Tailored Riddles and J.R.R. Tolkien

Riddles have played an important role through time. They have been a source of entertainment to some, a tool for education to others, but also a seed of inspiration to the creative minds. Riddles have made their way into many folk tales and stories passed on from generation to generation, as well as into some of the works of very commercial authors.
Probably the most famous series of riddles ever given is the ones in The Hobbit, of the famous author J.R.R. Tolkien.

Riddles were an inspiration for a very important part of The Hobbit

Bilbo vs. Gollum

We all know the story (and for those of you who don’t, this article will contain spoilers): Bilbo Baggins is on an adventure, finds the magic ring and puts it in his pocket, and then, in order to get out of the dark halls and caves beneath the mountains, has a riddling challenge versus Gollum. If Bilbo wins, Gollum will show him the way out of the dark pathways. However, if Gollum wins, he gets to eat Bilbo.

A series of riddles are exchanged. First, Gollum asks:

“What has roots as nobody sees,
Is taller than trees,
Up, up, up it goes,
And yet never grows?”

Click here for the answer.

Bilbo gets it right, and responds with:

“Thirty white horses on a red hill,
First they champ,
Then they stamp,
Then they stand still.”

Click here for the answer.

Gollum gets it and asks him back:

“Voiceless it cries,
Wingless flutters,
Toothless bites,
Mouthless mutters.”

Click here for the answer.

Bilbo in a riddle challenge versus Gollum

Billbo responds:

“An eye in a blue face
Saw an eye in a green face.
‘That eye is like to this eye’
Said the first eye,
‘But in low place
Not in high place.’”

Click here for the answer.

One more attempt by Gollum:

“It cannot be seen, cannot be felt,
Cannot be heard, cannot be smelt.
It lies behind stars and under hills,
And empty holes it fills.
It comes first and follows after,
Ends life, kills laughter.”

Click here for the answer.

And a tricky attempt back by Bilbo:

“A box without hinges, key or lid,
Yet golden treasure inside is hid.”

Click here for the answer.

Gollum gave it another go:

“Alive without breath,
As cold as death;
Never thirsty, ever drinking,
All in mail never clinking”

Click here for the answer.

Bilbo knew the answer, and tried a weapon of his own:

“No-legs lay on one-leg, two legs sat near on three legs, four legs got some.”

Click here for the answer.

Gollum’s last attempt almost got him a nice dinner:

“This thing all things devours:
Birds, beasts, trees, flowers;
Gnaws iron, bites steel;
Grinds hard stones to meal;
Slays king, ruins town,
And beats high mountain down.”

Click here for the answer.

Bilbo almost lost it here, and asked for more time to think, and at that moment got it right.

Then Bilbo asked:

“What have I got in my pocket? “

More of a question, not really a riddle, and the people today are debating if he should have been allowed to ask such a question. Even Gollum complained, however, he did ask for three attempts and that can be taken as a consent that the question is OK.

How is this connected to Tailored Riddles?

This topic and these riddles have been covered in countless websites where fans of the Middleearth debate on whether Gollum was tricked or not. So, how did they find their way to this blog?

Well, if you look at it from a different angle, it does make sense for them to be here. Check the answers to the riddles Gollum gave: mountain, wind, dark, fish, time. It doesn’t take a lot of analysis to see that he has posed riddles about topics that surround him. He lives in the endless dark corridors in the bottom of the mountain, where the wind howls. He eats fish. It is unknown how old he is, as wearing the One Ring gave him longevity.

On the other hand, Bilbo’s riddles were focused on the topics about a careless life in the Shire: teeth, sun shining over daisies, egg, fish on a little one-legged table, man at table sitting on a three-legged stool, the cat gets the bones. As we all know, hobbits love to eat and drink, and have fun around the table. The breakfast is the most important meal of the day for them, followed closely by others. Teeth, eggs and eating fish (and sharing with a cat) are therefore self explanatory. Hobbits are also famous for their gardens, and the Shire is always depicted as a place full of beautiful nature and green meadows – ideal place for daisies being bathed by the Sun.

Other way around

So, both riddlers posed riddles from their own background. But, as luck would have it, supposedly Gollum originally was from a species very similar to hobbits (if not a hobbit himself), and several of these answers he came up with by remembering far back into the days of early childhood. Similar things helped Bilbo – same cultural heritage as Gollum’s meant that he had heard some of these (or similar) riddles as a child, and could work with them.

This is not really how Tailored Riddles work. Tailored Riddles builds a riddle around the person solving the riddles, not around the person posing them. So, following this principle, Bilbo should have thrown Gollum’s riddles at Gollum, while Gollum would pose Bilbo’s riddles back to him. That would have probably made it more fun for both of them. However, we can understand why they decided not to go that way, the object here was not fun, it was a life and death struggle of wits.


After remembering one of the great mind battles of all time, what conclusions are we left with? Well, we would definitely suggest not betting your life on riddles, if you don’t really have to. Riddles are supposed to be fun, a pass time to practice the little gray cells. If you want to try some of that, please create a riddle for yourself. Otherwise, if you want to spend your free time in a different way, go and re-read The Hobbit.

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