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In The Story
Westley/The Dread Pirate Roberts
- Portrayed by: Cary Elwes
- The Ace: As Inigo puts it, stronger than Fezzik, more skilled than Inigo, and smarter than Vizzini.
- Acquired Poison Immunity: He has spent years "building up an immunity to iocaine powder."
- Back from the Dead: Thanks to the Miracle Pill.
- Bits of Me Keep Passing Out: Inverted and Played for Laughs as it takes a while for Miracle Max's cure to fully take effect on Westley, and Inigo and Fezzik have to carry him around while Storming the Castle as bits him are "waking up" one at a time.
- The Big Damn Kiss: "Since the invention of the kiss there have been five kisses that were rated the most passionate, the most pure. This one left them all behind. The End." Made ironic when the kid insists on skipping or editing all the kissy stuff at first but starts enjoying it by the end (film only).
- The Blade Always Lands Pointy End In: During his duel with Inigo Montoya, the Man in Black throws his sword. It spins end over end and impales itself in the ground point first.
- British Accents: Cary Elwes uses his native Ah Pea accent in the role.
- Cold-Blooded Torture: Damn you, Rugen.
- In the book, it goes a bit more in depth. Rugen tortures Westley through various methods while constructing The Machine, and Westley is shown to be immune to every single one of them by taking his mind away from the pain and imagining himself with Buttercup, though he fakes being in pain (which Count Rugen picks up on). The Machine, however, completely destroys this defense, and leaves him as little more than a quivering mess.
- Cool Mask: He wears a mask as the Man in Black.Fezzik: Why are you wearing a mask? Were you burned by acid or something like that?
Man in Black: No, it's just that they are terribly comfortable. I think everyone will be wearing them in the future.
- Dark Is Not Evil: As the Dread Pirate Roberts, Westley wears dark clothing and is a good guy.
- Deadpan Snarker: Before he reveals to Buttercup that he is indeed Westley, he occasionally snarks at her. Later he starts snarking at Humperdinck. Also, the whole conversation while he's climbing the Cliffs of Insanity.Inigo: Hello there! Slow going?
Westley: Look, I don't mean to be rude, but this is not as easy as it looks, so I'd appreciate it if you wouldn't distract me.
Inigo: Right, right. Sorry.
Westley: Thank you.
Inigo: I do not suppose you could-a speed things up?
Westley: Look, if you're in such a hurry, you could lower a rope or a tree branch or find something useful to do.
Inigo: I could do that. I have got some more rope up here. But I do not think you would accept my help, since I am only waiting around up here to kill you.
Westley: That does put a damper on our relationship.
Inigo: But... I promise I will not kill you until you reach the top.
Westley: That's very comforting. But I'm afraid you'll just have to wait.
Inigo: I hate waiting. Could I give you my word as a Spaniard?
Westley: No good. I've known too many Spaniards.
Inigo: Is there no way you trust me?
Westley: Nothing comes to mind.
- Death Is Cheap: He dies from the torture device. Miracle Max helps him shrug it off.
- The Dreaded: As the Dread Pirate Roberts, it's in the name.
- Farmboy: Starts out as one.
- Good Is Not Nice: Thanks to his perceived abandonment by Buttercup. Even after he finds out he was wrong, he's on the bitter and snarky side.
- Hair of Gold, Heart of Gold: He is almost made of gold, he's so good.
- I Am Not Left-Handed: Well, more like "I am not left-handed either." After Inigo starts fighting with his dominant hand, Westley does the same.
- Legacy Character: He's the Dread Pirate Roberts, the latest one specifically.
- Loving a Shadow: In the book it's hinted that he only really loves Buttercup for her beauty, and projects an imagined personality onto her since, as the narrator points out several times, he always gets annoyed and starts sniping at her whenever they actually talk in person. At the end the Lemony Narrator "guesses" that once Buttercup's looks start to go he'll eventually realize that her personality is such that he feels she isn't worth all the trouble he's gone through to get her.
- Master Swordsman: Can fight Montoya to a standstill.
- Names to Run Away from Really Fast: The Dread Pirate Roberts.
- Paper-Thin Disguise: Westley <-> Dread Pirate Roberts. It's amazing Buttercup takes so long to realize it. It also qualifies as Clark Kenting, although the book depicts him wearing a more complete disguise. Also, Buttercup had no reason to expect Westley to be alive, so she wasn't looking for him.
- Passing the Torch: In the film, Westley asks Inigo if he's ever considered piracy, implying that he will pass on the title of Dread Pirate Roberts to be with Buttercup.
- The Pirates Who Don't Do Anything: Mostly due to the reputation of the Dread Pirate Roberts, when merchants realize he is approaching, they give up immediately, sparing Westley from the fight. Although a popular fanon joke is that prior to reuniting with Buttercup, he spent several years pillaging and spreading terror.
- Pretty Boy: Oh yes. Cary Elwes is decidedly hot as Westley, especially compared to his later roles in Liar Liar and Twister, where he plays goofy/jerkass characters respectively.
- Resurrection Sickness: Westley is very weak after taking the Miracle Pill.
- Scheherezade Gambit: His relationship with the previous Dread Pirate Roberts.
- The Scream: He screams while in Count Rugen's Machine. Inigo and Fezzik find him because of it.
- Secret Test: The Man in Black doesn't reveal his true identity to Buttercup after he rescues her in hopes of finding out whether she still loves him.
- Something Only They Would Say: "As you wish," meaning "I love you." Former Trope Namer.
- Take No Prisoners: The Dread Pirate Roberts is known for leaving no survivors.
- To the Pain: Trope NamerWestley: To the pain means that the first thing you lose will be your feet below the ankles. Then your hands at the wrists, next your nose... The next thing you lose will be your left eye, followed by your right... Your ears you keep, and I'll tell you why: so that every shriek of every child at seeing your hideousness will be yours to cherish; every babe that weeps at your approach; every woman who cries out, 'Dear God! What is that thing?' will echo in your perfect ears. That is what 'to the pain' means; it means I leave you in anguish, wallowing in freakish misery, forever.
- Unable to Support a Wife: Why Westley went to seek his fortune.
- Wham Line: "As you wish" while falling down the hillside.
- You Fight Like a Cow: The famous Inigo/Westley duel, but with compliments and discussion of swordfighting tactics instead of insults. (In most DVD editions, that chapter is titled "The Chatty Duelists.")
- Portrayed by: Robin Wright
- The Big Damn Kiss: "Since the invention of the kiss there have been five kisses that were rated the most passionate, the most pure. This one left them all behind. The End." Made ironic when the kid insists on skipping or editing all the kissy stuff at first but starts enjoying it by the end.
- Damsel in Distress: She's especially useless in the fight with the ROUS. C'mon, swing that branch, don't just jab with it like a pool cue! Or pick up Westley's sword, or something.
- Dumb Blonde: Her hair is golden as the sun, but she's not exactly the brightest bulb in the box. Taken Up to Eleven in the book, where she borders on Too Dumb to Live.
- Everything's Better with Princesses: Buttercup gets promoted to princess, because she was born a commoner but Humperdinck wants to marry her. The book explains how she had to attend royalty school for three years, and was given the title of Princess of Hammersmith (which was part of the Florinese property but nobody ever paid attention to it) because the Prince couldn't marry a commoner.
- Green-Eyed Epiphany: In the book, the reason she realizes her love for Westley is because the Countess Rugen has the visible hots for him.
- Ice Queen: She flip-flops between this and Defrosting Ice Queen throughout the book: In the beginning she was an Ice Queen, then defrosts after she realizes her love for Westley. She freezes up again after Westley's reported demise, then defrosts after realizing that he's still alive.
- Informed Attractiveness: Regarding the movie: Princess Buttercup, while pretty, is far from the "most beautiful woman in the world". Then again, there are casting difficulties involved in finding a woman who could pass for the most beautiful woman in the world; not to mention the budget difficulties of paying her, and the possibility - indeed, the likelihood - that the most beautiful woman in the world can't act. Justified, though, as beauty is to the eye of the beholder and no matter who they picked she wouldn't appeal to everyone.
- Job Title: Her precise function in the story, at least as far as Humperdinck is concerned, is to be a princess and a bride. And a murder victim.
- Lady and Knight: After a fashion with Westley, even through she's not really a lady, and he's not really a knight
- Neutral Female: Buttercup is hilariously useless, at least until the end (of the book) when she manages to drive off the Brute squad by using her (false) authority as the Queen.
- Oblivious to Love: To Wesley, natch. This is made more obvious in the book, where he has to spell it out for her, whereas in the film she eventually realized it on her own. Also, in the book all the boys in the village fell in love with her as she neared that "most beautiful woman in the world" mark, so she was terribly annoyed when all those ridiculous girls in the village accused her of "stealing all the boys."
- Only One Name: Like almost every one else, with a notable exception.
- The Pig Pen: In the book, believe it or not. Before Westley left to seek his fortune across the sea, Buttercup almost never bathed or washed her hair, so an eternal layer of dirt, grime, and stink covered her. When she asks her parents how she can look her best for Westley when he returns, they instantly suggest a bath (something they'd been badgering her about for years). She's officially kicked of this habit when she goes into the three-year princess training from Humperdink.
- Pressure Point: Fezzik uses a Vulcan Nerve Pinch on Buttercup. In the book Vizzini does it.
- The Power of LoveButtercup: You can't hurt me. Westley and I are joined by the bonds of love. And you cannot track that, not with a thousand bloodhounds. And you cannot break it, not with a thousand swords. And when I say you are a coward, that is only because you are the slimiest weakling ever to crawl the earth.
- Played with in the wedding scene, where she fully expects that the Power of Love will cause Wesley to magically appear in the nick of time to stop her wedding—despite all the walls, gates, and guards—but he doesn't come. She has a Heroic B.S.O.D. over the fact that "he didn't come," and is almost Driven to Suicide until Wesley lets her know that since she didn't say "I do," it never happened.
- Quicksand Sucks: Ends up in one during her trek through the swamp. It doesn't last long.
- Rags to Royalty: From a farm girl to almost marrying the prince of the land.
- So Beautiful, It's a Curse:
- Her beauty is enough to get her promoted to future queen, except the Prince threatens to kill her if she refuses. And he's planning to kill her anyway. In fact, if she were slightly less beautiful, the whole conflict wouldn't have happened.
- Slightly averted in the book, where he originally had every intention of going through with the marriage, until he came up with the plot to frame Guilder. He specifically says to Count Rugen that he wants a wife who is so insanely beautiful that the whole world will be jealous, which is why Rugen shows him Buttercup in the first place.
- Threatening Shark: In the book, Buttercup tries to swim away from Vizzini, so he excites the sharks. In the movie, it was changed to the shrieking eels.
- The Ugly Guy's Hot Daughter: Both of Buttercup's parents (who are not in the movie) are hilariously ugly. Lampshaded when it's said they don't know how they managed to produce such a beautiful child.
- Unkept Beauty: Hinted at in the film's opening. In the book it's much more explicit, as before Westley left she had not yet gotten into the habit of things like bathing or combing her hair, so her beauty shined through despite (and later because of) her tangled hair and messy appearance.
- World's Most Beautiful Woman: The book even explains how she became the world's most beautiful woman, as well as what happened to the previous titleholders.
- Portrayed by: Mandy Patinkin
- The Alcoholic: After being bested by Westley, but he gets better. He was also one before Vizzini found him, having gotten depressed due to lack of worthy opponents and his inability to find Count Rugen.
- And Then What?: After killing Count Rugen at the end of the film, he remarks that, having been in pursuit of revenge for so long, he doesn't know what to do with his life now. Westley proposes that he take up piracy.
- Badass Spaniard: One of the most FAMOUS examples and badass in every way.
- Best Served Cold: His revenge against the six-fingered Count Rugen for killing his father.
- Catch Phrase:
- Cool Sword: A rapier. It was made for Count Rugen.
- Crippling Overspecialization: A lot of life skills like simple arithmetic are lost on Inigo, causing him to act rather brainless at times. The only things he really knows how to do are swordfight and hunt for revenge. Oh, and drink.
- Dashing Hispanic: So dashing, he's the trope picture.
- Determinator: During the duel with Count Rugen, he's stabbed multiple times, including in his arm muscles. After a Heroic Second Wind, not only does he not slow down, he fights even better than before. In the book he then collapsed during their escape when the adrenaline wore off.
- Dueling Scar: Inigo Montoya has two scars down his cheeks, which is understandable, given his career as a swordfighter. They are later revealed to be a humiliation inflicted upon him at the age of eleven after the first time he tried to avenge his father's murder by Count Rugen.
- Excuse Me, Coming Through!:Inigo: Excuse me...excuse me... Fezzik, please?
Fezzik: EVERYBODY MOVE!
Crowd: [clears a path]
Inigo: Thank you.
- Face Death with Dignity: When Westley defeats him, he initially thinks he is going to be killed and becomes very calm - his only request being a quick death. Luckily for him, Westley is even more good and honorable than he is and rebuffs the very idea of doing so.
- Good Scars, Evil Scars: Has classic good scars in the parallel slashes Rugen gave him to the face.
- Heel–Face Turn: Though he was never much of a heel to begin with. He turns from a Punch Clock Villain to a full-fledged hero after Vizzini is out of the picture.
- Heroic Second Wind: He's not going down that easily, Rugen.
- I Am Not Left-Handed: Trope Namer. Pulls this against The Man in Black. Backfires when it turns out the man in black isn't left-handed either.
- I Gave My Word: Played straight with Westley on the Cliffs of Insanity. He initially swears that he will get Westley up to the top alive on his honor as a Spaniard. Westley says that's no good ("I've known too many Spaniards.") He then swears on his father's soul, and Westley believes him.
- It's Personal: He's out to exact revenge on Rugen, the man who killed his father Domingo.
- Master Swordsman: Only Westley can equal him in swordsmanship.
- Minion with an F in Evil: He's ordered by Vizzini to kill the man in black. Inigo tries to do this by... throwing his opponent a rope to scale the cliff, let him catch his breath, and even have a friendly chat before they fight.
- Muscles Are Meaningless: Somehow this thin, lithe fencing master is strong enough to push 400+ pounds of Fezzik in a wheelbarrow while carrying Westley on his back.
- One-Man Army: Humperdinck's four elite guards didn't have a chance the second he appeared.
- Parental Abandonment: His father, Domingo Montoya, was a skilled swordmaker. One day Count Rugen comes to their nice, Arcadian village demanding a sword for a six-fingered man, offering to pay handsomely for it. Domingo accepts and for a year is either exceedingly happy or horribly depressed over his progress on the sword. When it is finally complete and Rugen comes to claim it, but attempting to pay only a fraction of the previously promised price. Domingo refuses to sell his finest work, crafted over the period of an entire year, for such a large discount and Rugen kills him for his defiance.
- Pay Evil unto Evil: He ends up killing Rugen, who is The Dragon to Humperdinck and the man responsible for Doflamingo's death.
- Physical Scars, Psychological Scars: Inigo Montoya has a scar on each cheek given to him by the man who killed his father which serves to strengthen his drive for revenge.
- Precision F-Strike: More of a B-strike, but he delivers one combined with a Pre-Mortem One-Liner when he kills Rugen.Inigo: I want my father back, you son of a bitch!
- Punch Clock Villain: He says it in the film — "I just work for Vizzini to pay the bills."
- Screw the Money, I Have Rules!: He's really quite an honorable man, though as he puts it, "there's not a lot of money in revenge."
- So What Do We Do Now?: Briefly at the end, he reflects that with Rugen dead, his revenge has been fulfilled and he doesn't really have anything to do with his life now. Westley suggests taking up piracy.
- The Slow Walk: During his final match with Rugen. Justified as he is seriously injured at the time.
- Spell My Name with an "S": "Inigo" is the English variant of the Spanish name "Íñigo," so some fans end up using the latter.
- Spexico: His movie incarnation seems to be going for this.
- Villainous Breakdown: A minor example - during his duel with Westley, after they both stop holding back Inigo noticeably starts losing control of the duel. The more Westley outperforms him the less reserved and more desperate Inigo becomes, until he's frantically slashing inanely in a mad bid to hit him. On the other hand, he calms down immediately once Westley disarms him.
- Wall Slump: During his final match with Rugen, after he's repeatedly injured.
- Worthy Opponent: Westley. The feeling ends up mutual.
- You Fight Like a Cow: The famous Inigo/Westley duel, but with compliments and discussion of swordfighting tactics instead of insults. (In most DVD editions, that chapter is titled "The Chatty Duelists.")
- You Keep Using That Word: Trope Namer when Vizzini says "Inconceivable!" when Westley evades Vizzini's attempt to make him fall from the Cliffs of Insanity.Vizzini: He didn't fall?! Inconceivable!Inigo: You keep using that word. I do not think it means what you think it means.
- Portrayed by: André the Giant
- Badass Baritone: Has a deep, booming voice, which he uses to great effect to imtimidate the soldiers in front of the castle.
- The Big Guy: He is a large man who uses his strength to kick ass when he needs to.Fezzik: It's not my fault I'm the biggest and the strongest. I don't even exercise.
- Black Cloak: Wears one as part of his "Dread Pirate Roberts" disguise
- Crippling Overspecialization: He's use to fighting multiple people at once, so he loses fast to a single, skilled fighter. He himself lampshades it.
- Dumb Muscle: Subverted. While not intelligent enough to be a Genius Bruiser, Fezzik is pretty clever when the situation calls for it.
- Elmuh Fudd Syndwome: He has a tendency to replace his rs with ws.
- Gentle Giant: To his friends, anyway. As strong as he is, he'd prefer not to fight at all.
- Giving Someone the Pointer Finger: While intimidating the soldiers.Fezzik: My men are here, I am here, but you [points] will not be here.
- Heel–Face Turn: Fezzik was never much of a heel, but after Westley spares him, Fezzik goes the extra mile to help Westley.
- Let's Fight Like Gentlemen: Forgoes Vizzini's underhanded ambush tactics for a straight up wrestling match with Westley. Westley's still grossly outmatched, but it's the thought that counts.
- Minion with an F in Evil: Like Inigo, he's only really working for Vizzini for money. He even decides to not go for the easy kill on Westley, since it's "not very sportsmanlike."
- Not Even Bothering with the Accent: He's supposed to be Turkish. André the Giant doesn't even pretend to speak in a Turkish accent in the movie and uses his natural French accent.
- Parental Abandonment: His backstory is never explained in the movie but his parents died of a desert plague while they were in Mongolia.
- Plot-Powered Stamina: His arms never get tired.
- Punch Clock Villain: Like Inigo, he works for Vizzini and that's the only reason he's a bad guy. The book explains that he takes the job because it means he won't be alone anymore.
- Rhymes on a Dime: Fezzik is very fond of doing this.Vizzini: No more rhymes, now, I mean it!
Fezzik: Does anybody want a peanut?
- Smarter Than You Look: Fezzik doesn't show it much, but he is able to annoy Vizzini with expert wordplay in his rhymes and is very resourceful. He provides the cloak needed to disguise himself as the Dread Pirate Roberts. Plus he explains Conservation of Ninjutsu to the Man in Black during their fight. He seems to be actually smarter than Inigo, whose obsession with revenge causes him to often make dumb decisions.
- Scarecrow Solution: "The Dread Pirate Roberts" rig that Fezzik wears. The Dread Pirate Roberts is a legendary figure who has been passed from person to person through the years. At the end, Fezzik dresses up and claims to be the "Dwead Piwate Woberts" to scare the castle guards.
- Portrayed by: Wallace Shawn
- Badass Boast: He's given a rather impressive one in the book in lieu of the Plato Is a Moron example in the movie.Westley: You are that smart?Vizzini: There are no words to contain all my wisdom. I am so cunning, crafty and clever, so filled with deceit, guile and chicanery, such a knave, so shrewd, cagey as well as calculating, as diabolical as I am vulpine, as tricky as I am untrustworthy...well, I told you there were not words invented yet to explain how great my brain is, but let me put it this way: the world is several million years old and several billion people have at one time or another trod upon it, but I, Vizzini the Sicilian, am, speaking with pure candor and modesty, the slickest, sleekest, sliest and wiliest fellow who has yet come down the pike.
- Bald of Evil: He has the least hair among him, Inigo and Fezzik and the most evil of all three.
- Big Bad Wannabe: He's set up as a decoy Big Bad after he kidnaps Buttercup, but the Man in Black kills him by tricking him into drinking poison about a minute after meeting him to make way for the true Big Bad and the man behind him, Prince Humperdinck.
- Book Dumb: In the book, he states that he has not had the schooling of some, though he is very clever and dangerous.
- Catch Phrase: Inconceivable!
- Character Exaggeration: In the book, he's an Insufferable Genius. The film, however, just makes him insufferable without really touching on the whole "genius" part.
- Disk One Final Boss: His plot to abduct and murder Buttercup make him the Big Bad (or at least The Heavy) of the earlier stages of the story. Once he's defeated, his employer and the true Big Bad, Prince Humperdinck, assumes the mantle proper.
- Evil Genius: So he keeps claiming, though his plans are never very complicated, and they all go wrong.
- I Don't Pay You to Think: Vizzini hired Fezzik for his strength, not his intelligence.Vizzini: You were not hired for your brains!
- I Know You Know I Know: While trying to figure out which goblet contains the poison. Also, the alternative name for this trope is "Wine in Front of me", named after this scene.Vizzini:...so I can clearly not choose the wine in front of me! But you would have counted on my thinking that, so I can clearly not choose the wine in front of you!...
- Insane Troll Logic: Uses this in an attempt to distract the Man In Black during their battle of wits. It probably would have worked too if the Man In Black hadn't poisoned both glasses.
- Jerkass: He doesn't think much of Inigo or Fezzik.
- Knife Nut: Wields a knife, which he uses to cut the rope the Man In Black is climbing after getting off it himself.
- Know-Nothing Know-It-All: Lampshaded by Inigo.Vizzini: HE DIDN'T FALL? INCONCEIVABLE!
Inigo: You keep using that word. I do not think it means what you think it means.
- Look Behind You: Pulls this on the Man in Black in order to switch the goblets.
- The Napoleon: He's noticeably shorter than both of his hired hitmen.
- No Indoor Voice: Just about every line out of his mouth is shouting as loudly as possible. Considering he's trying to be stealthy and sneak away with a kidnapped maiden, it's clear how much thought he's put into this.
- Out-Gambitted: Former Trope Namer. He thinks switching glasses when the Man in Black's back is turned somehow makes him smarter than the opposition. Not only does this end up killing him anyways, he never had a chance, since both glasses were poisoned.
- Plato Is a Moron:
- Poisoned Chalice Switcheroo: Not that it does him any good.
- Small Name, Big Ego: Let's face it, he's not nearly as smart as he thinks he is. He's given a bit more respect in the book, though, as Westley fully acknowledges how dangerous he is.
- Smug Snake: All he has is his brain and his loud mouth. He at least puts the latter to good use.
- Telepathy: In the book, Buttercup thinks he has this ability after he finishes her thoughts before she does. However, he admits this isn't true. He merely predicts the truth using logic and wisdom.
- Too Clever by Half: Ultimately his fatal flaw. He's hardly stupid, but his arrogance sometimes drives him to act like he is.
- Portrayed by: Chris Sarandon
- Adaptational Attractiveness: Played by the very handsome Chris Sarandon in the movie, though Westley still calls him ugly, both to his face and to Buttercup.
- Ambiguously Gay: Prince Humperdinck is the only character not swayed by Buttercup's beauty. He just views her as a political tool to convince his country to go over war for.
- And Now You Must Marry Me: The Scarpia Ultimatum version.
- Aristocrats Are Evil: He's not even trying to hide his schemes from anyone.
- Big Bad: He's planning on marrying Buttercup so he can murder her and go to war. He's also behind her kidnapping that lasts a big part of the story.
- The Chessmaster: What he seems to be going for, but he never quite hacks it. His plan is ingenious enough, but he loses control of it rather quickly.
- Dirty Coward: He's such a coward that Westley decides that simply letting him live the rest of his life as one is a far worse punishment than killing him.
- The Evil Prince: He's a textbook example, straight out of Machiavelli.
- Fat Bastard: Only in the novel, though he isn't fat so much as he is stocky. The first we see of him in the book he's wrestling an orangutan and breaking its neck.
- Faux Affably Evil: As polite as he is, it just makes him seem like more of a prick.
- Great White Hunter: More prevalent in the book than the movie, but even in the movie, Buttercup notes that "he can track a falcon on a cloudy day." He also deduces the nature and outcome of the duel between Westley and Inigo by examining their footprints.
- Jerkass: In the book, he's described that at his best, he's little worse than a man and that at his worst, he's little better than a beast.
- Karma Houdini: As the Grandfather points out halfway through the film, Humperdinck lives. Subverted, as he has to live with the realization that deep down, he is a Dirty Coward and will always be one. To Humperdinck, a man obsessed with hunting and war, this is a fate worse than death.
- Kingpin in His Gym: In the book, we first see him wrestling with an ape.
- The Man Behind the Man: He hired Vizzini to kidnap and kill Buttercup.
- Prince Charmless: He hasn't the slightest bit of tact or subtlety to him, even to the woman he wants.
- Properly Paranoid: "I believe everything to be a trap. It's the reason I'm still alive."
- Romantic False Lead: Everyone except Count Rugen genuinely believes that he's in love with his bride-to-be.
- Scarily Competent Tracker: He manages to deduce some wine had iocane powder in it, despite it being odorless and tasteless. How he found out is anyone's guess. In the book it's explained he deduced as such because it was odorless and tasteless.Humperdinck: I know of nothing else that kills so silently.
- Succession Crisis: In the book, the whole thing gets started when Prince Humperdinck learns that his father is dying and he has to marry to produce an heir. FALSE.
- Wicked Stepmother: Subverted. His stepmother is actually quite nice, it's just that he grew up reading fairytales with wicked stepmothers and as such refers to her as "Evil Stepmother" ("E.S" for short), a term of endearment between them.
- Portrayed by: Christopher Guest
- Aristocrats Are Evil: He's an aristocrat and a bad guy.
- Beard of Evil: In contrast to the clean-shaven Humperdinck, he has a chin strap and a mustache.
- Character Death: He gets stabbed to death by Inigo towards the end of the story.
- Combat Pragmatist: He starts to assume a dueling pose when Inigo confronts him—then he runs away and ambushes him with a knife-throw once Inigo finds him. (It doesn't do him any good, in the end.)
- Creepy Monotone: His default way of speaking. Except in his duel with Inigo, especially once he starts losing.
- Deadpan Snarker: Towards the completely oblivious Humperdinck.
- Dirty Coward: When Inigo finally confronts him, he at first raises his sword to fight... then turns and runs away. When Inigo catches up, he ambushes him with a throwing knife. This is more justified in the book; the four swordsmen Inigo cut through in seconds are explained to all be master swordsmen themselves there (while in the movie they seem to just be mooks) so he knows a fair fight would effectively be suicide.
- The Dragon: He serves as this to Humperdinck.
- Even Evil Has Standards: He is a sadist that actually likes to document the reactions his victims have when they are being tortured by The Machine (this is for posterity), but he was horrified when Humperdinck turned The Machine up to 50 (when even Rugen said he would turn it to 5 at max) when it was Westley's turn. This is then subverted, however, as he quickly calms down and seems to serenely analyze Westley's reaction.
- Famous Last Words: He says "Anything you want!" before he gets stabbed to death by Inigo.
- Faux Affably Evil: His politeness is to mask his evil and vicious personality.
- Good Scars, Evil Scars: He has evil scars. Inigo eventually repays him for the good scars, too.
- Mad Scientist: He has a torture device set up, purely "for science."
- Never Say That Again: To Inigo after the latter repeats his Catch Phrase one too many times.
- Not So Stoic: The first time he raises his voice is when Humperdinck slams the torture suction device to its highest setting.Rugen:"NOT TO FIFTY!!"
- Psycho for Hire: Works part-time as Humperdinck's Exalted Torturer, a job he takes to with a level of satisfaction that can only be called psychotic.
- Red Right Hand: He has six fingers on one of his hands.
- The Sociopath: He has zero empathy for anyone, and expresses nothing but detached, professional interest while torturing people.
- Soft-Spoken Sadist: His manner vaguely resembles Hannibal Lector: he's very polite and never raises his voice, but he's a dangerously insane man who tortures people as a hobby.
- Torture Technician: He's something of a self-taught expert on the subject, inventing several torture devices and even writing a book on the subject.
- Villainous Breakdown: As Inigo refuses to die, and slowly gains the upper hand on Rugen in their duel, Rugen first becomes shaken, then demands that Inigo "Stop saying that!"
- Villainous Friendship: Type I with Prince Humperdinck.
Max and Valerie
Miracle Max and his wife Valerie
- Portrayed by: Billy Crystal (Max) and Carol Kane (Valerie)
- Alchemy Is Magic: It's never outright called "alchemy", but he does practice some sort of strange medieval chemistry that works a lot like magic. He's even called a magician.
- Ambiguously Jewish: Described by Billy Crystal (Max) as a pair of "Jewish trolls". Lampshaded in the novel.
- Berserk Button: Mentioning Prince Humperdinck's name will drive Max up the wall. Not that his wife cares.
- Happily Married: Not so obvious in the movie, but the book implies as much—for example, explaining that when Max calls Valerie "witch" it's in fact a term of endearment and part of their whole act.Valerie: I'm not a witch! I'm your wife!
- Henpecked Husband: Max.Valerie: LIAR! LIAR! LIIAAAAR!
- Like an Old Married Couple: Well.... They are an old married couple but even still, all their dialog to each other is in this vein.
- Portrayed by: Mel Smith
- Even Evil Has Standards: When The Machine is turned up to 50, his normally calm expression becomes one of horror.
- Evil Albino: He's an albino and works for Count Rugen.
- Evil Sounds Raspy: Parodied. He says his first line with an extreme rasp... then he clears his throat and speaks with a clear voice and a slight cockney accent for the rest of the film.
- Punch Clock Villain: He seems to enjoy (or at least accept) his job in the film a little more, though. In the book he's very timid and feels deeply sorry for Westley, offering to poison him to put him out of his misery.
- The Stoic: He barely says anything in the book at first, responding to most of Westley's questions with a shrug.
- Ultimate Job Security: When he offers poison to Westley to spare him from the pain of the machine in the book, he points out that only he is capable of tending to the animals in the Zoo of Death, and that no harm would come to him for his transgression.
- What Happened to the Mouse?: He's not seen after Fezzik knocks him out.
The Impressive Clergyman
- Portrayed by: Peter Cook
- Portrayed by: Malcolm Storry
- Badass Mustache: It connects with his sideburns.
- Dirty Coward: Gives up the keys when Inigo tells Fezzik to tear his arms off.
- Mook Lieutenant: Humperdinck's head of security and doesn't get much characterization than that.
- Nerves of Steel: He's the only one who stands his ground when Westeley, Inigo and Fezzik arrive (Fezzik disguised as the Dread Pirate Roberts). Subverted when actually threatened and gives up the keys.
- Puppet King: In the book, Humperdinck intends to make him ruler of Guilder after he conquers it, as he can't be in two different places at once, and he knows that Rugen wouldn't take the job, being obsessed as he was with the Machine.
- Resignations Not Accepted: In the book, after Humperdinck warns him of a (nonexistent) plot by Guilder to murder Buttercup, he hands in his resignation after failing to find a shred of evidence. Because Humperdinck still needs Yellin (as shown above in the Puppet King example), he does not accept his resignation and admits the whole thing is just an excuse to conquer Guilder.
Outside The Story
- Portrayed by: Fred Savage
- He's Just Hiding: Invoked.The Boy: Wait, what did Fezzik mean, 'He's dead?' I mean he didn't mean dead. Westley's only faking, right?
- Ill Boy: His grandfather comes to read him the story because he's been extremely sick. Not at death's door or anything, but still very sick.
- No Name Given: Though if the book's anything to go by, his name is William Goldman, the book's original author.
- Suspiciously Specific Denial: After his grandfather tells him that Buttercup doesn't get eaten by eels, he vehemently denies he was nervous about it, instead stating he was 'concerned'.
- Portrayed by: Peter Falk