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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.
- Had Vizzini said he'd drink from the bottle, The Man in Black would be compelled to drink both goblets, meaning he'd get a double dose which he might not be immune.
- Vizzini might have an inflated idea of his own intelligence, but his ranting is correct: In turn he says that he can't drink from either goblet, and he was right, both were poisoned.
- 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.
- It's implied that Vizzini's been using Inigo for banditry and bodyguard work. He hasn't fought someone close to his skill in years. Westley, on the other hand, has been engaging in life-and-death combat for the past couple years. Of course he won the duel!
- Similarly Fezzik mentions that he doesn't exercise, indicating that he was born naturally strong; it's likely that, like Inigo, he hasn't fought anyone who could match his strength in a long time either.
- When climbing the Cliffs of Insanity, we see Westley with his sword on his back, rather than on one side. Not only is this more practical for rock climbing, it means he can also draw it from either hand. And indeed, when he draws the sword, he at first puts it into his right hand before switching to his left. Meanwhile, he gets more of a heads up that Inigo isn't left handed, in that his sword scabbard is positioned for a traditional right handed draw. This foreshadowing shows Westley that Inigo isn't a merciless killer and deserves respect, even before the discussion about his father.
- 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, Humperdinck's in no position to attack Guilder 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 Humperdinck. 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.
- Humperdinck has a reputation for being a great tracker, and he shows this off during the search for Buttercup's captors. But in fact, he already knows about the swordsman and the giant, because he hired them.
- In the book, it's easy to see why people would believe that Guilder is responsible for Buttercup's murder. Humperdinck rejected a princess of Guilder after finding out she was bald, so it would be easy for people to imagine that they had his new fiancée killed either to get him to marry her anyway, or just out of spite and revenge.
- The book's frame story is from a middle-aged William Goldman looking back on his childhood, and particularly his father. Goldman (fictitiously) paints his father as a first-generation immigrant from Florin, and by the sounds of it, The Princess Bride, the novel, was the best way that father and son connected. Sharing the book was how they showed affection for one another. There's probably a whole essay to write about how Goldman is drawing off tropes about how immigrant parents and their children connect, or fail to connect. There's a lot of failure in Goldman's frame story— in the present day, he's kind of a sad sack, his family life is awful, he's trying to connect with his own son. (The movie, which came out fourteen years after the book, focuses on optimism, on Billy and his grandpa connecting.)
- There's a gag where Rugen's assistant in the Pit of Despair is introduced with a raspy voice, until a few seconds later when it turns out he just needed to clear his throat. This might be the grandfather trying to give the character a unique voice, but realizes he can't do the rasping without hurting his throat, so he quickly switches to a cockney accent.
- Humperdinck's whole plot is to kill Buttercup and frame Guilder for it to start a war. While our heroes escape, the plan has been thwarted, and Humperdinck has been left humiliated and broken, there's still nothing preventing him from trying the same trick again. Even if he doesn't, he's still the de facto ruler of Florin and will soon be the actual king. How will the nation fare under his direct leadership?
- As soon as Vizzini is hauled onto the top of the Cliffs of Insanity, he starts cutting the rope. The rope that Fezzik hadn't finished climbing up yet. Vizzini presumably knows it's going to take a long time and wants to get a head start on it, but he's being pretty cavalier with Fezzik's safety.