So, I feel this needs to be brought back from the old forum. As I edit last years campaign games I ran for the community AP Site especially (I have found some gems). Please feel free to share those outrageous moments brought on by the roll of a die.
I'll start it off.
So in my Monster of the Week Zombie Continent campaign. The crew had split up to investigate goings on in an eccentric survivor town. The guy with the lowest intelligence and most absurdist actions (the "That Guy" of the group) went his own way to break and enter into an art gallery of an Occult Artist held at the local hotel. The other guys went to investigate the Artist's Manor on the hill.
Crash (That Guy) pulled off a perfect stealth mission into the hotel and collected vital clues on the mystery. (Seriously he rolled the best he'd done thus far)
Kramer-O, Niles, and Jitterbug (the other characters who have been a bit more serious on dealing with things than Crash) encounter a set of Zombies in the kitchen of the Manor and Kramer-O proceeds to grab a sandwich made by the Manors residents prior and pulls his gun out... (makes his rolls)... and proceeds to bite down on the gun and "shoot" his sandwich at the Zombie... But hey, he got some Frank's Red Hot in the zombies eye socket?
The following rounds resulted in consecutive failures and 3 stooges gags to try and escape the Manor, because they just couldn't kill these zombies.
I believe Cramer-O's last words as he ran from the Manor was "THIS PLACE IS CURSED! HOLY F@$&!!! RUN! GAME OVER MAN! GAME OVER!!!"
It was a beautiful roll of the die.