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).
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.
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. *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: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.
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 se 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: Probably, although a popular fanon joke is that prior to reuniting with Buttercup, he spent several years raping and 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.
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."
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.")
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.
Dumb Blonde: In the book. She's a little smarter in the movie.
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.
Ice Queen/Defrosting Ice Queen: She flip-flops between these two 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.
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.
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."
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.
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.
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.
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.
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.
One-Man Army: Humperdink'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, he deems it unacceptable and kills Domingo.
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.
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 Wesley and Inigo by examining their footprints.
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, but even he was horrified when Humperdink put the machine up to 50 when it was Westly's turn.
And so here the point is, if Max and Valerie sound Jewish, why shouldn’t they? You think a guy named Simon Morgenstern was Irish Catholic? Funny thing — Morgenstern’s folks were named Max and Valerie and his father was a doctor.
Berserk Button: Mentioning Prince Humperdinck's name will drive Max up the wall.