My favorite meme magic item was the Ring of I Am Ugly. Someone used the 3e magic creation guidelines (this word is not important, guidelines means whatever it says, I'm specifically allowed to do in all circumstances, dictionaries can't be trusted) to create a ring of cure minor wounds at will. And it was very, very cheap and we were very, very low level. Which meant as long as you had 1 round per hp you had access to unlimited out of combat healing. One of the characters who used it was a "your charisma is what?!" charismagic diplomancy sort. It was just a wacky all in good fun sort of thing.
Imagine a half harpy half goblin inspired by a Xanth character with a charisma of YES who's entire character motivation was to be pretty and see all the other pretty people and places (Which was everywhere and everyone who wasn't a jerk. There were only different kinds of pretty, some of which they didn't get, but that was okay. Not as pretty as THEM of course, but pretty all the same.) trading the ring with a gruff vaguely hostile monk who's bottomed out charisma translated as them not understanding weird concepts like not spitting loogies on the royal floor during negotiation taking turns chanting "I am ugly" as an activation phrase over and over as part of a "healing trance". The whole party were bizarre one dimensional caricatures who had no business adventuring together. I've learned so much about being a better player and dm (among other things) since those days, but they make for some bizarre amusing stories.
