I haven't had time to read the whole thread but so far nobody seems to have mentioned Denethor. I find that he is a sad character. I pity him because he has fallen so far. In his younger days he was a brilliant steward but he ended up being corrupted by Sauron. Not only that, he went mad as well. As if that wasn't enough his favourite son had to be killed as well.
Of course Gollum is an obvious choice and thus Denethor becomes forgotten. Bu another character I pity is Saruman. At first he was good but in the end he has become almost as evil as Sauron. However, if he had stayed at the good side of things he could have achieved so much more.
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