Interesting question. I've thought about this question before.
Just a brief comment first on what Lalwende said about Bilbo:
Quote:
.....Bilbo to avoid the neighbours.
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With Bilbo, wasn't it really a question of "tricking" his neighbors? There is, I think, one aspect of Bilbo that qualified him as a "trickster", and I've often thought the Ring encouraged this trait in him. Is it a coincidence that the first thing Bilbo does after picking up the Ring is to engage in a Riddle game? Riddling is bright, witty, humorous, and also deceptive. At what point does the humor of sharp wit, which so many of us enjoy, go beyond the kind hearted to become a weapon?
I don't sense this trickster in Frodo; I do sense it in Bilbo. Frodo seems to be a different case (more later, I hope).
I've spoken with some readers who absolutely can not stand Bilbo for this reason. My own feelings on this are different, but I think the trickster element is definitely there.