- City alignments based on AD&D.

Gollum has a complex character... There's a glimmer of good in him that almost manages to win out :) (the episode where the hobbits are sleeping, and he returns from "reconnaissance"); if Sam hadn't insulted him, he might have become a good person...
And Frodo, by the way, became "bad" for a while.
I would say that the problem with D&D alignments is their excessive static nature. But in life, things aren't like that... For example, I was a fan of evil forces until I was 16, and I considered egoism to be the only correct norm of behavior, but now I definitely define myself as good and altruistic...

Well, most characters don't have that many alignments. Only good/evil. :) / :mad:
As for Gollum's "redemption," it's quite far-fetched... You know, it's easy to say "repent," but who would hand over a living person to be torn apart by a giant spider? Imagine it vividly, not just on a theoretical level, and you'll understand: there wasn't much good left in that creature's soul...
As for the "evil" Frodo, let's attribute it to a hypnotic state. Most people lost control when they saw the Ring. Bilbo, Boromir... and even Gandalf admitted that he was afraid of the temptation.

By the way, about Boromir. Gondor, in my opinion, is the embodiment of lawful neutral philosophy. They are not interested in good, but in themselves. Let everyone die, as long as Gondor survives. As Drakolich mentioned in her post, they are "insensitive bureaucrats."