I pity Gollum, or Sméagol. But I don't feel any deeper compassion. He was a mean soul before he found the ring, they talk about it. People like that aren't cast out because they're different, they're cast out because they're cruel. I have a feeling that I would have hated Gollum before the ring. But the ring did hurt him (especially in the end). I don't think that the ring would have had such a great affect on Sméagol that within the few minutes after Déagol found it that he decided to choke his cousin right there. But still I pity him, I wouldn't kill him, or at least I don't think so. You can never tell. But pity and understanding is a bit different than friendship and compassion in my mind...
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"Ford! there's an infinite number of monkeys outside who want to talk to us about this script for Hamlet they've worked out!"
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