The Hobbit - Chapter 05 - Riddles in the Dark

[Raynor]

What about Gollum's promise if Bilbo won?

Well, that seems to be the weak part in Tolkien's linking the Hobbit to Lotr:

Originally Posted by Letter #109

Rayner has, of course, spotted a weakness (inevitable): the linking. I am glad that he thinks that the linking has on the whole been well done. That is the best that could be hoped. I have done the best I could, since I had to have hobbits (whom I love), and must still have a glimpse of Bilbo for old times' sake. But I don't feel worried by the discovery that the ring was more serious than appeared; that is just the way of all easy ways out. Nor is it Bilbo's actions, I think, that need explanation. The weakness is Gollum, and his action in offering the ring as a present

I wonder if Bilbo was riddling with Smeagol or Gollum?

I doubt that Smeagol the hobbit would fancy eating another hobbit

[JennyHallu]

I doubt Gollum knows that many riddles. I suppose I thought that Gollum set the terms and watched the game, but let Smeagol play. Smeagol wasn't ever gone from Gollum's character, but I think he just never argued until Frodo came into the picture.

[Raynor]

Originally Posted by JennyHallu

I doubt Gollum knows that many riddles.

Well, Gollum wasn't a houseless fea who co-habited Smeagol's body (if that was the case, you could be right) - he was just a part of his fea, a fea which maintained his cohesion and experience.

[JennyHallu]

Part of his fea, yes, but I contend his fea was fragmented. I really liked the way that the movie portrayed his multiple personalities, because it really put into words, so to speak, the impression that I got from the book...Think of a modern day person with Multiple Personalities. One persona may not necessarily have the same knowledge of the other personas.

[Raynor]

One persona may not necessarily have the same knowledge of the other personas.

In The shadow of the past, FotR, Gandalf tells about Gollum in the Misty Mountains that "there was nothing more to find out, nothing worth doing, only nasty furtive eating and _resentful remembering_". Anyway, a Gollum without the knowledge possesed by Smeagol would make a poor survivor, even in the wilds, however small that knowledge may be.

Concerning luck and cheating, I think that the following passages are also relevant(from the Prologue):

In the end Bilbo won the game, more by luck (as it seemed) than by wits; for he was stumped at last for a riddle to ask, and cried out, as his hand came upon the ring he lad picked up and forgotten: _What haw I got in my pocket?_ This Gollum failed to answer, though he demanded three guesses. The Authorities, it is true, differ whether this last question was a mere 'question' and not a 'riddle' according to the strict rules of the Game; but all agree that, after accepting it and trying to guess the answer, Gollum was bound by his promise.