It's funny that I actually remember mine all these years later, but tell me, former/current D&D playmates, what was your worst fail roll you remember doing?
Mine was killing another player with an errant arrow. I let fly a short-bow arrow while we were fighting some kind of creature in a densely wooded area, so long-range weapons were a challenge. I remember I didn't have any magic left, so when my turn came, I asked if I could somehow get within 50 feet of the monster(s). I was told, yes, I could, so I rolled to attack with a short bow. Well, it came up a 1, and the DM glanced at his notes. My arrow bounced off two trees and sailed back towards us, causing everyone to duck and lose a turn - except one unfortunate man who was weak on HP to begin with, and was trying to rest against a tree.
My arrow took him right in the chest for 10 HP and he died.
Ooopsie. ?
Iunno if everyone would call it a "fail" roll...
but my group got ambushed by a giant wurm-thingy, cuz we faileded our 'perception' stuffs. It popped up right in front of me and I hit it wit my sword.
Then it went... and it swalloweded me.
Teh others all almost died savin me from dat one too, but managed to kill it, and it fell on one of dem (knocking his ass out) befire i came tumblin out of its mouth, sword in hand (for a lil bit), and ended up stabbin teh knockeded out chara wit it and killed him by mistake cuz I was mid-attack when it all happened, and got a crit on the attack, but faileded balance.
It was funnier at teh table...
My fox-girl thief tumblin out of its mouth, her sword goin flyin up in the air as it slipped from her grip, dm randomly determinin the square it landed in, and resolving it as an attack on that square... which i crit on wit a nat-20.
So... fail-roll... or crit-hit roll?
I call it a fail, cuz i wasn't tryin ta hit that player's chara... I wanted ta hit the wurm cuz it tried ta eat me in a very not-fun way >,.,<
My group has/had lotsa crazy shennanigan-stories...
Some good... others not-so-much.