*slams fist on desk* THANK YOU
And from the other end of things: Gollum is sitting there wracking his brains and dredging up his repressed childhood memories of his dead family that exiled him in order to fairly think up answers to Bilbo's nonsense riddles, Bilbo answers one riddle by accident when he's actually trying to say he hasn't solved it yet, and answers another riddle because a fish jumps out of the lake when 0.1 seconds are left on the countdown clock.
And then Bilbo ends the riddle game by saying. Guess. Just Guess. It worked for me. Why Don't You Just Guess. And the narrative then dunks on Gollum for getting really angry and making an extra guess
It's even funnier in the original version of the book. When The Hobbit was originally published, Gollum was just a one-off guy in a cave and the One Ring wasn't a thing yet, so 1) Gollum offers Bilbo the ring for winning the game. However Bilbo already has it. 2) when the riddle contest ends and Gollum can't find the ring, instead of snapping and trying to kill Bilbo, this happens.
I don't know how many times Gollum begged Bilbo's pardon. He kept on saying: "We are ssorry; we didn't mean to cheat, we meant to give it our only only pressent, if it won the competition." He even offered to catch Bilbo some nice juicy fish to eat as a consolation.
Bilbo shuddered at the thought of it. "No thank you!" he said as politely as he could.
He apologizes for being cheated at the game and having his birthday present (which appears to have been an actual family heirloom in this version) stolen. And then he peaceably leads Bilbo out of the cave and parts on good terms.
And, when JRRT retcons this later to match up with the Hobbit and Gollum's expanded role in LOTR, he claims Bilbo told the original version to obscure the origins of the Ring. So, in-universe, this is the version of the story Bilbo was telling all his friends! The one that includes this line:
"Finding's keeping!" he said to himself; and being in a very tight place, I daresay, he was right. Anyway the ring belonged to him now.
I don't know, man. I think Bilbo has more of a claim on the Ring in the universe where Gollum goes nuts and tries to murder him. At that point he can't just hand it back, you know?
Anyway, after the riddle game of questionable fairness Gollum will go on to
be slightly tortured again but this time by gandalf
be yelled at for telling sam not to make a visible fire in a PvP zone (yes in the book he is primarily angry at Sam for making a cook fire because he's afraid of fire and because they are trying to use stealth, and the culinary disagreement on cooked vs raw rabbits is just salt in the wound so to speak, also sam asked him to go hunt for food to begin with)
be told fairly early on in the plot that Frodo will curse him to commit suicide on order if he steps out of line
If I, wearing it, were to command you, you would obey, even if it were to leap from a precipice or to cast yourself into the fire. And such would be my command.
5. be arrested and wrassled by a whole group of faramir's rangers for the crime of eating fish in the wrong spot when on the point of starvation
6. be told he's an ungrateful turd for being mad when his neck is stiff later from being manhandled
'Have they gone at last? ' said Gollum. ' Nassty wicked Men! Sméagol's neck still hurts him, yes it does. Let's go! '
' Yes, let us go,' said Frodo. But if you can only speak ill of those who showed you mercy, keep silent! '
' Nice Master! ' said Gollum. `Sméagol was only joking. Always forgives, he does, yes, yes, even nice Master's little trickses. Oh yes, nice Master, nice Sméagol! ' [Psst: this is the book version, so Gollum will go on to nearly reach redemption out of warm and fuzzy feelings for Frodo... AFTER this happens]
7. Sam and Frodo are intentionally withholding the fact that they plan to destroy the Ring at the end of this journey.
8. we find out later on that Gollum claims he will die when the Ring is destroyed. as deceptive as he may be, there's no reason to think he does not really believe this. If Gollum does believe he will die when the Ring is destroyed, that means, all of this time, Sam and Frodo have been expecting Gollum to cooperate fully with a long, desperate, difficult journey (that Gollum is in charge of. He's their guide and their survival expert. And they won't even do what he tells them to do in order to not get the three of them killed, see: cook fire, see also: there's a point where frodo just starts running full tilt at minas morgul while gollum just sits there and stares at him in apparent disbelief, also sam gets annoyed any time gollum asks them to do literally anything, also this part where they're just sitting by a toxic waste heap i just think this is funny that they sit down by a toxic waste heap and gollum gets irritated because he doesnt' want to choke to death on vapors)
Too weary to go further they sought for some place where they could rest. For a while they sat without speaking under the shadow of a mound of slag; but foul fumes leaked out of it, catching their throats and choking them. Gollum was the first to get up. Spluttering and cursing he rose, and without a word or a glance at the hobbits he crawled away on all fours.
-and the journey ends in him dying. Inevitably. There was no way to save himself if he was always going to die with the Ring. And they haven't told him this.
At best, Gollum is- under duress!- going through the journey from hell and at the end of it he gets a fun surprise when his most prized possession is destroyed forever, at worst, he's being led to his own execution from minute one.
Gollum probably felt something of the same sort [referring to a long and eloquent preceding paragraph about the agonies Frodo is going through]. But what went on in his wretched heart between the pressure of the Eye, and the lust of the Ring that was so near, and his grovelling promise made half in the fear of cold iron, the hobbits did not guess: Frodo gave no thought to it.
But, to be fair to Bilbo I think 'an eye in a blue face saw an eye in a green face' to mean 'sun on the daisies' is a cool riddle. It's not illogical, just abstract (and it was guessable even by someone who hadn't seen sunlight in 500 years so I think it was fair!)