In the woods, Prince Humperdinck and Count Rugen discuss how Humperdinck hired Vizzini to kidnap and kill Buttercup so he could frame Guilder for her death and start a war. Now, though, he plans to kill her on their wedding night to incite the same outcome. Rugen opens a secret door in a large tree beside them via a knob on its trunk and invites the prince down into the Pit of Despair. The prince declines, citing his heavy workload, and says goodbye. In the pit, the pale man straps Westley to The Machine, a device designed to suck the life out of its victim. Rugen sets it to the lowest setting, and a slot opens to allow water to rush over a water wheel, turning the machine’s parts and causing Westley to groan in agony. They let him suffer for a minute and then turn the machine off again. Rugen claims to have just sucked away one year of Westley’s life. Claiming to be writing a book on pain, Rugen asks Westley how he feels, but Westley responds only by sobbing.
In his office, Prince Humperdinck peruses piles of paperwork. His Chief Enforcer Yellin comes in, and Humperdinck tells him that invaders from Guilder have infiltrated the nearby forest of thieves and are planning to kill Buttercup on their wedding night. Yellin expresses skepticism, but they’re interrupted by Buttercup asking if there’s any update on contacting Westley. Humperdinck asks her to be patient, and she reminds him that Westley will come for her and leaves. Humperdinck demands that the Thieves’ Forest be emptied and its inhabitants arrested on day of the wedding. Yellin worries that he won’t have the numbers to overcome the thieves’ resistance, but Humperdinck angrily tells him to form a brute squad and see it done.
On the day of the wedding, Yellin’s men carry out the daunting task of rounding up the hundreds of thieves inhabiting the forest. A drunk Inigo Montoya refuses to move as he rambles about waiting for Vizzini at the spot where they were originally hired to help kidnap Buttercup. A soldier enlists the help of Fezzik, who is on the brute squad, but he instead knocks the soldier unconscious and greets Inigo fondly. He nurses him back to sobriety and tells him of Count Rugen, the six-fingered man up at the castle, but says that the castle door is guarded by 30 men. Inigo, admitting his inability to strategize, claims to need the help of the man in black, who bested Fezzik, Vizzini, and himself, to get inside to kill Rugen. He runs off to find him.
Humperdinck sharpens a dagger in his office as Yellin comes in to report that the Thieves’ Forest is empty and the door guarded by 30 men has only one key, which Yellin will keep on his person. Humperdinck tells him to increase the guards’ number to 60. Buttercup comes in and Humperdinck proclaims that they’ll soon be married and off on their honeymoon around the world, accompanied by every ship in his armada. Buttercup realizes that having every ship present means that he didn’t send his four fastest to seek out Westley. She is nonetheless confident that he will come for her. She calls the prince a coward and says that he can never break the true love she and Westley share. This enrages him, and he locks her in her room and runs to the Pit of Despair, resenting Westley so much that he throws The Machine’s setting to its highest, prompting even Rugen to protest. Westley shrieks helplessly in agony as Humperdinck, Rugen, and the pale man look on. His screams echo throughout Florin, heard by the townsfolk, Buttercup in the castle, and Inigo and Fezzik as they search for him. Inigo recognizes the screams as the same ones that his heart made when his father died, and they follow them into the forest.
They come upon the pale man rolling a wheel barrow, and Inigo threatens him at sword point. Fezzik attempts to jog his memory with a bop to the head, but hits him too hard and knocks him unconscious. Inigo kneels and calls upon the soul of his father to point his sword toward the man in black’s whereabouts. The sword moves to the nearby tree. Inigo thinks this is a dead end, but when he leans on the secret knob in defeat, the entrance to the Pit of Despair is revealed. Inside, they find Westley dead on the table. The boy interrupts to ask if Westley is actually dead, and we return to his room. He wants to know who kills Humperdinck at the end, but the grandfather says that Humperdinck lives. This upsets the boy, and the grandfather stands and suggests that they stop so as not to agitate his illness. The boy relaxes and asks him to sit and keep reading, which he does.
Back in the pit, Inigo and Fezzik take Westley’s body to a miracle worker in the woods named Max, who once worked for the king before Humperdinck fired him. Max initially shoos them off, saying he’d probably kill the client since the prince obviously didn’t trust his competence, but when Inigo tells him that the man is already dead, he agrees to take a look. They lay him out on the kitchen table, where the man inspects him and finds that he’s not completely dead, just “mostly dead.” He inserts a large bellow into Westley’ mouth and pumps him full of air. He yells at Westley about why he wants to live, and upon pressing on Westley’s chest, Westley groans out a barely audible, “true love.” Max pretends to have heard something else, but his batty wife comes in and lectures him about selfishly not wanting to help someone who’s truly in love. When Inigo interrupts to say that Westley’s survival will mean saving Buttercup and humiliating Humperdinck, Max stops and agrees to help, wanting revenge on Humperdinck for firing him. He and his wife give the men a small pill covered in chocolate, saying to wait 15 minutes before administering it, and send them off.
Inigo and Fezzik carry the still “mostly dead” Westley up to the castle and observe the now 60 guards protecting the castle door. Inigo is undeterred since they have the man in black to help them, and they prop him up and feed him the miracle pill. He awakens immediately, but can’t move his body yet. Inigo explains their situation and Westley says that there’s no way for the three of them to best 60 men with no time to plan, unless they had a wheelbarrow and a holocaust cloak. They remember that the pale man had a wheelbarrow outside the Pit of Despair, and Fezzik reveals that he took a holocaust cloak from Max’s house. Meanwhile, in the castle, Prince Humperdinck helps Buttercup put on a necklace, saying she should be excited to get married. Buttercup still believes that Westley will come for her and clarifies that she’s not getting married.
In section 4, we’re finally fully introduced to the character of Count Rugen, and we quickly realize that he may be the nastiest antagonist in the film. Not only do we learn that he’s the six-fingered man that killed Inigo’s father and later takes glee in trying to kill Inigo himself, but he also carries out Westley’s torture with a twisted, pedagogical tone, noting his pain for posterity with a sick sort of calm. Humperdinck is prone to hilarious understatement, and Vizzini is a complete caricature, but Rugen is the only character whose villainy provides no comedic effect. Instead, it just makes you hate him. This serves as an effective build-up to the satisfaction of seeing Inigo take him down later on.
Though Buttercup falls victim to Humperdinck’s deception and then realizes her mistake in trusting him, she never loses faith in Westley’s promise that he will always come for her. As covered in the previous section’s analysis, Buttercup isn’t much of a hero to root for, as she is constantly being pushed around and saved by others, but one of the few areas where she is truly likable is her unwavering bravery and faith in her love for Westley. Had Humperdinck chosen another girl to marry, that girl might not have put up such a fight, but Buttercup displays her stubbornness and determination right in Humperdinck’s face, leading to the only time in the film that he loses his cool and grows genuinely, unfunnily angry.
The fact that Westley knocks both Inigo and Fezzik unconscious only for them to later aid in his revival is ironic in many ways. Firstly, it provides a turnaround by which enemies unexpectedly become friends. After all, despite their initial role as antagonists, Inigo and Fezzik are shown to be compassionate, working under Vizzini mostly because they have no choice, and this paves the way for the audience to root for them, such that when they get their shot to play for the good guys in the latter half of the film, the audience is completely on board for them to take it (by contrast, had Vizzini or Humperdinck had such a change of heart, we might've been more hard-pressed to forgive them). Secondly, there is irony in the direct parallel of the two men whom Westley knocked unconscious now returning him from a similar state. Their roles are reversed and Westley is now the unconscious one. Finally, Westley's choice to show mercy upon the men by not killing either when he had the chance allows for karma to be on his side as they subsequently show mercy on him. Had he successfully killed them, he would've died as well, as there would've been no one to bring him to Miracle Max and save his life.
Max and Valerie’s single scene in the film is one of the most beloved by audiences for its sheer hilarity and ludicrousness. Billy Crystal and Carol Kane were both well-established comedic actors in 1987, and their small cameos as these batty miracle workers only drives home how fun and lighthearted The Princess Bride is meant to be. In interviews about the film, Mandy Patinkin (who played Inigo) recalled that the only injury he sustained while filming was a bruised muscle in his rib cage from stifling his laughter while acting opposite Crystal. Director Rob Reiner was even reported to have left the set during filming at one point, as he was worried that the microphones would pick up his laughter and ruin the shot. When the characters’ situation looks most bleak, with Buttercup helplessly trapped and Westley seemingly dead, Max and Valerie come on the scene to bring our spirits back up and save the day.
And if that weren’t enough to remind us of how silly this story is meant to be, Westley proposes a plan to get into the castle with a wheelbarrow and holocaust cloak, only to discover the albino had a wheelbarrow and Fezzik—for absolutely no discernible reason except convenience to the plot—took a holocaust cloak from Max’s house. This absurdly convenient set of circumstances continues the film’s parody of overcoming impossible odds and saving the day even after it seems impossible to save—indeed, they’ve already brought our deceased protagonist back from the dead; why shouldn’t they now have the exact two items they need to ensure a happy ending?