Craziest Thing That’s Happened to a Party/the Characters/the Players
The time a character used the last ring in a ring of three wishes to escape a sticky situation, then worded the wish: “Get me the hell out of here! No, wait!”
The dungeon so ridiculously deadly that the DM didn’t bother giving the NPC hirelings names; he just gave them numbers.
The time we played “Steading of the Hill Giant Chief” with 4th-level characters. Because how hard could it be, right?
The time a PC was badly dismembered in a flooding temple that the rest of the characters had to desperately escape. But needing to grab all of his body parts for raise dead, they opened up a bag of holding under the water and vacuumed up a sanguine cocktail of his watery remains. When they later opened the bag to pour hi out at the temple, it wasn’t pretty.
The time an eight-armed stone golem armed with scimitars of sharpness hacked apart an NPC cleric who had gone temporarily insane and tried to desecrate an area of the dungeon that the golem was guarding. Only the cleric was wearing a ring of regeneration, so after the golem dismembered him, he’d start to come back to life again. So the golem would hack apart his still-regenerating remains once more, and the cleric would start to come back again, so the golem would hack apart the even more finely diced remains again, and so on. This went on until there was nothing left of the cleric but a fine paste.
The time a troll was wearing a ring of fire resistance that the PCs never bothered to search its body for after they killed it and set it on fire for good measure. So even after burning, enough troll-stuff was left clinging to the ring that the troll eventually regenerated from it, and went off in pursuit of the party. Whereupon they killed and burned it again, once more not bothering to search it for rings. Whereupon it would regenerate again and come looking for them, even more ticked off about having been killed each previous time. This went on for about a week before they figured it out.