Othello

Iago decides to destroy his boss, Othello.  He does this by pretending that Othello's wife, Desdemona, is having an affair with Othello's current favorite, Cassio.  In the process Iago also gets his good buddy killed, just for fun.

Iago is widely acknowledged to be one of the single worst scumbags in all of Shakespeare.  As for Othello, sure, there's an element of racism in the portrayal of how easily Othello turns into a "black muslim savage" with Iago's accusations.  But his gullibility is part of his tragic flaw, and Shakespeare can probably be forgiven considering that he had probably seen about two black men at most in his entire life.  The ending is extremely depressing, with an outlook on life almost as bleak as that of King Lear, but there is an element of justice in Iago's fate, and in the end all things are indeed set right.  Part of Othello's problem is that his outsider status makes him insecure and ready to believe Iago's accusations, and Iago knows exactly which buttons to push.  About the whole handkerchief thing : Desdemona lies about having it in order to keep from getting in trouble, which most people have done.  However, as those of us who have told those lies know, when the other person finds out, they are angrier about the lie than they are about what you lied about, and this is also true here.  Tragically, what Desdemona does not know is that Othello already knows that she is lying, so the fact that she lied is her doom.

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