a jab at summoners. It’s about a corrupt summoner who meets a yeoman on the road who claims to dwell in Hell. The summoner asks the fiend to teach him devious tricks. The summoner goes to collect from an innocent old woman, who curses him to the devil. So the fiend literally takes the summoner to Hell. 

#3: The Knight’s Tale

The Knight’s Tale is fairly long, but it is actually quite entertaining to read. It may reveal Chaucer’s own biases and ideologies more than the other tales. It’s about two knights (who are also cousins) who fight over a beautiful woman, Emelye. It explores courtly love and how love is ultimately uncontrollable. Love is a higher power and can render men into fools: “Who shall yive a lovere any lawe?” (1164). Practicality and desire simply do not go together. This tale reminds me of the old saying: “All’s fair in love and war.” 

The only thing I don’t like about this tale is how the men speak for the women and don’t really allow them to make their own decisions. But, it is a product of the times. According to my professor, Chaucer was ahead of his time regarding women’s independence, so I suppose we have to remember to separate the author and narrator.

#2: The Miller’s Tale

The Miller is drunk when he tells this tale, and is only jesting. However, he starts a series of tales that “quit,” or “pay back” the previous tale. The Miller’s Tale is a response to the Knight’s Tale, or his way to “quit” the Knight. And then the Reeve in turn pays the Miller back, creating a pattern that continues throughout the Tales. 

I think the Miller’s Tale is the most humorous, as many others probably do. It’s about a cuckolded Reeve whose wife and lover plays a nasty trick on him for a night of ribaldry. If the contest was just about entertainment, The Miller’s Tale would win. However, I think it lacks enough “sentence.”

#1: The Wife of Bath’s Tale

I was honestly surprised when I ranked her tale number one, and I’m not sure if I like her prologue of her tale more, so this may be deviating from the Host’s rules, because I believe he only considered the tales themselves. However, considering the Wife’s character and the tale she tells, this one made me think the most.

The Wife of Bath is definitely one of the more fleshed out characters of The Canterbury Tales — a superbly complex character, and I’m not quite sure how I feel about her. I think she’s one of those characters that we are supposed to enjoy watching with our mouths open in shocked, incredulous “Os,” but hope she never enters our lives unless she is undoubtedly on our side, because she is a manipulator, and you’ll always wonder whether she might screw you over. 

But you can’t help but admire her, because she took all of the stereotypes about females that ran rampant in her age, and she used them to her advantage. Women are the downfall of men? Why, of course, she’ll make their lives chaos while she gets what she wants out of them. Women are supposed to be pure and chaste? She’s living proof of a successful woman who isn’t. In fact, she’s sexually free in a way that would shock the polite company of even today. Women are not supposed to talk or have an education? She’ll make you sit down and listen to her tale, and you’ll realize while you’re captivated that she’s educating you. 

She lives her life in direct opposition of what women of that age are supposed to be, but I have to wonder if she classifies as a feminist. Does she care about the fate of women, or does she just want to oppose standards so she can satisfy her own selfish desires? This girl was married at the age of twelve. I highly doubt that was her choice, and I’m sure she’s bitter about being forced to marry old men for money, so she turns that bitterness into belittling her husbands. And I know they are gross and pathetic for accepting a much younger girl in marriage, but seeing it in the context of the time period, I can’t help but feeling sorry for those husbands. 

Most importantly, I cannot imagine someone truly caring about women’s plight and then telling a tale where a rapist is pardoned without punishment and the victim not given a chance to speak against him. A woman does decide his punishment, but it’s the wrong woman. The Wife of Bath’s ideology seems so contradictory, but it all seems to boil down to the fact that she wants what she wants, to the point where she doesn’t care about the plights of others. Her whole life objective is to seize authority over men, and I’m not sure whether to admire her, pity her, or reprove her actions.

So, these are my rankings. I think if I adopted the persona and tastes of someone from that time period, I would have chosen The Man of Law’s Tale. But I’m just a girl living in the 21st century, so this is it. Let me know if you agree with them; I would love to know. And if you haven’t read The Canterbury Tales yet and you don’t want to read all of them, I hope this helps.