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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
The Princess Bride
The Princess Bride

Fezzik is supposed to be the third world

I had to do a character analysis of one of the characters from this movie for English 101, and being inspired by Everyone Is Jesus in Purgatory this is what I came up with:

Fezzik’s initial appearance in the movie is that as an oaf being manipulated by the little booger Vizzini clearly parallels the history of colonialism in the third world. For example, Vizzini keeps Fezzik in check by threatening to “return him to Greenland.” British, Dutch, French, and Spanish colonial overlords often justified their colonial conquests by saying that they were bringing civilization to them in the form of medicine, trains, and Christianity. It is obvious to see the similarities between Vizzini “rescuing” Fezzik from Greenland, and European powers “rescuing” the third world from primitiveness. Of course however, Vizzini does not actually care about Fezzik’s safety and just spends the better part of the beginning of the movie manipulating him to do his evil bidding, such as kidnapping Buttercup. And of course, most of the colonizers did not care about their colonies, rather they manipulated them for natural resources and cheap affordable labor. Vizzini’s wicked actions reach a climax when he forces Fezzik to defeat the man in black (Westley, Buttercup’s lover.) This leads to the next phase in the 20th century history of the third world: decolonization.

The defeat of Fezzik at the hands of Westley is both a low point and a high point for him, just as decolonization was for the third world. When Vizzini orders Fezzik to defeat Westley, he fails and is rendered unconscious, and Westley goes on to kill Vizzini. The high point of this is that he is no longer under control of the bloodthirsty and genocidal Vizzini, but the low point is that he was defeated and is unconscious. After World War 2, Britain, France, and the Dutch all agreed to give up their colonial possessions due to the fact that the war meant that they could no longer financially support maintaining them. While this may seem like a high point for the third world, it was also a low point. The rapid retreat of the Europeans meant that racial, religious, and economic tension reached its breaking point; and most of these regions became unstable and racked with civil strife. For example, India was split into India for Hindus and Pakistan for Muslims at a great cost of life that is still a problem even today. In Uganda, several evil warlords took control until they were overthrown by the bloody Hitler-esque Idi Amin who engaged in a terrifying revenge crusade of mass murder against certain ethnic groups. Even today, in places like Sudan and Darfur, the effects of decolonization can still be seen in the mass murder and ethnic cleansing. However, the biggest problem after decolonization, and for Fezzik after being defeated, is to figure out what to do now that they were on their own.

The answer for the third world was to become entangled in the Cold War, and for Fezzik was to become entangled in Westley’s quest. When the Cold War really brewed up, it was often third world countries like Ethipoia, Iran, and Afghanistan that served as the battleground between the United States of America and the Union of Soviet Socialist Republics, even though they really had nothing to do with either country: they were just being used as pawns to achieve each countries greater goal (communism vs. capitalism.) In the movie, after Fezzik is defeated by Westley, he could begin a fresh and live a new life, but rather, he returns to the delusional paranoid Inigo, and ends up getting entangled with his quest of revenge, and Westley’s quest to overthrow the royal family and bring political and economic instability to the country. However, Fezzik obviously has nothing to do with either quest, just like third world countries had nothing to do with George Washington or Vladimir Lenin. The USA and USSR used the third world for natural resources, military training, and basically to do the harm to each other that they couldn’t do directly. In the movie’s climax, Westley and Inigo force Fezzik to smash doors, scare enemies, find transportation, and even carry the lazy “paralyzed” Westley. The poor third world and Fezzik were simply not strong enough however, to over through their puppeteers and be truly independent.
  • This is just crazy enough to be true...

Vizzini is still alive
He's immune to iocane powder as well. "Never go in against a Sicilian when death is on the line". He's behind the rest of the movie because he planned for every event that happened. He was gloating because he knew that Westley was going to fall for his trap thus:
  • Vizzini realized right away that they were being followed by the Dread Pirate Roberts and realized that he had an opportunity. He had to know about Humperdinck's right-hand man Rugen being the six-fingered man, and no doubt Inigo had told him about his lifelong quest. He also knew that D.P. Roberts wanted to capture Buttercup (the actual reason why is unimportant). Therefore Vizzini decides to double-cross Humperdinck and get Westley or Inigo to go after him. In the end, Rugen is dead, Humperdinck has been humiliated and his Castle Guard has run away, leaving the door wide open for the thieves from the Thieves' Forest led by Vizzini to get in, kill the King, Queen and Humperdinck and take over Florin. All Hail King Vizzini the Bald!

Miracle Max's wife was the one who gave Buttercup the dream about marrying Humperdinck a week before the wedding.

The woman even went so far as to begin shouting at Buttercup in her own dream, for Heaven's sake. Being the wife of a guy like Miracle Max (and thus implied to have powers of her own), it's not inconceivable she could pull something like that off.

Note that this theory is for the film.
  • Valerie didn't shout at Buttercup in her own dream. The credits show Valerie and "The Ancient Booer" as two separate people/actors.
    • Don't you think if she can influence someone's dreams, she can make herself look like whatever or whoever she wants in them? And she also messed with the end credits.

Max sent that dream.

Westley is actually...
Count Rugen's nephew, abandoned at a young age by his parents because Count Rugen wanted no heirs (having learned that killing Inigo would grant him immortality ala The Seer from Kid Radd)

Westley is an Immortal.
That is how he got to be so good at fencing, wrestling, climbing and sailing. He had been alive for several centuries and was in fact the original Dread Pirate Roberts. The Count's Machine robbed him of his immortality though.
  • Or maybe it didn't. The Machine should have killed him, if not aged him. But (going by the film here) he is unaged, and only "mostly" dead...

The five greatest kisses in history are between...
  • What do you think? I'd set on my list: Cleopatra and Caesar; Romeo and Juliet; Tristan and Isolde; don't know about four and five, what do you think?
    • Will and Elizabeth, obviously.
    • Michael and Fredo. No one said they had to be romantic kisses.
      • Ditto for Judas and Jesus
      • Actually, the book says that the formula is something like affection x duration x purity x passion, so I'm trying to imagine a Jesus/Judas kiss that matches that...
      • Jesus Loves You And Everyone, so there's the affection... The Passion of the Christ is well known... Jesus=Purity... So it must have been a short kiss, or there's no way the one in the story could surpass them all.
      • Judas x Jesus was probably just a peck on the cheek or two, as per Mediterranean greeting custom.
    • Achilles and Patroclus. No-one said they had to be straight, either.
    • Desmond and Penny.
    • Robin and Starfire in Teen Titans: Trouble in Tokyo.
    • Mulder and Scully in "The Truth (II)".
    • Noah and Allie in The Notebook.
    • Jimi Hendrix and the sky.
    • Jimi Hendrix and this guy.
    • Cupid and Psyche.
    • Sleeping Beauty and the Prince
    • Aang and Katara's finale kiss.
    • Heracles & Omphale.
    • Me and Your Mom.
    • Kirk and Spock. (Oh c'mon, they've held hands countless times. That's Vulcan kissing right there.)
    • If that is the accepted formula, then it probably would rank in the number one spot. However, I think that Will and Elizabeth's kiss should be first, but there was a factor involved (I'm not sure what is should be called; Hilarity? Circumstances?) which isn't accounted for in the standard formula.
    • The inventor of the kiss and his or her love interest... Well, technically inventors, possibly.
      • The inventor of the kiss and his or her platonic but helpful next-door neighbor, or assistant (or assistant).
    • Buttercup with Wesley's stunt double.
    • Buttercup and Westley... when Westley left the farm.
  • Okay, it's supposed to be Wild, but considering it's supposed to be a reference in a book Grandpa's father read to him, perhaps we should limit our guesses to people who live a couple of generations or further back?
Sparks!
  • I believe several of the characters are actually sparks. Westley is due to his...inconceivable physical prowess and planning abilities (physical abilities seem to be a sparky trait) Count Rugen is thanks to the laws of nature warping machine though a weak one due to how long it took him to develop it. Miracle Max is because well...did you look at his name?

Buttercup is descended from Rohan.
No, really, Rohan. She's a wonderful horseback rider, and loves riding her horse more than any other activity. We know that Middle-Earth eventually becomes Europe, and The Princess Bride is set before Europe. More to the point, look at the words that all the Rohirrim use. Théoden means "king" in old English, and Meduseld means Mead-Hall. "Hello. I am King King. This is my mead-hall. I like to call it, Mead-Hall." The book states that Buttercup named her horse "Horse" (she was never long on imagination.) Could it be any more obvious?
  • You apparently misheard the above narration. The Princess Bride" is set "after Europe, and before America.'"
    • Ah. How very right you are. Well, she could still be a descendant...
    • No, it's after America, because that's where Westley tries to go to make his fortune, but it's before Europe because Scandinavia hasn't become attached to the rest of the continent yet.
    • I thought it was before Europe, after America, in between Africa and underneath Asia.

Rugen was poisoning the King on Humperdinck's orders.
Humperdinck: She's been like that ever since the fire swamp. It's my father's failing health that's upsetting her.
Count Rugen: ...Of course.
Narrator: The King died that very night, and before the dawn...
The old dude didn't appear to be in failing health. Old, maybe, but certainly not sickly.
  • The king "dying" was a dream sequence. The King lives through the whole movie and book.
    • Just because he didn't die before the villains were overthrown, doesn't mean he wasn't being poisoned. And that makes it more likely that Rugen poisoned him within the confines of the dream, if he survived in waking life (never saw him later in the movie, and it's been far too long since this troper reead the book).
    • Uh, yeah, he does show up later in the book. Right after the actual wedding, he walks Buttercup back to her room, and he's fine (if senile). Plus, in the book, Humperdinck didn't want to be king. All he wanted to do was hunt, go to war, and kill animals in his Zoo of Death. He saw his princely duties as a chore at best, and only sought out a bride at all because he had to. He wouldn't have wanted his father killed, because that would mean he would have more responsibilities to keep him from having his fun.
    • Point of order: the OP was speaking of the movie version. There's no indication that Movie!Humperdinck didn't want to be king. So it is possible he was having his father poisoned and intended Buttercup to be his queen as well as princess and wife. On the other hand, I can't see Rugen dealing in poison...unless it was because it was so slow-acting (perhaps even addling Lotharon's wits further?) that its usage was also a form of sadism...
    • He appears later in the film, too. After Buttercup's "wedding" to Humperdinck, she thanks the King for treating her well, gives him a kiss on the cheek and tells him that tonight she will kill herself. The King, so shocked and pleased by the kiss, completely misses the last part and walks away grinning, saying, "She kissed me!"

The Grandfather made up half the story on the spot.
The book he was reading really did play it as straight and as sappy as the title implied, and he knew it, so he spiced the story up with comedic twists in order to amuse his grandson.

Alternatively, The Grandfather made up half the story on the spot for another reason.
Not only was Morgenstern's original big on satire, but also of the Deconstruction of faerie tales— Westley actually does die, and Humperdinck does win. But after seeing how distraught The Kid was about the 'real' ending, he made up the rest of the story so The Kid would feel better.
  • This is canonically what happened in the original book (which says that Morgenstern's 'original' had a bad end, which his grandfather would change to a happy ending when retelling it.)

Or, quite possibly, The Grandfather made up half the story on the spot for a completely unrelated reason.
You see, the story he was going to read was Harry Potter and the Leopard Walk up to Dragon, which he realized on the way there was it isn't really a Potter book, but a farce. So he quickly swapped the cover with another book, and tried to pass it off as a romantic comedy, editing out every mention of the One Ring of Power. As follows.
  • Westley is Ron (note the similar spelling between Westley and Weasley)
  • Humperdinck is Gollum. Because he can be.
  • Buttercup is Hermione, because she messes with all the Shippers theories.
  • The ROUS is a hobgoblin.
  • All wizards in both the Potter parts and the LOTR parts are replaced by Tim the Enchanter, who was then replaced by Miracle Max for copyright reasons.
  • Obviously Fezzik is Hagrid.
After that, he actually makes up a better story than the one he was going to read. The twist at the end of the book version, where the kid is shocked to see the in-universe ending, is actually him being terrified at what Grandad bought him.
  • Except Harry Potter wasn't first published until 1997, ten years after the film came out. J.K. Rowling didn't even think of the character until 1990, according to The Other Wiki. So why would the Grandfather be about to read a parody of a franchise which didn't even exist yet?

The poison was in neither of the glasses
  • Roberts made up all that stuff about building up an immunity in order to impress Buttercup. So how did Vizzini die? Simple. You know how Roberts gave him the poison and told him to sniff it? Yeah. The whole "Battle of Wits" was just to distract Vizzini while the poison he had already sniffed was killing him.
    • Another possibility: There was a contact poison on the vial. Observe that Roberts did not remove his gloves to handle it, but Vizzini accepted it barehanded.
    • That is a very intriguing possibility...

Buttercup's "I do" was required
Women did not need to say "I Do" until the 1800s (I know it's not set in a particular time period, shush) because a noblewoman was forced into marriage, and this started a big war between nations that no one could stop, because divorce was not an option. So the people in power decided that, yes, noblewomen do have to say, "I do." This may or may not have spread to lower classes, but the choices were to call her common or note she hadn't said "I do," so...

Iocane powder is really, truly, odorless and tasteless.
(Yes, it also dissolves instantly in water.) Why could Humperdinck tell what it was anyway? Westley chose his poison well. It is the only thing on Earth that Humperdinck can't smell or taste.
  • Confirmed in the book. "I know of nothing else that kills so silently."

Iocane powder is odorless and tasteless because it anesthetises the olfactory receptors and taste buds before they can tell the brain something funny is going on.
Vizzini was so wrapped up in gloating that he didn't realize that the Iocane had numbed the bare surface of his tongue and inside of his nose and sinuses as the poison made its way to his heart. Him getting worked up while gloating only served to kill him more quickly.

In an alternate timeline, this movie was produced by Mel Brooks.
He plays Miracle Max.

Somehow, The grandfather IS Westley.
At a "movies under the stars" thing in her town, after the grandfather said the final line of the film ("As you wish"), a little boy seated by her screamed out "He was Westley! I KNEW he was Westley!" Of course this makes no sense in the context of the film, but it's a charming idea and could actually work if you look at it like this- the grandfather is making up parts of the story as he goes along and is basing the characters on people he knows as he retells it (like Adam Sandler in Bedtime Stories, for example). Westley is a Marty Stu version of grandpa, Buttercup is grandma (perhaps he had to leave her to fight in a war and was MIA), Humperdinck is some a-hole she almost married instead of him, Inigo and Fezzik are grandpa's army buddies.
  • Heck, considering the fact we don't know exactly when the story took place (because all of the weird "before Europe/after America" comments are only in the book), there's nothing saying the events of the movie couldn't have happened exactly as stated, with the Grandfather being old enough to have lived in Florin when young and been Westley. (If so that would suggest the Machine really didn't take away 50 years, or the pill restored them.) Or perhaps the Grandfather is a descendant of Westley and Buttercup and thus knows the family history, uses the catchphrase, and reads it to his grandson as the story has always been passed on through the family. Though your simplified modern version works too.

The Grandfather is really Lt. Columbo
We know Columbo is married, and the Grandfather has a coat and "did-I-forget-anything" pat that are nearly identical to Columbo's. Clearly the Princess Bride is a stealth crossover with a long-running crime drama.

The Ancient Booer IS Buttercup.
She knows everything Buttercup did, including things she thought in her own head. She knows Westley is her true love, and that he saved her in the Fire Swamp, though surely neither of those things would have been talked about by her or Humperdinck. She chastises her for abandoning Westley, for turning her back on true love, basically acting as her conscience and calling her all the terrible names Buttercup is secretly calling herself. And in the final moments when the Booer is shouting at her, and Buttercup sits up from her Catapult Nightmare, there's a startling similarity in the shapes of their faces and features when one replaces the other. So...the Booer is Buttercup's future self, having become old, bitter, and hateful thanks to living a life alone with Humperdinck, without her True Love. She doesn't know Humperdinck intends to kill her, so her own mind produces a future version of herself to warn her from this path before it is too late.
  • Er...it's a dream Buttercup is having. Technically, everyone in it is her—that is, a part of her subconscious. She needn't be dreaming anything as specific as "my older self who made the wrong choice travels back in time to warn me" for that to be true.

The Grandfather is William Goldman
And the kid is his grandson, William Arnold (from the book.) One of the first thing the Grandfather says is that his father used to read it to him when he was sick, which we know he did from the book, and he used to read it to the kid's father, (which he tried in the book, but his son never got into it.) And again, as we know (from I think the prologue to Buttercup's Baby) William Arnold fell in love with the book, just like his grandfather. So the movie is actually a dramatization of how William Goldman read the book for the first time to his grandson.

Humperdinck fired Max because of how good Max was at his job.
Consider: Humperdinck was planning to murder his bride and frame Guilder for it. But when Buttercup was found dead, would not everyone expect Humperdinck to immediately bring her to Miracle Max, in case Max could bring her back? And what if Max succeeded? That might ruin Humperdinck's whole scheme. So Humperdinck fired Max, claiming he was incompetent, to get him out of the way.

Inigo took some of the Miracle Pill.
During the duel he got stabbed in the stomach with a knife yet despite that he is still alive and managed to kill Rugen. This troper saw earlier that when he gave The Man In Black the Miracle pill, that he held it in his own mouth briefly before force feeding it to him. I at first thought he merely kissed it for luck, but now I think he took a bite out of it so he could have his own miracle.
  • Which also explains why it takes such a long time for Westley's body to wake up! He didn't get the full effect of the miracle pill!

Humperdinck is going to kill his stepmother.
As Humperdinck said:"I do not accept your resignation, you are doing a capable job, there is no plot, I shall slaughter the Queen myself this very evening, you shall run Guilder for me after the war, now get back on your feet." While he may have been refering to Princess Buttercup she is no longer there so he has no choice but to kill the actual Queen to use that to start a war with Guilder.
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