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  • Adaptation Displacement: Many who can quote the movie from end-to-end don't even realize there is a book or that most of the famous quotes come directly from it. In the introduction to more recent printings of the book, William Goldman says flat-out that if you are picking it up for the first time, it's probably because you've seen the film.
  • Aluminum Christmas Trees:
    • In the intro story, Goldman complains that he had to argue with his editors about Max and Valerie being "too Jewish" for a medieval fantasy story — as though crotchety Jews were invented in the Catskills in 1952.note  He also relates a similar battle he went through with the "bifocals" line in Butch Cassidy and the Sundance Kid, fighting a studio executive who didn't know and didn't care that Ben Franklin invented bifocals nearly a century before the movie's period.
    • All four of the fencing masters mentioned by Inigo and The Man in Black are real historic figures. Rocco Bonetti is credited with bringing the Italian style of fencing to the British Isles and was the target of a hilariously one-sided hatred from British-born fencing master George Silver, Gerald Thibault D'Anvers was a famous fencer, mathematician, and alchemist, who attempted to create his "new" fencing based on geometric principles, Ridolfo Capo Ferro was another fencer, who famously advocated for being able to outrange one's opponent as the most important principle of fencing, and therefore was a warm proponent of excessively deep lunges and very long swords, and Camillo Agrippa was another proponent of geometric fencing and is also credited with creating "modern", thrust-centric fencing.
  • Ass Pull: The holocaust cloak, which is Played for Laughs. It strains the limits of credulity as to why Miracle Max (played by 5'7", 130 lb. Billy Crystal) would have possession of a cloak big enough to fit Fezzik (played by 7'1", 500 lb. André the Giant). Part of the reason it works is that the movie plays the absurdity for comedy. (The book mentions it briefly beforehand, Goldman claiming that Fezzik had needed one to fulfill a task in the - nonexistent - longer version of the chapter of "S. Morgenstern's" work.)
  • Audience-Alienating Premise: The movie's title counts for a male audience. The fact is that's a very accessible and funny adventure film that actually isn't that much focused on romance or targeted towards women isn't enough for certain people to overcome its Romance Novel-sounding title (though the movie's Cult Classic fame helps with this). The movie itself somewhat acknowledges this with the grandson's initial reluctance to hear a "kissing story", only to become enraptured with the rest of it as it goes on.
  • Award Snub: Despite having some of the most quotable lines in movie history, William Goldman's script didn't get an Oscar nomination.
  • Awesome Music:
    • The ending song performed by Willy DeVille.
    • Also the soundtrack, courtesy of Mark Knopfler. In the last sword fight, the timing of the music is perfect with the choreography, and the chords embody the dramatic tension and climax of the scene. This happens throughout the movie, but here it is most noticeable.
  • Broken Base: The score by Mark Knopfler, and specifically the decision to use synthesizers rather than a traditional orchestra. The music has received praise from some critics and fans, while others find it gives a dated 1980s feel to a movie that is otherwise timeless.
  • Captain Obvious Reveal: If you hadn't at least identified the actor playing the Dread Pirate Roberts as Cary Elwes, you certainly would after Buttercup comments on how Westley had "eyes like the sea after a storm," and the camera zooms on "Roberts" sea-blue eyes.
  • Complete Monster (novel only):
    • Prince Humperdinck is a man who loves nothing so much as to kill other things, having a menagerie of animals to hunt and kill at leisure. Applying this philosophy to the real world, Humperdinck plans to start a bloody war so his nation of Florin can conquer Gildor. Forcing the lovely Buttercup into marriage, Humperdinck tries to have her murdered and frame Gildor to give pretense for invasion, having her rescuer and true love Westley subjected to his right-hand-man Rugen's wicked Machine for torture, something he enjoys subjecting their victims to. Deciding upon murdering Buttercup with his bare hands, Humperdinck turns the Machine to its highest setting to give Westley the most agonizing end imaginable.
    • Count Tyrone Rugen, the "six-fingered man" Inigo Montoya has dedicated the past twenty years of his life to hunting, is the Prince's "twin in misery". A cold-hearted Torture Technician who seeks immortality through the science of human suffering, Rugen once offered a noble swordsmith named Domingo to slave for a year on a perfect sword, then offered only a tenth of his original price upon seeing the result. Rugen heartlessly murdered Domingo when he was refused and spared his son Inigo only a whim, leaving the boy with two scars upon his cheek to forever mark the moment. Rugen now writes what he hopes to be the "definitive work" on torture, testing his skills upon the captured Westley for weeks on end. Rugen's crown achievement is a ghastly device he simply calls "the Machine", meant to precisely drain years of life from its victims, that he first demonstrates on a dog before subjecting Westley to it, leaving him broken and sobbing.
  • Cult Classic: The film was unsuccessful at the box office, earning $30.8 million on a $16 million budget, but was so Vindicated by Cable that it's rather a disservice to say that it's only become a cult classic.
  • Ensemble Dark Horse:
  • Fountain of Memes:
  • Girl-Show Ghetto: This was part of the reason why the movie didn't do well on its first release. The marketing department at 20th Century Fox had no idea how to promote an absurdist swashbuckling adventure with a "girly" title and romantic arc and simply gave up and didn't release any promotional materials. Later, to compensate for the feminine-sounding title, some DVDs have a cover that puts the Dread Pirate Roberts in the front and center and emphasizes action in the synopsis, basically the exact same way the Grandfather talks it up to his grandson. On the other hand, some DVDs have Buttercup with a crown on the cover, with a very pink box, avoiding this.
  • Harsher in Hindsight: In his introduction to the 30th Anniversary Edition to the novel, William Goldman assures the reader that the sequel, Buttercup's Baby, will be in the reader's hands "in time for the 50th Anniversary Edition". While this was probably meant to just be a joke on how long it was taking, in real life Goldman died five years before the book's 50th Anniversary, with no sequel ever appearing.
  • Hilarious in Hindsight:
    • In the 1973 book, gamers will appreciate Goldman deciding to skip over the long and repetitive Fetch Quest Inigo and Fezzik undertake late in the book to procure the ingredients for Max's miracle pill. In fact, this is just one of many things that was abridged that sounds an awful lot like Fake Longevity in an RPG game specifically, as opposed to just general story-telling Padding.
    • The priest mentioning "a dream within a dream" becomes this with the release of Inception 23 years later, which used the phrase as a key part of the plot.
    • Fezzik's discussion of "fighting half a dozen people" seems prescient when you consider the 1989 Royal Rumble two years later, in which Andre The Giant takes out the first few fighters.
    • Cary Elwes can't stay away from torture and chains, can he?
    • At the end of the original introduction to his book, dated December 1972, William Goldman laments that high adventure (one of the selling points of the book) seems to be in short supply at the time; "Nobody takes out a sword nowadays and cries, 'Hello. My name is Inigo Montoya. You killed my father. Prepare to die!" Fast forward fifteen years or so, the movie comes out, and that very line has become one of the most quotable movie lines of all time, usually said while playacting a swordfight. The 30th Edition has a preface in which Goldman "traveled" to Florin and said kids were all imitating Inigo's catch phrase.
    • The "Ancient Booer" is appropriately named given that her actress Margery Mason lived to be 100.
    • During the fight between the Masked Man and Fezzik, Fezzik asks why the former is wearing a mask. Wesley quips that "they're terribly comfortable. I think everyone will be wearing them in the future." It seems oddly prophetic after everybody across the planet had to wear face masks due to the COVID-19 Pandemic. Cary Elwes even quoted the line on his Twitter.
    • Count Rugen's fingers go up to eleven.
  • Ho Yay: Humperdinck and Count Rugen anyone? And Inigo and Fezzik.
    • And Domingo and Yeste in the novel.
  • Informed Wrongness: Buttercup getting engaged to Humperdinck, even though a) it was three years after she believed Westley was dead (five in the film), b) Westley didn't bother to let her know he was alive or give her a reason to wait for him, c) her fiance was the crown prince of Florin and could have her imprisoned or executed for saying no (which he does threaten to do in the book).
  • It Was His Sled:
    • The Man in Black is Westley, and he has developed an immunity to iocane powder. Even if you don't know going in, Cary Elwes' now quite noticeable voice will probably tip you off. To his credit, Elwes at least tries to help the deception along by speaking softly and slowly early on, and in a much louder, faster, and more confident voice once he shows up as "Roberts".
    • Prince Humperdinck is the true Big Bad of the story. He doesn't love Buttercup and wants to kill her in order to justify a war against the neighbouring country. This fact is so much common knowledge that it's easy to forget that, in the movie proper, it's a twist that's only revealed after the death of Vizzini.
  • Just Here for Godzilla: Oh yes, it's that movie with Inigo Montoya! Wait, what do you mean he's isn't the main character?!
  • Memetic Mutation: Enough to warrant its own subpage.
  • Mexicans Love Speedy Gonzales: Australian fans are in fact very pleased by the line "...and Australia, as everybody knows, is populated entirely by criminals", and cinema screenings are often interupted by loud cheering after this line.
  • Misaimed Fandom:
    • Many viewers take the "True Love" aspect of Westley's and Buttercup's relationship seriously, not seeming to realize it's a parody of classic "World's Most Beautiful Woman + Swashbuckler hero" romances, given how appearance-based their love is note , and how little they have in common or get along when they aren't pining over each other from a distance.
    • A number of real-live couples model their wedding after Buttercup and Humperdinck's royal wedding with the priest with the speech impediment, even though, you know... she's been coerced to marry the Big Bad, who intends to strangle her right after the ceremony.
  • Moral Event Horizon:
    • Vizzini crosses it by mentioning the little detail where the Sicilian Crowd kills Buttercup, and later cements it by holding her at knifepoint when the Man in Black, having beaten both Inigo and Fezzik in succession, gets too close before their battle of wits, just so that his death by iocane—while he's still laughing in perceived triumph, no less!—can be considered all the more satisfying. Indeed, after everything it's not much of a surprise that he's the only one in the Sicilian Crowd to cark it in his showdown with the Man in Black.
    • Prince Humperdinck crosses when he cranks the Life Drain machine up to 50 to torture his romantic rival Westley to death. Even Count Rugen, who invented the machine in the first place, is horrified by the act.
      Humperdinck: You truly love each other, and so you might have been truly happy. Not one couple in a century has that chance, no matter what the storybooks say... And so I think no man in a century will suffer as greatly as you will.
  • Narm:
    • Fezzik's Mook Horror Show while wearing the holocaust cloak is intended to be played seriously while contrasted against the comical scene with the Impressive Clergyman... but both sides of the scene come across as somewhat comical thanks to the fact that André the Giant actually has the exact same speech impediment that the clergyman does, and has to call himself "the Dwead Piwate Woberts". This, along with his cloaked form obviously being an immobile dummy wheeled forward instead of a real actor in a flame suit.
    • Humperdinck responds to the first part of Buttercup's "Reason You Suck" Speech with the very cold, quiet, and well-delivered, "I would not say such things if I were you." After she follows up with an even more nasty and contemptuous speech, he repeats his words in a hammy, growling rage, and... proceeds to grab her arm, take her down a hall, and lock her in her room before going to kill Westley. It works for a villain as wimpy as he is, but for those who expected him to do something far worse to her (forgetting he had to wait till no one would blame him for her death, and intended to do it after they were married), it rather falls flat.
    • The R.O.U.S. can veer into this territory for some people because the effect wasn't particularly good for its time, and has definitely not aged well. In various shots it's either a little person in a mechanical costume, or just Cary Elwes wrestling a dummy.
  • Narm Charm:
    • Inigo's spent his whole life focused on his revenge on Rugen, to the point he clearly didn't know what to say beyond his Pre-Asskicking One-Liner. Patinkin's performance turns the ridiculous repetition into one of the high points of the film.
  • Nightmare Fuel:
    • The Pain Machine. We're given an idea of just how horrific it is when Westley is only briefly tortured on its lowest setting, and rather than making a defiant quip to Count Rugen afterward like a first-time viewer might expect, Westley immediately bursts into Broken Tears.
    • The old lady. Boooo! And if you can believe it, that was the tamest of Buttercup's nightmares in the book!note 
    • The Shrieking Eels from the film. They were sharks only mentioned in passing in the book, but in the film we get to see and hear them. To make matters worse, they're heard instead of seen. According to Vizzini, their shrieks "always grow louder when they're about to feed on human flesh".
    • The Fire Swamp, which is basically a miniature Death World, complete with telltale jets of fire bursting from the ground, quicksand that can swallow a person in seconds, and the R.O.U.S., that look and act like they belong in a much darker setting than the one given.
    • After Christopher Guest has become so popular for his litany of lovably eccentric characters, it can be quite startling to see him as a Softspoken Sadist played totally straight.
    • Even if it's totally deserved, the description of "To the Pain" leaves a heavy amount of Body Horror to the imagination.
    • The very concept of Iocaine Powder. It has no taste or scent making it completely undetectable, as well as killing it's victims almost instantly with no hint of even being poisoned (Vizzini dies mid-laugh with absolutely no clue that he was poisoned).
  • One-Scene Wonder:
    • Billy Crystal and Carol Kane in the Miracle Max scene. Rob Reiner had to recuse himself from personally filming the scene as he could never keep from laughing, and Mandy Patinkin hurt a rib trying to hold in his laughter during this scene. Cary Elwes had to be replaced by a dummy whenever they could get away with it, to prevent the dead body starting to laugh.
    • Peter Cook's impressive clergyman.
    • Mel Smith's Albino.
    • Margery Mason's Ancient Booer.
  • Older Than They Think:
    • Parodied in the book, with an explanation that a scene with Fezzik and Inigo going on minor quests to save Westley was 'cut' because it seemed like a ripoff of The Wonderful Wizard of Oz, even though the 'original version' came out first.
    • Vizzini saying "All aboard!". The book notes that this was before trains, but the saying actually comes from carpenters loading lumber, and this was well after carpenters.
  • Playing Against Type: Christopher Guest is best known for appearing in his series of mockumentaries and other projects as wacky, weird, or at least subtly funny characters. Here, he plays a straight-up villain with only a few extremely deadpan quips.
  • Retroactive Recognition:
    • Fans of Columbo and The Wonder Years should get a kick out of seeing Savage & Falk play off one another. Who knew the Detective had a Grandson?
    • Pixar fans ought to find it more than a little amusing that Rex and Mike Wazowski star in the same movie (though they never share any scenes together).
  • Signature Line: "Hello, My Name Is Inigo Montoya. You Killed My Father. Prepare to Die."
  • Signature Scene: The Battle of Wits between Vizzini and the Man in Black/Westley. The duel between the Man in Black/Westley and Inigo is a close second.
  • Special Effect Failure:
    • When the heroes leave on the four white horses, it is quite clear that Fezzik has a body double. Necessary, though, in that there isn't likely a horse in the world that could carry André the Giant's mass.
    • The dummy in the holocaust cloak in the far shots of the "Dread Pirate Roberts" is particularly bad. Especially since half the shots show the cloak's face engulfed in flame, but closeups show just some small fires, comfortably far from Fezzik's face.
    • The Rodents of Unusual Size are clearly guys in suits.
    • When the Machine is set to one, the water gate is clearly not holding back any water, since there is a noticeable gap of air between the stream and it. This would mean that when it's set to the maximum of fifty, the stream of water wouldn't be any higher.
  • Strangled by the Red String: Westley and Buttercup are basically this being done deliberately; their relationship development is completely skimmed over, they don't seem to get along much in the small number of scenes where they are together, and they don't seem to have any reason to be together other than that they both think they're beautiful. Fortunately, what they lack in development, they make up for in passion. (It's addressed in Buttercup's Baby.)
  • Visual Effects of Awesome: A highly advanced prosthetic finger was created that could move sympathetically with Christopher Guest's real ones. The result is so convincing that many at the time were convinced they actually did find a six-fingered person for the closeup shots of his hand.
  • Vindicated by History: The Princess Bride was a mild success in theaters, but strong word of mouth caused it to be very popular once it was released on home video. Its popularity has grown over the decades as new generations of young people have been exposed to it. It's now considered one of the most beloved and timeless films from the 1980s.
  • The Woobie:
    • Fezzik. Not so much in the movie, but after learning that in the book his parents forced him into wrestling at the age of nine and threatened to leave him forever if he wouldn't fight, you start to feel sorry for him.
    • Similarly, Inigo. He grew up dirt-poor and only had his father. Then, a nobleman kills his father for taking offense when the nobleman refuses to pay more than a tenth of the agreed-upon price for the sword he commissioned. Not only that but in the book, plenty of villagers knew the nobleman murdered Domingo Montoya. They all just let him leave though because there was no way they could convict him of his crime and focused on protecting the wounded Inigo.

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