Inigo allows the man in black a moment’s rest before they duel, and as he does, he asks the man if he has six fingers on his right hand, as the man who slaughtered his father did. The masked man shows that he has only five. Inigo explains that 20 years ago, when he was 11 years old, a man with six fingers requested a sword from his father, who agreed. The sword was unparalleled in its craftsmanship, but when the six-fingered man returned to claim it, he offered only 10% of his original price. Inigo’s father refused, and the man stabbed him through the heart. Inigo challenged the man to a sword fight and lost. The man spared his life but gave him a scar on each cheek as punishment. Inigo has since dedicated his life to finding the man. The man in black says he hopes he does.
They begin their fight, both showing exceptional skill with their swords, and talk politely as they battle. Inigo praises the man’s skill, but reveals that he is not left-handed and switches to fighting with his right. He corners the man against the cliff ledge, but the man reveals that he’s also been fighting with his non-dominant left hand, and switches to his right as well, knocking Inigo’s sword away. Inigo swings to it via a bar set into the stone archway beside them, and the man follows with the same gymnastic motion. Inigo asks the man’s identity, but he declines to reveal it. They fight on, and the man eventually disarms Inigo. He falls to his knees, requesting a swift death, but the man instead praises his skill and simply knocks him unconscious with a minor blow to the head before running off after Fezzik and Vizzini.
Vizzini, Fezzik, and Buttercup see the man in black coming over the hills in the distance. Vizzini exclaims, “Inconceivable!” yet again and takes Buttercup himself, demanding that Fezzik surprise the man with a boulder to the head when he reaches their current location. Fezzik takes a rock and waits. When the man draws near, Fezzik throws the rock only to scare him, and requests that they put down their weapons and fight with their hands. The man agrees and charges him, doing absolutely no damage to his brute bulk. He dives between Fezzik’s legs and the two make polite small talk as Fezzik hurls several unsuccessful punches. The man jumps on Fezzik’s back and begins choking him. Fezzik slams him into some large rocks, but the man succeeds in choking him unconscious. He checks that Fezzik is still breathing and wishes him a good sleep as he retrieves his sword and runs off after Vizzini and Buttercup.
Meanwhile, Prince Humperdinck and a battalion arrive and survey the footprints where Inigo and the man in black dueled. Humperdinck deduces that the fight’s loser ran off alone and that the winner followed several sets of footprints toward where Vizzini escaped with Buttercup. He assumes Buttercup’s kidnapping was the work of Guilder, and he and his men take off following the winner’s footsteps.
The masked man finally finds Vizzini holding a blindfolded Buttercup at knifepoint at the top of a large hill. The two sit at a flat, table-like rock, where some food and two chalices are laid out. The man slowly approaches and tries to reason with Vizzini, who threatens to kill Buttercup if he comes any closer. The man challenges Vizzini to a battle of wits to the death, which the latter accepts, claiming to be smarter than Plato, Aristotle, and Socrates. The man in black sits and Vizzini pours wine into each of their cups. The man takes them behind his back and returns them, claiming to have poisoned one of them with iocane powder, and asks Vizzini to deduce which one. Vizzini spends several minutes reasoning through which cup to drink from. He momentarily distracts the man and switches the cups around, and then decides to drink the cup now in front of him. When they both drink, Vizzini celebrates having tricked the man into drinking the poison. However, he quickly collapses, dead. The man frees Buttercup and reveals that both cups were poisoned, but that he’s spent years building up an immunity to iocane powder.
Prince Humperdinck and his squadron reach where the man defeated Fezzik. Humperdinck claims that Guilder will suffer greatly if Buttercup dies, and they take off in the direction the man went. Meanwhile, Buttercup and the man run through the open landscape, pausing only for a moment to rest. Buttercup promises whatever ransom the man wants if he’ll release her, but he laughs at her. She says that her prince will find her, though she doesn’t love him. The man accuses her of being incapable of love, and when she claims to have loved more deeply than he ever will, he raises a hand to her as a warning not to lie. They take off running again.
Prince Humperdinck finds Vizzini’s corpse aside the rock with the chalices and deduces that he was killed by iocane powder. He claims he’ll be very “put out” if he doesn’t find Buttercup alive, and he and his men take off again.
When they stop to rest again, Buttercup reveals that she knows the man in black is the Dread Pirate Roberts, and he admits he is. She wishes death upon him, claiming he killed her love. He asks who this love was, suggesting that it must have been some other ugly prince, but she says he was a poor farm boy “with eyes like the sea after a storm.” The man claims to remember killing him, saying he died well, asking only to live so that he may see his beautiful, faithful love again. The man mocks the idea that Buttercup is faithful, however, citing how quickly she got engaged to the prince after learning of Westley’s death. Buttercup is livid, claiming to have all but died when Westley did. They see Prince Humperdinck and his cavalry approaching in the distance, and Buttercup pushes the man down a steep hill into a ravine, telling him to die. He calls out, “As you wish!” as he tumbles, revealing that he is actually Westley in disguise. Realizing this, Buttercup hurls herself down the hill after him. They tumble to a halt, Westley losing his mask as he goes. Atop the hill, the prince surmises that the two are headed into the Fire Swamp, and give chase.
Buttercup and Westley reunite passionately. He asks why she didn’t wait for him, and she says she thought he was dead. They share a long kiss, and we cut back to the young boy’s bedroom, where he now eats a lunch on a tray. He protests having to hear about the kissing again. The grandfather, now holding a mug, says he might not mind it someday. The boy asks to hear about the Fire Swamp and the grandfather continues reading.
Inigo’s story about his father introduces us to the secondary plot of the story: while we’ve thus far understood Inigo as an antagonist (if a likable, compassionate one), we now see that he has a troubling back story that gives his character more dimensionality. We begin to sympathize and even identify with him. His telling this story to the man in black also provides the necessary exposition for his quest to find Count Rugen later in the film.
Purely from a filmmaking perspective, the duel between Inigo and the man in black is one of the highlights of the film. Actors Mandy Patinkin and Cary Elwes spent weeks training with both their right and left hands to perform all the fencing choreography without any stand-ins, resulting in one of the most memorable sword fights in movie history. Their initial design for the battle lasted just over a minute, which failed to satisfy director Rob Reiner, who asked that they make it longer. When all was said and done, the final scene ended up being 3 minutes and 10 seconds long, and took almost a week to shoot from all angles.
This scene, and the two following it in which the man in black bests both Fezzik and Vizzini, provide more examples of characters at odds who nevertheless engage in abnormally polite small talk as they battle. As with the previous example of the man in black hanging off the cliff, this silly banter helps the intense action sequences feel unexpectedly comedic, aiding in the satirical tone of the film and keeping the audience at ease despite the onscreen conflict.
Vizzini’s transparent arrogance ultimately leads to his demise when he engages in the battle of wits with the man in black. His continued use of the word “inconceivable,” even after Inigo points out how much he overuses it, illustrates to us that he needs to appear as intelligent as possible even to the point of hyperbole—claiming to be smarter than Aristotle, Plato, and Socrates, for example, a hard notion to swallow. The moment when he distracts the man in order to switch their goblets is our only direct glimpse into the truth that he brings nothing but nonsense to the table, a fact which is more lost on him than us, as he fails to save himself from drinking the deadly iocane poison.
Viewers commonly don’t understand the man in black’s initial hostility toward Buttercup upon being reunited with her. Upon closer observation, however, it becomes apparent that Westley didn’t realize she believed him to be dead in the first place. After all, there was no proof that he was; Buttercup only assumed so because of the infamy of the merciless Dread Pirate Roberts, who never let other captains live. In Westley’s mind, Buttercup betrayed her promise to wait for him in order to marry into royalty, when in reality it was Buttercup’s depression at the thought that Westley was killed that led her to agree to Humperdinck’s proposal. Once this becomes clear, Westley sees fit to reveal himself to her, screaming “As you wish!” as he tumbles down into the ravine.