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Bill Ferny was a petty criminal, and I'm not big on him, but he gets his comeuppance via an apple, and so he's not big on the list.

Never liked Ted Sandyman as he seemed to be a 'spoiler' - someone only interested in causing others some grief for personal gain/fulfillment, and generally life's hard enough without others piling on. That and he was dirty yet did not wash.

Gollum was addicted, and so he's a bit easy to pity - there go I but for the act of Frodo? He's evil to be sure, yet at least he's out for himself and so would even turn on Sauron. Gollum was caught by something much bigger and badder than his little wickedness could handle, and still he strove (at times) to turn away from it (like when he caresses Frodo as Frodo is sleeping). He wanted a cure, but could only find it at the bottom of the Crack of Doom as he no longer had the strength to find it alone. And by helping Frodo at the end, technically he's a hero.

Wormtongue is especially loathsome. Unlike Gollum, Worm knows full well what he's doing, which is betraying people who are at least civil to him. Instead of trying to win Eowyn's favor by doing something, he seeks to limit the field and take her by force. Jerk. And though he wants to possess her, he does not love her. If he did, he would let her go...

Saruman isn't as bad. Think that he had a bug when he was first released into ME, and it grew as the Valinor taint wore off - somebody knew something, as Cirdan and Galadriel were never his biggest fans. I think that like Aule he wanted to create creatures of his own, but as he wasn't in Paradise anymore but in the real world, this desire quickly turned to thoughts of domination, control and power. Initially he may have thought of contesting Sauron, but as the idiots who surrounded him weren't very helpful, he realized that he would need to control and order them for their own good as he was the only one with a clue. Unlike Gandalf, he could not allow people to freely choose to serve with him in the manner that they thought best. Think that he was reading some Machiavelli (The Prince) - it is better to be feared than to be loved. And I would add 'easier too.'

Note that the more you try to control, the more that you need to control.

Later, Saruman must have thought that he could accomplish even more if he had Sauron's hordes, and as these Maia had the same first initial, changing logos on uniforms wouldn't be an issue. When his perfect plans didn't pan out, he then became a spoiler too.

Anyway, he too got his just reward.

Moving south, at least Denethor had his people and sons in mind until at the very end, and so I pity him. He wasn't that bad; lost a wife, was losing a kingdom, lost a son, freaked out and sent his other child to a certain death, a Maia was bent on his destruction/downfall (you pick to which one I refer), found out that there's a land of midget people - if that doesn't crack you up, what does it take?

And agree regarding Bombadil's singing and Treebeard's speech. Next page please!