Ancalagon the Black's pretty cool, simply because he is great, but my vote goes to Glaurung. Why? It's already said here. I need not to add anything.
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"Out of doubt, out of dark to the day's rising I came singing in the sun, sword unsheathing. To hope's end I rode and to heart's breaking: Now for wrath, now for ruin and a red nightfall!"
~Eomer
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