In Othello, where does Iago gain sympathy and appear most unworthy?

Quick answer:

Iago is a despicable human being, who shows his evil nature from the first act. He deceives Roderigo and Desdemona to accomplish his own selfish desires.

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It's difficult to identify any specific point in the play where Iago would genuinely command the sympathy of a reader or audience. His deepest motivations are never really revealed—at least, not in any form most human beings would understand as accounting for the degree of enmity he shows to Othello. But perhaps this mystery is the very thing that prevents some from seeing him as a "conventional" villain. In I, 1, Iago tells Roderigo, "I am not what I am." The whole speech leading up to this has a kind of pathetic quality, and as with all Shakespeare's major characters, the wording is so eloquent that in spite of the reprehensible things he is saying, the audience is lulled into thinking he's making a kind of sense. The one other place in the play where this impression occurs forcefully is at the end. In V, 2, when confronted with the consequences of his deception, Iago calmly says,

Demand me nothing. What you know, you know.
From this time forth I never will speak word.

This silence clinches the ongoing mystery, the blank at the center of Iago's soul. We are left to wonder if this man is human at all—he seems like an automaton that carries out its actions without rational (or even irrational) motivation. And yet, virtually every other appearance he makes shows the unremitting hatred in his behavior, including the vicious racist attitude he expresses against Othello. On balance, there is much more shown to us as unworthy and negative about Iago than sympathetic in any way.

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Iago is such a fascinating character who equally repells the audience but also attracts them. What is so interesting about him is the way that he, like Richard III and other Shakespearian villains manages to inspire trust and confidence in those around him in spite of his clear and obvious villainy. Perhaps the scene that inspires sympathy most in the audience is in Act I scene 1, when Iago describes how he was not selected for promotion, in spite of being favoured, an Cassio, a man who lacks the experience of Iago, was selected instead. Iago's judgement that Cassio is "mere prattle without practice" is an argument that presents his annoyance as being justified.

Perhaps the moment in the play when Iago appears most unworthy comes in Act V scene 2 when he kills his wife in front of an audience. Gratiano communicates the intense shame that his act shows when he says "Fie! Your sword upon a woman?" Certainly the way in which Iago attacks the defenceless Emilia, calling her "villainous whore" and stabbing her before fleeing earns him nothing less than the audience's complete lack of favour and disgust. This is the point when any allure Iago's character once had has now well and truly disappeared and his evil characteristics have manifested themselves well and truly.

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