!In The Story

!!Westley/[[spoiler: The Dread Pirate Roberts]]
!!! Cary Elwes

* AcquiredPoisonImmunity: [[spoiler:To iocaine powder.]]
* BackFromTheDead: [[spoiler:Thanks to the Miracle Pill.]]
* BitsOfMeKeepPassingOut: Inverted and PlayedForLaughs 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 StormingTheCastle as bits him are "waking up" one at a time.
* TheBigDamnKiss: "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).
* TheBladeAlwaysLandsPointyEndIn: 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.
* BritishAccents: Cary Elwes uses his native AhPea accent in the role.
* ColdBloodedTorture: [[spoiler:Damn you, Rugen.]]
* CoolMask: 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.
* DeadpanSnarker: 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.\\
''*{{beat}}*''\\
'''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:''' [[{{Understatement}} 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.
* DeathIsCheap
* {{Farmboy}}: Starts out as one.
* GenreSavvy
* GuileHero
* GoodIsNotNice: Thanks to his perceived abandonment by Buttercup. Even after he finds out he was wrong, he's on the bitter and snarky side.
* HairOfGoldHeartOfGold: He is almost made of gold, he's so good.
* TheHero
* IAmNotLeftHanded [[spoiler:either.]]
* LadyAndKnight: Or Lady and Pirate, whatever.
* LivingLegend
* MasterSwordsman: Can fight Montoya to a standstill.
* NamesToRunAwayFromReallyFast: [[spoiler:[[TheDreaded The Dread Pirate Roberts]].]]
* OnlyMostlyDead: The TropeNamer!
* PaperThinDisguise: Westley <-> Dread Pirate Roberts. It's amazing Buttercup takes so long to realize it. It also qualifies as ClarkKenting, 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.
* PassingTheTorch: [[spoiler: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.]]
* ThePiratesWhoDontDoAnything: 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 raping and pillaging and spreading terror.
* PrettyBoy: 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.
* PunctuatedForEmphasis: Drop. Your. Sword.
* ResurrectionSickness: [[spoiler:Westley is very weak after taking the Miracle Pill.]]
* ScheherezadeGambit: His relationship [[spoiler: with the previous Dread Pirate Roberts.]]
* TheScream: [[spoiler: While in Count Rugen's death machine. Inigo and Fezzik find him because of it.]]
* SecretTest: 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.
* SomethingOnlyTheyWouldSay: "As you wish," meaning "I love you." Former TropeNamer.
* SpellMyNameWithAnS: Westley/Wesley.
* ToThePain: [[RuleOfThree Trope Namer]]
--> '''Westley''': "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."
* UnableToSupportAWife: Why Westley went to seek his fortune.
* WhamLine: "[[SomethingOnlyTheyWouldSay As you wish]]" while falling down the hillside.
* YouFightLikeACow: 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.")

!!Buttercup
!!! Robin Wright

* ArrangedMarriage: To Prince Humperdinck.
* TheBigDamnKiss: "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.
* CatapultNightmare: In the movie.
* CuffsOffRubWrists: After being untied.
* DamselInDistress: 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''.
* DreamingTheTruth: The Ancient Booer.
* EverythingsBetterWithPrincesses: 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.
* [[ThreateningShark Everything's Even Worse With Sharks]]: 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.
* FairytaleWeddingDress: Naturally.
* GreenEyedEpiphany: In the book, the reason she realizes her love for Westley is because the Countess Rugen has the visible hots for him.
* HairOfGoldHeartOfGold
* IceQueen[=/=]DefrostingIceQueen: She flip-flops between these two throughout the book: In the beginning she was an IceQueen, then defrosts after she realizes her love for Westley. She freezes up again after Westley's reported demise, then defrosts after realizing that [[SomethingOnlyTheyWouldSay he's still alive]].
* InformedAttractiveness: 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.
* JobTitle: Her precise function in the story, at least as far as Humperdinck is concerned, is to be a princess and a bride. [[spoiler:And a murder victim.]]
* LadyAndKnight
* MarryForLove
* NeutralFemale: 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.
* OnlyOneName
* PressurePoint: Fezzik uses a Vulcan Nerve Pinch on Buttercup. In the book Vizzini does it.
* ThePowerOfLove
--> '''Buttercup''': "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."
* QuicksandSucks
* RagsToRoyalty
* SoBeautifulItsACurse: 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.
* UglyGuysHotDaughter: 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.
* WorldsMostBeautifulWoman: The book even explains ''how'' she became the worlds most beautiful woman.

!!Inigo Montoya
!!! Creator/MandyPatinkin

* TheAlcoholic: 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.
* BestServedCold: His revenge against the six-fingered Count Rugen for [[YouKilledMyFather killing his father]].
* CatchPhrase:
** JustForFun/{{Hello}}
** MyNameIsInigoMontoya (TropeNamer)
** YouKilledMyFather (TropeNamer)
** PrepareToDie (TropeCodifier)
* DashingHispanic: So dashing, he's the trope picture.
* {{Determinator}}
* DuelingScar: 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.
* ExcuseMeComingThrough:
--> '''Inigo:''' Excuse me...excuse me... Fezzik, please?
-->'''Fezzik:''' EVERYBODY ''MOVE''!
-->'''Crowd:''' *''clears a path''*
-->'''Inigo:''' Thank you.
* FaceDeathWithDignity: When Wesley 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, Wesley is even more good and honorable than he is and rebuffs the very idea of doing so.
* FakeNationality: Creator/MandyPatinkin is not from Spain.
* GoodScarsEvilScars: Has classic good scars in the parallel slashes Rugen gave him to the face.
* HeelFaceTurn
* HeroicSecondWind: He's not going down that easily, Rugen.
* HeterosexualLifePartners: With Fezzik.
* IAmNotLeftHanded: TropeNamer. Pulls this against The Man in Black. Backfires when it turns out the man in black isn't left-handed either.
* IGaveMyWord: 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.
* TheLancer
* MasterSwordsman: Only Westley can equal him in swordsmanshup.
* MinionWithAnFInEvil
* OneManArmy: Humperdink's four elite guards didn't have a chance the second he appeared.
* ParentalAbandonment: His father, Domingo Montoya, was a skilled swordmaker. One day Count Rugen comes to their nice, [[{{Arcadia}} 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, he deems it unacceptable and kills Domingo.
* PhysicalScarsPsychologicalScars: 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.
* PrecisionFStrike: As he [[spoiler:kills Rugen]].
-->'''Inigo:''' I want my father back, you son of a bitch!
* PunchClockVillain: He says it in the film -- "I just work for Vizzini to pay the bills."
* ScrewTheMoneyIHaveRules
* TheSlowWalk: During his final match with Rugen. Justified as he is seriously injured at the time.
* SpellMyNameWithAnS: "Inigo" is the English variant of the Spanish name "Íńigo," so some fans end up using the latter.
* {{Spexico}}
* VillainousBreakdown: A minor example - during his duel with Wesley, after they both stop holding back Inigo noticeably starts losing control of the duel. The more Wesley 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, [[FaceDeathWithDignity he calms down immediately]] [[spoiler: once Wesley disarms him.]]
* WallSlump: During his final match with Rugen.
* WorthyOpponent: Westley.
* YouFightLikeACow: 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.")
* YouKeepUsingThatWord: TropeNamer

!!Fezzik
!!! Andre the Giant

* TheBigGuy[=/=]TheBrute
--> '''Fezzik''': "It's not my fault I'm the biggest and the strongest. I don't even exercise."
* FakeNationality: Although never stated in the movie, in the book Fezzik is Turkish.
* GentleGiant: No, really!
* HeelFaceTurn
* HeterosexualLifePartners: With Inigo.
* MinionWithAnFInEvil
* ParentalAbandonment: His backstory is never explained in the movie but his parents died of a desert plague while they were in Mongolia.
* PlotPoweredStamina: His arms ''never'' get tired.
* PunchClockVillain: 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.
* RhymesOnADime: Fezzik is ''very'' fond of doing this.
--> '''Vizzini''': No more rhymes, now, I mean it!
--> '''Fezzik''': Does anybody want a peanut?
* SmarterThanYouLook: 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 ConservationOfNinjutsu to the Man in Black during their fight.
* ScarecrowSolution: "The Dread Pirate Roberts" rig that Fezzik wears.
* WorthyOpponent: Westley.

!!Vizzini
!!! Wallace Shawn

* CatchPhrase: Inconceivable!
* EvilGenius: So he keeps claiming.
* FakeNationality: Nope, Wallace Shawn is not Sicilian. Shocking, we know.
* IDontPayYouToThink: To Fezzik.
--> '''Vizzini''': "You were not hired for your ''brains''!"
* IKnowYouKnowIKnow: While trying to figure out [[PoisonedChaliceSwitcheroo which goblet contains the poison.]]
-->'''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!...
* JerkAss
* LookBehindYou: Pulls this on the Man in Black in order to switch the goblets.
* TheNapoleon
* NoIndoorVoice
* OutGambitted: Former TropeNamer.
* PlatoIsAMoron:
-->'''Vizzini:''' Let me put it this way--have you ever heard of Creator/{{Plato}}? Creator/{{Aristotle}}? Creator/{{Socrates}}?
-->'''Man in Black:''' Yes?
-->'''Vizzini:''' [[TropeNamer Morons.]]
* PoisonedChaliceSwitcheroo: [[spoiler:Not that it does him any good]].
* SmallNameBigEgo: 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.
* SmugSnake

!!Prince Humperdinck
!!! Chris Sarandon

* AdaptationalAttractiveness: Played by the very handsome Chris Sarandon in the movie, though Westley still calls him ugly, both to his face and to Buttercup.
* AffablyEvil
* AmbiguouslyGay: Prince Humperdinck is the only character not swayed by Buttercup's beauty. [[spoiler: He just views her as a political tool to convince his country to go over war for.]]
* AndNowYouMustMarryMe: The ScarpiaUltimatum version.
* AristocratsAreEvil
* BigBad
* PrinceCharmless: Oh, boy.
* TheChessmaster
* TheEvilPrince
* FatBastard: Only in the novel.
* FauxAffablyEvil
* GenreSavvy
* GreatWhiteHunter: 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 Wesley and Inigo by examining their footprints.
* KarmaHoudini: As the Grandfather points out halfway through the film, Humperdinck lives. [[spoiler:Subverted, as he has to live with the realization that deep down, he is a coward and will always be one. To Humperdinck, a man obsessed with hunting and war, this is a fate worse than death.]]
* KingpinInHisGym: In the book, we first see him wrestling with an ape.
* ProperlyParanoid: "I believe everything to be a trap. It's the reason I'm still alive."
* RomanticFalseLead: Everyone except Count Rugen genuinely believes that he's in love with his bride-to-be.
* ScarilyCompetentTracker
* SuccessionCrisis: 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. [[spoiler: FALSE.]]
* VillainousFriendship: Type I with Count Rugen.
* WickedStepmother: Subverted. His stepmother is actually quite nice, it's just that [[GenreSavvy 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.

!!Count Rugen
!!! Creator/ChristopherGuest

* AffablyEvil[=/=]FauxAffablyEvil
* AristocratsAreEvil
* BeardOfEvil
* CombatPragmatist: 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.)
* CreepyMonotone
* DeadpanSnarker: Towards the completely oblivious Humperdinck.
* TheDragon: To Humperdinck.
* EvenEvilHasStandards: He is a sadist that actually likes to document the reactions his victims have when they are being tortured by the machine, but even he was horrified when Humperdink put the machine up to 50 when it was Westly's turn.
* GoodScarsEvilScars
* MadScientist
* [[NeverSayThatAgain Stop]] ''[[NeverSayThatAgain Saying]]'' [[NeverSayThatAgain That!]]: To Inigo after the latter repeats his [[MyNameIsInigoMontoya Catc]][[YouKilledMyFather h Phr]][[PrepareToDie ase]] one too many times.
* PsychoForHire
* RedRightHand: He has six fingers on one of his hands.
* RoboticTortureDevice: The Machine.
* SoftSpokenSadist
* TortureTechnician
* VillainousBreakdown: 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!"
* VillainousFriendship: Type I with Prince Humperdinck.

!!Miracle Max and his wife Valerie
!!! Billy Crystal and Carol Kane

* AlchemyIsMagic
* AmbiguouslyJewish: Described by Billy Crystal (Max) as a pair of "Jewish trolls".
** [[LampshadedTrope Lampshaded]] in the novel.
-->And so here the point is, if Max and Valerie sound Jewish, why shouldn’t they? You think a guy named [[LiteraryAgentHypothesis Simon Morgenstern]] was Irish Catholic? Funny thing — [[WriteWhoYouKnow Morgenstern’s folks]] were named Max and Valerie and his father was a doctor.
* BerserkButton: Mentioning Prince Humperdinck's name will drive Max up the wall.
* CoolOldGuy: Max.
* CoolOldLady: Valerie.
* HappilyMarried: 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!
* HenpeckedHusband: Max.
--> '''Valerie''': LIAR! LIAR! LIIAAAAR!

!!The Albino
!!! Mel Smith

* EvilAlbino
* EvilSoundsRaspy: 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.
* TheIgor
* PunchClockVillain: He seems to enjoy 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 Impressive Clergyman
!!! Peter Cook

* ElmuhFuddSyndwome
* PunchClockVillain: Brought in to carry out the forcible marriage of Buttercup to Humperdinck. It's not clear how much of this he knows about.

!Outside The Story

!! The Kid
!!! Fred Savage

* HesJustHiding: {{Invoked}}.
--> '''The Boy''': "Wait, what did Fezzik mean, 'He's dead?' I mean he didn't mean dead. Westley's only faking, right?"
* [[IllGirl Ill Boy]]: His grandfather comes to read him the story because he's been extremely sick.
* NoNameGiven
** Though if the book's anything to go by, his name is William Goldman.
* SuspiciouslySpecificDenial: 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'.

!! The Grandfather
!!! Peter Falk

* CoolOldGuy
* DeadpanSnarker
--> '''Grandfather''': Yes, yes, you're very smart. Shut up.
* NoNameGiven
* TheStoryTeller

----