Usually when I hit an error page, and especially if I hit repeated errors, I'm not in the mood for fun, and I'm definitely not in the mood for "fun" provided by the people who probably screwed up to begin with. It comes off as "oops, we can't do anything useful, but maybe if we try to act cute you'll forget that".

Also, it was more fun the first time or two. There's a not a lot of orginal fun on the error pages you get nowadays.

> People love dreaming of the 90s wild web and hate the clean cut soulless corp web of today

It's been a while, but I don't remember much gratuitous cutesiness on the 90s Web. Not unless you were actively looking for it.