The bad entity that gets my vote would be Glaurung the Dragon. While I realize he was created of/made by/ born of Melkor, his destruction of Nargothrond and his subsequent dealings with the children of Hurin -- turning them incestuous! -- was one of the truly sick and mischievious deeds ever conducted throughout the entire History of Middle-earth. It took a truly blackened heart to do such a deed. I vote it the most evil deed done by the most evil creature.
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"I wish I could go all the way with you to Rivendell, Mr. Frodo, and see Mr. Bilbo," said Sam. "And yet the only place I really want to be in is here. I am that torn in two."
"Poor Sam! It will feel like that, I am afraid. " said Frodo. "But you will be healed. You were meant to be solid and whole, and you will be."
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