Tolkien's Funny Bone

[Hookbill the Goomba]

I've often considered this topic rather closely and a few things have sprung to mind.
I think that Tolkien found that little folk being greedy was rather amusing, you can see this in the Hobbits. His word play here and there will say something like "No one refused a second helping, or a third or even fourth!" That always amused me, anyway. Even old Gandalf says, "Hobbits would gladly sit on the edge of ruin and discuss matters of the table and the small doings of their great grand fathers to the ninth degree."

I also think he liked putting the 'well-to-do' in situations that they wouldn't like to be put into. Bilbo is a prime example of this, as we see in The Hobbit, he is (in Tolkien’s own words) rather well-to-do and had no desire for any adventures (save in his Took nature). The number of times his mind wanders onto his old Hobbit hole (as well as good food, of course).