Don't have time to make good and accurate accademic research on this but I LOVE the concept behind Bilbo and Gollum trading riddles, because Bilbo has a sword and he could (even though it's not ideal for him) try to kill Gollum; and Gollum, who appears closer to a beast than to a sentient being, could risk it and attack Bilbo, even if the hobbit's armed: Gollum is, after all, an experienced killer, as we are told in the book, he has killed- albeit in the safety granted by the invisibility power of the ring- much bigger preys than Bilbo, and he has the advantage of being used to the dark. But even in ancient epics, monsters that are somewhat humanoid, while often being considered barbarians- take Polyphemus for example- are still creatures you can somehow talk to and bargain with. Even at their worst, they're still considered beings with the capability for reason, even if an elementary one.
And of course they play the riddle game, which you cannot deny is reminiscence of Oedipus and the Sphinx myth- or an older, archetypical myth for "answer my riddle or you will die". Whether it's the Oedipus myth or some older story, the point is- it's old, it's the oldest challenge in the world that involves using your brain, not your strenght, in that sense it is the least refined and sophisticated game of wits you could play and that's why even someone like Gollum, who's hasn't been outside the Gobiln's caves for God knows how long, knows it and how to play.
In the book it says that he often plays riddles with himself and I think he may do so because that's his one string to humanity, the one thing that stops him from turning into a full beast, who's only concerned with the base needs that we share with animals: eating, sleeping, surviving. The fact that often the solution of these riddles are things tied to Gollum's "human" past (I know he was a hobbit, but I'm speaking of humanity in a broader sense) and in the book it says that it is painful for him to have to remember those days in order to answer Bilbo's riddles is a confirmation of that, I believe. Riddles are his only connection to civility and he refuses to sever it, it hurts him to cling to them as it hurts to be reminded of his past, of food that needn't be hunted or having a connection with other people like him, like his grandmother, people, not preys or predators. Remember that Aristotle's quote, "Man is by nature a social animal; an individual who is unsocial naturally and not accidentally is either beneath our notice or more than human." By asking riddles to himself when is alone, by becoming two from only one, Gollum has created the feeblest form of society and avoided becoming a full beast- even though that society is only made by two people who are the same guy. I really think thag riddles shows that he used to- and maybe at his core still is- a social being.
Maybe even more important and "humanising" than the riddles is the fact that they play a game of riddles, with a set of rules that, as a guarantee, has Bilbo's and Gollum's word of honour. Is that not the most primordial form of a human contract and is "someone's word of honour" not something that only a human could give? You can't ask a animal or a beast for their words: you can certainly build a sort relationship with them, you can train them, you can learn to communicate with them in someway, but there is not such thing as clearly negotiating a pact with them or holding them to a promise.
[I'm not trying to insult animals or deny that we can build incredibly strong bonds with them and find ways to communicate with them (this is the piss on the poor website, I feel like I have to specificate), but you see my point, right? That I am talking about a proper communication and the stipulation of a pact, with rules, consequences and guarantees.]
It's personally something that I always marvel at when I read ancient literature. Often, you see a character represented as a dumb, violent or impolite humanoid as a xenophobic metaphor for barbarians, foreigners, people who do not share the costumes and conventions of the author's civilizations and are therefore considered subhuman, but if they can speak and be held to a promise that is a sign that they are still reasonable beings, that they are human enough.
And that is what Gollum is, human just enough, as much as in the entirety of LOTR everybody tries to dismiss him as a beast because they feel disgusted that may have something in common with that being. Like, Bilbo in the book constantly refers to him as nasty, as something vicious and terrible and wicked but guess fucking what, buddy: you're more similar than you think. Frodo had a point the entire time. I'm sorry, Samwise, but that thing, by ancient literature rules, appears to be a sub-category of a human being.
And I am moderately sure I have a point in all this, because Tolkien was a classic philologist and he sprinkled the Hobbit with reference to old epics to the point "The Odyssey [ytp]" would not be such a far off title. For crying out loud, Thorin puts a tree branch with an end on fire in one of the Trolls's eyes: I think Homer has the grounds for a lawsuit in the afterlife.
And these are the thoughts of a student of classics that loves looking for themes, leitmotifs, parallells, connection and whatever. (I am pretty sure there's something to say also about Bilbo winning the game by cheating, but stumbling into cheating, like he was only saying out loud "the fuck I have in my pocket" and it turned out to be useful, because he is Odysseus if he had 1% of his powers but I haven't thought about it enough to say something new or interesting about it).
Now if we take a step back, and we take off our academically trained hat, Bilbo and Gollum game of riddles might honestly be one of the most hilarious "Bilbo should have died" moment.
Let's forget that Gollum is a narratively human and binded to the conventions of humans in ancient narratives, so he does not comprehend the statement that (quoting the book): "the riddle-game was sacred and of immense antiquity, and even wicked creatures were afraid to cheat when they played at it". Maybe he doesn't even classify as a wicked creature, he is a straight up beast (like many characters consider him to be), or maybe, you know, he is so fucking crazy to the point that his madness doesn't take a step back when it comes to the ancient costume of fair play in riddles challenges. It's not like Bilbo knows for a fact that he can trust Gollum's word. You can never have the guarantee that you can trust a stranger, let's say that you and I agree that Gollum looks a even less trustworthy than your average stranger.
Bilbo wins the game and he is like "Alright, I won, now you need to show me the way out because it's šthe rulesš".
Buddy, you are dead. You are dead before you can even realise you've "won". In which fucking universe the goblin-killer who has developed night vision, talks to himself in the creepiest way possible- the goblins were more eloquent- and has threatened to eat you- not just kill you, eat you- is keeping his boyscout word of fair-play.
Should I believe, Bilbo, that you got more loose screws in your head than Gollum himself? Are you dumb? *takes a huge breath* FOOL OF A TOOK, there is no God of Riddles that would have magically appeared if Gollum dared to break the sacred rules or riddle-making. This is not Jumanji, Gollum's will is not binded by the game to respect its rules.
You are fucked, Bilbo. You are Saruman-at-the-battle-of-Isengard fucked.
As soon as you said "Wrong answer" Gollum could have- should have- leapt at you and strangled you. When what are you going to do, Bilbo? Invoke the rulebook? Pull a John Goodman in The Big Lebowski going "This is not The War of the Last Alliance, there are rules"? You have never held a sword before and Gollum has decades of experience in killing goblins bare-handed. Do you like your chances, Bilbo? 'Cause I don't.
And like, okay, at the end of it all, Gollum does try to kill Bilbo even before he realises Bilbo stole his ring, but to be fair Bilbo cheated at the game. Like the whole "the riddle game is sacred" rings a bit hypocritical after "What have I got in my pocket?".
Personally, I don't think that Gollum trying to kill Bilbo makes him any less human that he sort of is (human can still cheat and lie and kill- they're very good at it, actually), I still firmly believe in the first point that I made, it's just that, push comes to shove, Bilbo had screwed him with an unfair riddle and Gollum is too unused to any kind of relationship that is not predator-prey to let Bilbo go.
All in all, I just think that Gollum is more human that he is given credit for by many characters and Bilbo gives off strong "first character to die in a horror movie" vibes in the way that he deals with Gollum at times.
That being said, this is an analysis of this passage of the Hobbit, not a criticism of the scene. Again, I love Gollum and Bilbo playing riddles and it makes sense for Bilbo try to hold Gollum to his word, since his chances of beating him in a fight are not great. I also think that most 10-year-olds, The Hobbit's intended audience, will think Bilbo is very smart in tricking Gollum and it was a fair request in his side to have Gollum graciously concede the win.
