The character of Smeagol/Gollum is iconic, and makes a much delayed entrance into the book here. Riddles in the dark was one of my favorite chapters in the Hobbit.
When Gollum finally appears, I realized how notable Gollum's absence for over half the book was. It's amazing what Gollum does to pepper up a story where some of the chapters have really dragged. The entrance is delayed, but when it comes it's a true delight. It's foreshadowed properly as well--Gandalf and the Company mention that someone is following them numerous times throughout the book.
There's one scene worth mentioning before Gollum. I still remember the rope scene, where Sam bemoans the loss of the rope by tying it. He gives it one last tug lovingly, and the rope falls. Frodo jokes (and half says it seriously) that he was foolish to trust Sam's knot. Sam takes it as a personal affront. It's a lovely scene, and something that really helps to establish character. Sam becomes one of the best developed characters in the story, and it's scenes like this that really help flesh him out.
Gollum's reputation, of course, precedes himself. When Gollum appears, the Hobbits overpower him, and Gollum weeps. Frodo takes pity on Gollum, and follows Gandalf's advice and shows mercy. Sam, of course, doesn't trust Gollum, and makes that very clear. This is another great way that Tolkien brings characterization. Frodo (foolishly) seems to trust Gollum whole-heartedly, and Sam doesn't buy Gollum's act for a moment.
When Gollum wishes to swear on The Precious, Frodo's corruption shows for a moment. Frodo will not allow it. Period. It's little things like that over the course of the book that hint at Frodo's final decision at Mount Doom.
One thing I always wondered: would Sam had claimed the Ring as his own? Sam, with Frodo the whole time, seems completely immune to the Ring. Even when Sam is reluctant to hand the Ring to Frodo later on, it's not because Sam wants the Ring for his own. It's because Sam is concerned about handing another dose of heroin to a junky who demands it.
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