Funny error messages in general are pretty annoying to deal with when it's an actual exception as opposed to something relatively simple like an HTTP 404. I admittedly have a bias since I've worked in Tech most of my life and am used to being able to solve technical problems, and it's very frustrating to be told "Whoops! Something went wrong" or "Oh no! There's a problem! We'll dispatch a team of ninja monkeys to fix it!" when all you want is more information. What specifically went wrong? Is it on my side, is it on the website or application's side? What steps can I take to actually fix this, since I've tried again multiple times already?

I'm sure I'm sitting on the wrong side of countless user studies that say to the contrary, but when an exception or problem occurs, I really dislike the feeling of helplessness. Something isn't working the way it is supposed to, and often times I can only rely on myself to fix it; this is particularly relevant for companies with non-existent support services, like Google, where you're basically at the mercy of what other more adventurous and capable users are able to fix on their own. To me, tossing up a "funny" error message when there is no support channel is incredibly frustrating, because not only is there no one I can ask for assistance, I can't even do research myself because I have nothing to go on except for a caricature of the WebDevs or a Frowny-Face and the steps leading up to the problem.

Again, I'm sure I'm on the wrong side of countless studies here, but I can't figure out how this is better than at least some sort of error message.