Item: Dorkometer, allowing the wielder to measure the Dorkosity of a subject, as well as to indicate the direction of dorky creatures or objects.
Encounter: an unusually glamorous and fashionable manifestation of the party’s guilt for past killings
Item: a potion brewed from wild fruits and dew harvested from the mountains by drow, granting +3 on any Skill Checks (Gaming)
Encounter: Dead Drummer; can influence the walking/running speed of the party by the tempo of the beat he drops on his ethereal drum. Also, glowing eyes.
Item: Socks of Bitcoin Farming; once per day while worn and connected to WiFi, they use the energy of your body heat and tread to add one bitcoin to your account.
Encounter: grumpy old Dad of the Harpies. Assumably he grips the sword in one of his feet, but since Harpies can’t fly, it’s not really clear exactly what he can do with it. Maybe the sword is a Dancing one?
Item: All-Terrain Atmospheric Armor #3, +10 against all types of environmental damage; also provides an air supply of 8 hours with proof against any kind of poison gas attack. -10 on Agility checks.
Encounter: goofy bat-thing with the power to raise the dead, which it does at every opportunity for its own amusement
Item: gun with, like, a LOT of bullets
Encounter: there has to be a more interesting name for these than “Star-Creatures” but
Random Item Drop 