The Awards Show actually Says A lot About Caine
I feel like people may gloss over the favourite character awards as Caine being self absorbed or hankering for validation, but it's a lot more than that. I think it's Caine's way of giving validation and meaning to the rest of the cast; a way of showing he listens and cares about them that failed rather miserably.
Firstly, you'll notice how he literally decided to half-ass an adventure (they all get guns) in favour for preparing for it. It may not look like he went to prepare for it afterwards; you just see him sitting in a beach chair sipping a drink (turns out he was also preparing for the exit adventure, and also waiting for the adventure to start so he could actually leave). The man's whole schtick is adventures. So the awards show must've been pretty important for him to forsake that.
But what does that have to do with Caine trying to be a good ringmaster? Well, an awards show requires you be attentive to the candidates to judge who should be the awardee. An award show is acknowledgement of some sort of achievement or anything that's celebratory. It's a much more meaningful experience that you can have in a digital world (where one may feel that their experiences are not real (thus, not meaningful) , as gangle has expressed) since its not a simulation or a preset experience or a game of pretend. It has possiblity, thus meaning. Caine decided to go and do something new, to show his circus members that he noticed them and appreciated them.
You can even tell this from the awards he's giving out. We, as the audience,miss most of the awards show because Jax left in the middle of it- but when we are returned to that scene you can here Caine rattling off the last of the subcategories. This is notable on two levels. Caine wouldn't have bothered with subcategories if he'd just wanted to pat himself on the back. Secondly, he actually had reasonable categories and is shown to have actually put thought into who should win. Some may argue that, sure, it's probably the most obvious to us that Zooble gets the award for sailor mouth; but a person who doesn't listen wouldn't notice that Zooble curses and swears the most out of everybody - and it's also important to note that Zooble spends a non-insignificant amount of their time hiding from him. Caine also has been implied heavily to be the one who set the cursing censor in place, which should imply some distaste towards swearing on his part (although he did technically swear in episode 8, it's still debatable whether he considered that swearing when he just declared himself as god) so having him acknowlege that characteristic of Zooble in a positive way is his way of saying 'Looky you! You're an important individual with individual traits! Have a star for that!' The teeth man really listens.
But!! It's still a bad idea on his part. Which takes us to the favourite character award. I need to emphasize that while Caine's intentions to show the cast he listens and pays attention to them, he also has the not-so-hidden desire to be praised and validated through this activity. This can be seen with how he included himself as an option for favorite character. It's not a bad thing! But this did rub the circus members the wrong way. Because Caine himself is the ringleader of the entire awards show, this comes off as self centered and insensitive. Since everything in the circus was made by him and controlled by him, the awards show and the favourite character award feels like a farce, another tedious, ending-already determined 'adventure' that the circus members have to deal with.
Which brings out another point of this. Caine's purpose as the ringmaster of the digital circus is inherently doomed since the people got trapped there. Nothing in the circus feels meaningful, and therefore nothing he does is. Caine is incredibly tone deaf to the desire of leaving the circus. He doesn't seem to understand that they're trapped here, and that their priority in the circus is to escape. He doesn't understand how the people simply can't enjoy his adventures and his activities; because what the circus members want is to go back to their lives, not a emotional rollercoaster of a plot.
So far, what I've gathered is that we have Caine. He genuinely loves the humans placed under his care (however mistakenly). He tries his best to make them happy and wants to receive appreciation for that. He can't, because the game is rigged against him (quite fairly). And he can't fathom why. That's his main flaw; although he really tries to listen and to communicate that, he has the curse of being oblivious. This award show was his way of saying 'You guys are so cool and lovely!!!! Please love me back!!!!'. Unfortunately, he rolled a nat 1 in the perception category, distancing him further from bonding with the humans.
TLDR; Caine is an oblivious little meow meow that tries to win a game rigged from the start that he is also cursed to be disadvantaged at. In his quest to communicate his appreciation, his lack of emotional intelligence causes him to make things about himself.
Edit: please look at this drawing I made of the teeth man












