Cursed items?

[Kafkonia]

Pete Shandor, Human Cleric of Luck and Chaos, had an interesting relationship with the magic item salesman the party frequented in their hometown, always trying to see if he had a "discount magic item" bin with cursed or malfunctioning items. Eventually Pete got a nice deal on a cursed Hat of Disguise -- the illusions it got were almost right, but not quite.

Never before had the orcish ladies in the dungeon seen an orc in a stylish leisure suit and platform shoes. But thanks to some good rolls on Bluff, followed by a couple of Dex checks and Fort saves, Pete and his half-orc buddy managed to, uh, 'defeat' the encounter without recourse to violence.

 

[Harmon]

Couple I have thought about-

Ring of Invisibility - It could not be removed. It made you invisible to anyone but those you wanted to be invisible against.

Cloak of Devouring - see Bag of Devouring

Helm of Limited Underwater Action - functions like a Helm of Underwater Action for just about long enough to need it then no longer.

Bad Gold Piece - Any time you go to buy something the merchant whom you give gold to counts the coin and finds you shorted him by 20%. Even when you get rid of all of your gold this one sticks to you.

The Helpful Imp - Finguring of Wonderous, t'is an Imp that befriends and "helps" you, by assisting the flanking of your foes, and whispers "oh, that is a good lie boss," when you are trying to report to someone you want to be honest with. The Imp is really trying to help. Killing him will not remove him, only a Remove Curse.

A Dagger that couldn't be dropped, released, or otherwise gotten rid of by any means.