Context: My tortle barbarian (Yog) rolled Nat20s 4 out 5 times when trying to throw our halfing like a ball.
Cleric : Yog why are you so good at throwing hafling?
Yog : its our national sport. I was gold medalist 3 years in a row.
(once the party stopped laughing)
Dm : you know what? add it to your proficiency.
Yog (ooc) halfing throwing? For real?
Dm : yes. For real
Me, ooc, after we had defeated The enemies in one room: “Can I roll to summon Billy Mays?”
Dm: “wha-? Know what? Sure. If you roll a 20 you’ll summon the ghost of billy mays.”
I roll a nat 1, and everyone else rolls to summon him because we apparently really wanted to summon him, and finally our fighter rolls a nat 20.
Dm, sounding defeated: “you manage to summon billy mays.” He then does his best billy mays impression and goes “HI ITS BILLY MAYS HERE!”
Our fighter: “can I absorb his soul to gain his powers?”
Dm: “fINE”
A mimic that consistently chooses contextually inappropriate treasure containers to impersonate, like a filing cabinet in elven ruins or a stone sarcophagus in the storage room of the local inn.
An abnormally intelligent undead skeleton that indicates through elaborate pantomime that it wishes the party to sign a petition demanding better working conditions for its bony brethren. It’s unclear who – if anyone – the petition’s intended recipient is.
A giant spider peddling fine leather jackets that it fashions from the hollowed-out skins of its prey. The player characters can be either customers or raw material – it cares not which.
A gelatinous cube whose exceptionally precise dimensions have won the favour of the gods of Order, granting it both awareness and the power of speech. The endless hunger of its kind has become an obsession with sharing its perfection of form with the world: all shall be cubed!
A horde of tiny, gremlin-like demons that secretly improve mechanical devices rather than sabotaging them. Their idea of “improvement” is peculiar, typically involving making the device in question go faster.