I was using my first-ever character, a Half-Orc Barbarian named “Sam-R-I” and also nicknamed “Cuddles”. Anyways, my most funny/improbably moment came when the party faced a room with a treasure chest.
The room was loaded with traps, as the PC who stepped on spike-trapped floor found out (I believe it was our ranger). There were also lots of suspiciously arrow-sized holes in the wall a few inches from the floor.
My character, being obsessive about personal hygiene had bought several bars of soap while we were in town. So I slid a bar of soap on the floor towards the treasure chest on my turn. The soap activated the arrow traps on the floor panels, and ended up being pierced several times.
Thankfully, the arrow traps were just a one time thing, and my party was able to get to the chest and recover the treasure within.
Another fun DnD moment (later in that campaign) I went into a room to get some treasure. The druid was near the entrance, and the wizard and ranger were 5 or 6 squares from the druid. I went to open the chest, which had a LOT of gold (30000 gp!). However as soon as I took the gold, a stone door slammed down where the entrance was, trapping me in the room.
And water started filling the room.
The wizard and ranger were unable to do anything, and the druid was stumped. About 3 rounds later, and after a few Swim checks (good thing the dice favored me, I had half-plate on at the time. The druid decided to use “Soften Earth and Stone” on the door, which quickly became mud. The room was full of water, so the other party members got hit with a surge of water and mud. The druid got hit by the mud, the water, and my Half-Orc Barbarian. I’m glad she didn’t die.