Humperdinck: First things first, to the death.
Westley: No. To the Pain.
Humperdinck: I don't think I'm quite familiar with that phrase.
Westley: I'll explain and I'll use small words so that you'll be sure to understand, you warthog faced buffoon.
Humperdinck: That may be the first time in my life a man has dared insult me.
Westley: It won't be the last. To the pain means the first thing you will lose will be your feet below the ankles. Then your hands at the wrists. Next your nose.
Humperdinck: And then my tongue, I suppose. I killed you too quickly the last time. A mistake I don't mean to duplicate tonight.
Westley: I wasn't finished. The next thing you will lose will be your left eye followed by your right.
Humperdinck: And then my ears. I understand. Let's get on with it.
Westley: Wrong. 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.
Humperdinck: I think you're bluffing.
Westley: It's possible, Pig, I might be bluffing. It's conceivable, you miserable, vomitous mass, that I'm only lying here because I lack the strength to stand. But, then again... perhaps I have the strength after all.
(Dramatic Pause as Westley partially rises and lifts his sword.)
Westley: Drop. Your. Sword.
[Humperdink's sword falls]
"Life is pain, Highness. Anybody who says otherwise is selling something."
— Man in Black
Inigo: I could give you my word as a Spaniard.
Westley: No good. I've known too many Spaniards.
Inigo: I swear on the soul of my father, Domingo Montoya, you will reach the top alive.
Westley: Throw me the rope.
Inigo: You Keep Using That Word. I do not think it means what you think it means.
Inigo: (during a swordfight) You are wonderful.
Man in Black: Thank you. I've worked hard to become so.
Inigo: I must admit that you are better than I am.
Man in Black: Then why are you smiling?
Inigo: Because I know something you don't know.
Man in Black: And what is that?
Inigo: I Am Not Left-Handed!
(later in the duel)
Man in Black: There's something I ought to tell you...
Inigo: What? Tell me.
Man in Black: I'm not left-handed either.
You've fallen victim to one of the classic blunders! The most famous is never get involved in a land war in Asia, but only slightly less well known is this: Never go in against a Sicilian when DEATH is on the line! Ahahaha! Ahahah! Ahahaha—! *drops dead*.
— Vizzini after a failed attempt at tricking the Man in Black
"As you wish."
Grandfather: She doesn't get eaten by the eel at this time.
Grandfather: The eel doesn't get her. I thought I'd mention that 'cause you looked a bit worried.
Boy: I wasn't worried. Maybe I was a little bit concerned, but that's not the same thing.
Inigo: Offer me money.
Count Rugen: Yes!
Inigo: Power, too, promise me that.
Count Rugen: All that I have and more. Please...
Inigo: Offer me anything I ask for.
Count Rugen: Anything you want...