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I may say something a little out of the ordinary, but I think that the worst thing Frodo faced was not the Ring itself, but rather the 'knowledge' that even if he saved the Middle-Earth he would not be alive to enjoy it. Up until the last moment when he hesitated due to the power of the Ring itself, he was willing to sacrifice himself and probably his best friend to save The Shire and everyone else he loved, even when he 'knew' he would not be there to enjoy it.
Ultimately he was saved by the Eagles if I'm not mistaken, but even then I got the feeling that although he did survive his Quest, his outlook on the world had changed and he never felt trully happy (at least until he reached Valinor, that I don't know)
Also, I would like to offer my view of the worst thing that one of my favourite characters had to endure. And I'm guessing you will both agree with me and admit that you had never thought about it before (yes, I'm getting cocky)
But I believe Fangorn (the Ent 'leader') had to face a terrible choice. His people were not used to make any kind of "rush" choices yet they decided to confront Saruman in "a hurry" I believe that for him and the other Ents making the choice of going to War in such a short time for their standards must have been a REAL difficult one to make.
Hope I got you thinking over that one!! if not, at least I tried
Farel
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