5 worst characters... how about I list the five most frustrating characters? The thing I find most frustrating, is the refusal to repent, even when the chance is clear. WIth that in mind:
Denethor, for obvious reasons
Gollum; he came so close that day in the tunnel, and poor Sam didn't know the damage he did; poor Smeagol...
Saruman's refusal to repent when Gandalf offered him the chance on the steps of Orthanc; and likewise his refusal to repent during his confrontation with Frodo
Feanor; I really like him as a craftsman and artist; even Gandalf wanted to watch him at work; and his warring and stiffnecked attitude makes me sad
Thingol's stubborn attitude towards Beren and Luthien, and his refusal to listen to Melian's advice and her warning.
In The Hobbit, all those stubborn kings who let the greed get to them--Thorin, Thranduil, Bard... twinkies all.
I never understood it when I was younger, but Galadriel's passing the test means more and more to me as the years go by.
I love Boromir's repentance.
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...down to the water to see the elves dance and sing upon the midsummer's eve.
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