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  “Gandalf, Gandalf!  Good gracious me!  Not the wandering wizard that gave Old Took a pair of magic diamond studs that fastened themselves and never came undone till ordered?  Not the fellow who used to tell such wonderful tales at parties, about dragons and goblins and giants and the rescue of princesses and the unexpected luck of widows’ sons?  Not the man that used to make such particularly excellent fireworks!  I remember those!  Old Took used to have them on Midsummer's Eve.  Splendid!  They used to go up like great lilies and snapdragons and laburnums of fire and hang in the twilight all evening!”  You will notice already that Mr Baggins was not quite so prosy as he liked to believe, also that he was very fond of flowers.

In this excerpt Tolkien lists some stories Gandalf had told. Some seem like generic fairy tales, but the last one seems like it might be a reference to another story he wrote.

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    It's nothing more than a nod to a very old and long established trope in faery tales, the protagonist often being a woodcutters son or widows son (the point being that they are forced to 'go seek their fortune' because they are poor and otherwise have no prospects), a widows son being a popular choice because of course as the traditional breadwinner in the family is lacking so no further explanation of why the boy comes from a poor family and must seek his fortune is needed in these traditional tales, it's nothing more than that ..
    – Pelinore
    Commented Feb 4 at 3:28
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    another popular faery tale trope is the uncommon virtue of the third or youngest in any set (princes, brothers or sisters, Cinderella is the third sister you'll note, little pigs, billy goats, even bowls of porridge and beds), I was almost surprised he didn't throw that one in as well ;) which is always the most worthy, the elder or preceding two always seemingly having some fault in their character .. it's just a humorous reference to, an easter egg if you will, and acknowledgement of one of several very common faery tale tropes.
    – Pelinore
    Commented Feb 4 at 3:43

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The poor boy in fairy tales can indeed be a widow's son and have, of course, extraordinary luck so as to end up married to the princess. A number are noted in British fairy tales:

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Two widow's sons are resurrected in the Bible : one by Elijah and one by Jesus - a fact which Tolkien would have been well-aware. That might be the source of the idea of the lucky widow's son.

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    Tolkien himself was a widow's son, and in 1918 the only survivor of his circle or friends.
    – Anton Sherwood
    Commented Feb 4 at 23:43
  • And why would widows' sons have unexpected luck, if there were no such a being as Eru at work in the world?
    – EvilSnack
    Commented Mar 18 at 23:00

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