At what point in the story, "The Cask of Amontillado," is Montresor the most disturbing?
Ultimately, this is an opinion based question. Different readers might find Montresor more disturbing at different parts of the story. I also suppose that this answer might change depending on if it is the reader's first time through the story or not. I've been through this story many times, and I am quite disturbed early on by Montresor. The line that I am thinking of is the following line.
I was so pleased to see him that I thought I should never have done wringing his hand.
I know that Montresor plans to kill Fortunato. Montresor knows it at this point too. What I find disturbing is that Montresor is pleased with seeing Fortunato. Montresor is excited about what he is going to do. Additionally, Montresor is completely able to mask all of his intentions and give his victim no hint of what is going to happen. Everything about Montresor at this point supports the notion that he is a psychopath. The following passage is from Psychology Today, and it describes Montresor perfectly.
Psychopaths, on the other hand, are unable to form emotional attachments or feel real empathy with others, although they often have disarming or even charming personalities. Psychopaths are very manipulative and can easily gain people’s trust. They learn to mimic emotions, despite their inability to actually feel them, and will appear normal to unsuspecting people. Psychopaths are often well educated and hold steady jobs. Some are so good at manipulation and mimicry that they have families and other long-term relationships without those around them ever suspecting their true nature.
When I think of Montresor as a psychopath, I begin to think that Fortunato is not Montresor's first victim. Everything about Montresor's execution of his plan is near flawless. The events of the story feel practiced, and that is what I find very disturbing about Montresor. He's an efficient murderer, that seems experienced, and shows no remorse.
There is a moment in the story when Montresor seems to hesitate and second guess his plan.
For a brief moment I hesitated, I trembled.
I do not believe that Montresor is hesitant about killing Fortunato. I think he hesitates because he is concerned that the plan isn't going 100% the way it was originally planned out. Fortunato wakes up before the wall is complete. I don't believe that was part of the plan, but it ends up giving Montresor even more pleasure in the deed.
I placed my hand upon the solid fabric of the catacombs, and felt satisfied. I reapproached the wall; I replied to the yells of him who clamoured. I re-echoed, I aided, I surpassed them in volume and in strength. I did this, and the clamourer grew still.
I find this part very disturbing as well. Fortunato is begging for his life, and Montresor seems to be mocking those screams. That's definitely sick and disturbing.
In a uniquely dark vision, Edgar Allan Poe probes the mystery of the self in "The Cask of the Amontillado." The unreliable narrator, so characteristic of many of Poe's tales, becomes increasingly perverse as the narrative continues. His use of reverse psychology to lure Fortunato into the catacombs and his double entendres upon such words as "mason," and later words with sexual connotations increase the horror of which Montresor is capable.
As he leads the unsuspecting Fortunato into the remote end of the crypt, Montresor "seduces" his enemy into being fettered to the wall. There is a perverse use of words that suggest that Montresor enjoys a certain sado-masochistic pleasure in walling in his foe.
It is, then, after Montresor finishes his mason work, that he is the most disturbing as he replies to the shrill screams of Fortunato by "unsheathing my rapier" and groping within, then screaming and "surpass[ing] them [the screams of Fortunato] in volume and strength." When a low laugh emanates from the niche in the wall, Montresor describes the effect upon himself as "erect[ing] the hairs upon my head."
No answer still. I thrust a torch through the remaining aperture and let it fall within....My heart grew sick--on account of the dampness of the catacombs.
Here, the real horror lies within the cold-blooded and perverse mind of Montresor.