Encounter: seventh-level Paladin cursed to appear with the form of a big ol pupper in a rainbow propeller beanie
Item: KITCHEN GUN; while usable as a standard firearm, any item or creature shot thrice is also magically cleaned and spotless, aside from the three bullet holes. Probably some ooze monsters and undead this would be great against
Encounter: some adorable cyborgs from the future (source)

Item: prosthetic leg that grants the wearer several of a woodpecker’s adaptions: a head that is 100% proof against bludgeoning damage, and the less-useful ability to deliver headbutts at a rate of 20 per second. Might have limited appeal since you have to actually replace a leg with it, but hey, how many axe-fights and monster encounters could you really get through without losing a leg at some point?
EDIT: actually, 20 headbutts per second (120 per round) wouldn’t be a bad attack at all, especially if paired with a spiked helmet or something, geez

Encounter: unusually friendly mummy created using an experimental process that left its usual spiced odor replaced with a sugary orange-cream that wafts and lingers, including on any creatures that it infects with Mummy-Rot. It can also summon similarly-scented Will-o’-Wisps and size-small Gray Oozes, both of them tinged unearthly shades of orange, pink, and red.

Item: Bear-Tooth-Holding-a-Shark-Tooth Necklace, doubles the damage delivered by bite attacks

Encounter: Lööp Mërchänte (submitted by @achybaton)

Item: Ward Uke, a translucent green ukulele that allows the player to cast Guards & Wards. Players are cautioned against using them in any realms in which they may run up on any of the Iconic Characters of Greyhawk, because War Duke hates these
Item: hunk of elemental sodium, made into the shape of a duck for absolutely no good reason. Explodes on contact with water.
Credit: found by @lovecoresockhead who is probably super tired of the original version of this post, even if I did rearrange it to fit better on dashes







