“Sssss” said Gollum, and became quite polite. “Praps ye sits here and chats with it a bitsy, my preciousss. It likes riddles, praps it does, does it?” He was anxious to appear friendly, at any rate for the moment, and until he found out more about the sword and the hobbit, whether he was quite alone really, whether he was good to eat, and whether Gollum was really hungry. Riddles were all he could think of. Asking them, and sometimes guessing them, had been the only game he had ever played with other funny creatures sitting in their holes in the long, long ago, before he lost all his friends and was driven away, alone, and crept down, down into the dark under the mountains.
“Very well,” said Bilbo, who was anxious to agree, until he found out more about the creature, whether he was quite alone, whether he was fierce or hungry, and whether he was a friend of the goblins.
“You ask first,” he said, because he had not had time to think of a riddle.
~ J.R.R.T: The Hobbit: Riddles in the Dark
Hobbits (…) ‘have a fund of wisdom and wise sayings that men have mostly never heard or have forgotten long ago’.
Bilbo’s riddle exchange with Gollum actually falls into the latter category, of things forgotten, for the whole idea of testing by riddles, and some of the actual riddles, come from the ancient and aristocratic literature of the Northern world rediscovered in the nineteenth century by Tolkien’s professional predecessors. (…) Gollum’s riddles, unlike Bilbo’s tend to be ancient ones. Thus his last riddle, delivered when he thinks ‘the time has come to ask something hard and horrible’, derives from a poem in Old English, the riddle game, or more precisely the wisdom testing exchange, between Solomon and Saturn. In this, Saturn, who represents heathen knowledge, asks Solomon, ‘What is it that … goes on inexorably, beats at foundations, causes tears of sorrow … into its hands goes hard and soft, small and great?’ The answer given in SOLOMON AND SATURN is, not ‘Time’ as in Bilbo’s desperate and fluky reply, but ‘Old age’: ‘She fights better than a wolf, she waits longer than a stone, she proves stronger than steel, she bites iron with rust: she does the same to us’. (…)
Gollum’s fish riddle (…) is echoed by a riddle set in the Old Norse wisdom contest in THE SAGA OF KING HEIDREK THE WISE (to be edited many years later by Tolkien’s son Christopher), and has a further slight analogue in a medieval poem from Worcestershire which Tolkien admired, LAYAMON’S ‘BRUT’: in this dead warriors lying in a river in their mail are seen as strange fish. (…) Gollum’s riddles, cruel and gloomy, associate him firmly with the ancient world of epic and saga, heroes and sages.
But Bilbo can play the game too; though his riddles are significantly different in their sources and their nature. Three of them (…) come from traditional nursery rhyme. But where, one might ask, does traditional nursery rhyme come from? Tolkien certainly had asked himself this question (…). In 1923 he had published a long version of the familiar ‘man in the moon’ nursery-rhyme, ‘Why the Man in the Moon Came Down too Soon’ (…). In the same year he published ‘The Cat and the Fiddle: A Nursery Rhyme Undone and its Scandalous Secret Unlocked’ (…).
It may seem surprising that anyone should find nursery-rhymes worth quite so much time and trouble, if it does not quite extend to taking them seriously. But behind all these rewritings and reminiscences lies the philologist’s conviction that, just as the children’s fairy-tales of elves and dwarves had some long-lost connection with the time when such creatures were material for adults and poets, so modern playground riddles and rhymes were the last descendants of an old tradition. (…)
The difference [between Bilbo and ordinary people] is that he has not quite lost his grip on old tradition. Nor, of course, have all ‘ordinary people’. But they have downgraded old tradition to children’s tales and children’s songs, become ashamed of it, made it into ‘folklore’. Bilbo and hobbits are in this respect wiser. [His] unforgotten wisdom puts Bilbo (…) on a level with a creature from the world [of heroic saga and fairy tale] into which he has ventured.
~ Tom Shippey: Author of the Century: The Hobbit: Reinventing Middle-Earth