In what ways are Montresor and Fortunato alike in "The Cask of Amontillado"? How are they different? Compare and contrast.
Both Fortunato and Montresor are incredibly proud men. Montresor quickly identifies pride as Fortunato's one "weak point." According to Montresor, Fortunato "prides himself on his connoisseurship in wine." However, Montresor fails to identify pride as his own weakness. In the first line, he says that "when [Fortunato] ventured upon insult, [Montresor] vowed revenge." Montresor's pride is so highly developed that he cannot endure being insulted without deciding to plot murder. Kind of an overreaction, don't you think? He is clearly incredibly proud if his pride can be so wounded by an insult that he must murder in return. Both men are also "skilful in the Italian vintages." Montresor says that "In this respect [he does] not differ from [Fortunato] materially."
On the other hand, while Fortunato seems a little ridiculous—even his Carnival costume, that of a jester, hints at his foolishness—Montresor is cunning and manipulative. Even while he plots his enemy's "immolation," Montresor had "given Fortunato no cause to doubt [Montresor's] good will. [He] continued, as was [his] wont, to smile in [Fortunato's] face." Moreover, he knows just how to lure the unsuspecting Fortunato to his family vaults: by insisting that he will go to the other local wine connoisseur for help in assessing the wine he recently bought. Montresor knows that Fortunato will not be able to resist humiliating him by revealing that he (Montresor) overpaid for the recent wine purchase. Further, Montresor has thought ahead and brought a black mask and long cloak so that no one will be able to identify him as having been with Fortunato. And he knows that by telling his servants that he will not be home until the morning and that they should not leave the house, this would "insure their immediate disappearance, one and all, as soon as [his] back was turned." Fortunato doesn't even think it's strange when Montresor pulls a trowel out from under his cloak—why would he be carrying a brick-laying instrument?—and he, of course, does allow himself to be led deeper and deeper, to his doom.
Montresor and Fortunato are both Italian gentlemen of high social standing. They are friends, or at least were at some point in the past. Both enjoy wine, and it is this mutual love for the drink that Montresor uses to lure Fortunato into the catacombs. They are also both prideful; an imagined injury to said pride is why Montresor is bent on punishing Fortunato. Fortunato's pride as a wine connoisseur is what keeps him traveling through the catacombs, even when he is unsure of Montresor's intentions. This is where the similarities end.
Montresor is portrayed as cunning and sly, in contrast to Fortunato's rather bumbling drunkenness. He is also obsessed with revenge, revealing a dark side to his nature. Fortunato seems good-natured on the other hand, attempting jokes and seemingly intent on having a good time. He is also guileless and gullible, a bad combination for someone who has crossed Montresor. His jester's costume symbolizes that he will play a fool, while Montresor cape and mask of black silk reveals he will play the executioner.