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Do you guys like that stuff? Like when your browser crashes with an "Oopsie!" or you visit a 404 page and it tries to be funny about it. Bonus points if it shows an anime-like chibi character that's supposed to make you sympathetic I guess? For some reason that kinda pisses me off. I think I prefer simple informative messages that tell me what happened in a formal tone.
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Take Doom for example. I like a lot how it says "Next time you come back here Ill be waiting with a bat" when you want to quit or "I'm too young to die" for easy or "Are you sure? This skill level isn't even remotely fair." Something about that seems to be aware that the target audience probably doesn't know much about how the game works internally so it speaks in the language the user would understand.
Yeah, but your examples are intentional and serve their narrow and benign purpose. Imagine if chocolate-doom crashed with "a cacodemon ate all your visplanes". Or perhaps in tune with the original messages, "you should've gotten more plats, loser". It's being cheeky in the wrong situation.
I think that at least for big mainstream websites, cutesy error messages are not worth the potential trouble. I remember a while ago a thing about a Buzzfeed article about some serious topic - a massacre or whatever - where it had embedded media that was broken or had a bad url and so in the middle of this serious article about death Buzzfeed showed its default cutesy error message like "oopsie! we has a sad 😭"