D&D game. The concept was an Adventurer's Guild. So we each had multiple characters and we'd take turns DMing.
My favorite character was my Drunken Monk.
Now, for a bit of backstory: we had a houserule that if you rolled a nat20 on attack, you rolled again. If it was another nat20, you instakilled your foe. Why? Because why not.
Anyway. So my drunken monk was off on an adventure with his guildmates. We end up in a cave an holyshitdirecavebear. So my turn comes up:
"You mentioned an underground lake. Does it have any of those blind cave fish in it?"
DM: "Uh, yeah?"
"Alright. I'm going to catch one."
DM: "Ookay."
So I did.
My next turn comes up (meanwhile, the party is floundering against this thing already).
"I attack the bear with the fish."
Everyone's just sort of facepalm, but hey. Drunken monk. Improvised weapons. I gave no shits I only roll a d4 on damage for them. I WAS ATTACKING A BEAR WITH A FISH.
Nat 20.
DM: "...roll it again."
19.
The DM decided it was just too ridiculous not to: "...You impale the bear through the eye. With the fish."
To this day, one of my most glorious D&D moments.