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- In The Princess Bride, at the very end, the Grandson asks the Grandfather to come back and read the story again. The Grandfather replies, "As you wish," which seems very sweet but not particularly dramatic—until you remember what was said earlier: "When he said 'As you wish,' what he meant was 'I love you.' "
- After Inigo Montoya got his Heroic Second Wind, he took control of the duel so thoroughly that he was able to give Count Rugen exactly the same wounds Rugen gave him.
- To explain how smart he is, Vizzini describes Plato, Aristotle, and Socrates as "morons." Maybe if he had spent some time studying the Ancient Greeks instead of belittling them, he would have learned about the art of building immunity to poison.
- When The Man in Black asks Vizzini about the poison, he actually says "Where is the poison?" not "Which goblet has the poison?" Vizzini should have said that he'd drink from the bottle.
- Before their duel Inigo tells The Man In Black that "There's not a lot of money in revenge." Only later do we learn that The Man in Black is the Dread Pirate Roberts, who is actually Wesley and Roberts is a Legacy Character. In the end Wesley suggests that Inigo become the new Roberts. Roberts ship is called the Revenge and there is indeed a lot of money in there.
- Wesley and Inigo are very well matched, both being master swordsmen. However, Inigo is using the sword his father crafted for Count Rugen, the six fingered man. The weight and balance would be slightly different than would be ideal for someone with the standard complement of five fingers. Wesley won the sword fight because Inigo was fighting with a disadvantage the whole time.
- It's also implied that Vizzini's been using Inigo for banditry and bodyguard work. He hasn't fought someone close to his skill in years.
- For all Vizzini's bragging, he's not particularly intelligent, having notable holes in his vocabulary (exclamations and nautical terms). He keeps blathering on about his intellect, but Inigo's nearly as intelligent without effort (and quickly calls him on it in the Trope Namer You Keep Using That Word). How appropriate, then, that his Catchphrase is "Inconceivable!" — not "impossible" or "unlikely," but literally, "who could have thought of that?" He asks this even when he himself is engaged in the same actions he's astounded at.
- Vizzini's also the only person in the movie to die at the hands of The Man In Black, who remarks that Vizzini has a "dizzying intellect," which isn't exactly a compliment.
- Several guards escape the attack on the castle, most notably when Fezzik feigns being the Dread Pirate Roberts. Given that several of Humperdink's guard die during the battle (including Count Rugen) and Buttercup spirited away, Humperdink's in no position to attack Gilder anymore — the Dread Pirate Roberts is too infamous a threat now for the people to stand for it!
- When Wesley and Buttercup first reunite, both have reluctantly taken roles as villains, Wesley as the Dread Pirate Roberts and Buttercup as the fiance to Prince Humperdink. This is reflected in the color of their clothes, red and black, which are often associated with evil.
- Miracle Max rebukes Inigo for his impatience when he and Fezzik bring Westley to him, and warns him that you can't rush a miracle, or you end up with a rotten miracle instead. He then instructs to wait 15 minutes before administering the miracle pill to Westley for it to reach full potency. Later, when Inigo wants to use the pill and Fezzik asks if it's been 15 minutes, he again demonstrates his impatience by telling him they don't have time to wait. This is why although Westley awakens almost immediately, it takes most of the rest of the film for him to fully recover: Inigo rushed the miracle, and used the pill before it was at full potency!
- Although Wallace Shawn is clearly not Sicilian (as Rob Reiner notes in the director's commentary), it's possible that what we're seeing is the grandson's interpretation of the story. He might not know what a Sicilian looks like.
- Humperdink's whole plot is to kill Buttercup and frame Gilder for it to start a war. With the abduction of his wife by mysterious agents, he can still use this as an easy substitute. While Buttercup escapes with her life, Humperdink will presumably still sink two nations into war.
- The guards who escaped will likely spread word that it was the Dread Pirate Roberts who attacked, not Gilder, impairing Humperdink's plan.
- Humperdink's free to live a long life with his cowardice...and try his plan again on another unsuspecting girl. And this time, he'll make sure to pick someone who has no True Love who could thwart him.
- It's implied that Buttercup's captured the goodwill of the people, and that the more intellectual Count was also involved with his plans. Given that Humperdink's castle guard was decimated, and survivors know he's been attacked by the Dread Pirate Roberts, Humperdink can't afford to attack anyone but Inigo for the time being... and Inigo knows full well of Humperdink's cowardice, preventing the prince from pushing too hard.
- As soon as Vissini is hauled onto the top of the cliffs of insanity, he starts cutting the rope. The rope that Fezzick hadn't finished climbing up yet. I know Vissini's a jerk, but thank goodness Inigo managed to help him up in time.
- Vizzini's comment about leaving Fezzik in Greenland isn't just about it being a desolate place — it's inhabited by vikings, who view giants as evil.
- If The Machine took a year off of Westley's life on setting one, how many years will he live to after it was turned to setting 50?