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You never go up against a Sicilian when death is on the line!
~ Vizzini
You fool! You fell victim to one of the classic blunders- The most famous of which is 'never get involved in a land war with Asia'- but only slightly less well-known is this: 'Never go against a Sicilian when death is on the line'! Hahahahaha! Hahahaha....
~ Vizzini, believing he had beaten Westley in their game of wits and suddenly dies laughing from the iochane powder in their wine glasses.

Vizzini is the tertiary antagonist of the 1987 live-action fantasy film The Princess Bride. He is a Sicilian criminal mastermind who is hired by the manipulative and black-hearted Prince Humperdinck to kidnap Princess Buttercup and kill her farmboy Westley. He also hired two men named Fezzik the Giant and Inigo Montoya to help him out.

He was portrayed by Wallace Shawn, who also played Dr. Elliot Coleye and Taotie.

History

Vizzini is the only truly evil member of the trio, as both Fezzik and Inigo opposed the idea of killing Buttercup to start a war (as Humperdinck had told him to do), much to his anger. Vizzini, Inigo, and Fezzik kidnapped Buttercup and took her to the Cliffs of Insanity, where they were pursued by Westley, with the appearance of a Man in Black. When he climbed up the cliffs on a rope, Vizzini cut the rope in an attempt to send him falling to his death, but he held on, so Vizzini told Inigo to kill him if he made it up.

When Westley defeated Inigo in a swordfight, Vizzini told Fezzik to kill him by hitting his head with a rock. Fezzik preferred to fight him without any weapons, and was also defeated. When Westley confronted Vizzini, and Vizzini told him how intelligent he was, Westley challenged him to a battle of wits - he said he put a deadly poison called iocane powder into one of two glasses of wine, putting one in front of himself and the other in front of Vizzini, and told him to drink which one he thought didn't contain the poison. Vizzini tried to outwit him by distracting him then switching glasses, and drank from the glass that was now in front of him. However, Westley had poisoned both glasses, as he was immune to iocane powder, and thus Vizzini was killed when he drank the poisoned wine.