I'm a sucker for the smart, manipulative villain characters that can pull the strings to get what they want. I like seeing the bad guy be clever and outsmarting everyone, so naturally I'm intrigued by Iago in Othello. His motives are ambiguous but clearly driven by jealousy. However despite being a villain who is lying at face value, when his dialogue gets serious (still in an attempt to manipulate), he speaks in greater truths that transcend our expectation of him as a character.
"O beware, my lord, of Jealousy, it is the green-eyed monster whom doth mock the meat it feeds on. That cuckold lives in bliss Who, certain of his fate, loves not his wronger" he advises to Othello after planting that very seed of jealousy into his superior. This line is insane when you think he is also speaking about himself, its not a stretch to think Iago is self-aware about his unhealthy obsession with taking Othello down. He knows this "green-eyed" monster is destroying him but is willing to take the chance to spread this to the person he wants to take down.
In a story that acts as a warning to the harmful nature of envy and jealousy, it is unnatural, but very compelling, that the most jealous, most evil character in the story is the one speaking the wisest and greatest lessons of dialogue about that theme.
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