Best things done on the roll of a one.

[novyet]

The weirdest one I've had recently was, a rogue I was playing, came up to a cliff's edge and did a running jump to make it to the other side, it's not a real long jump so I go for it. Of course I roll a 1, and plummet down to the bottom of the cliff, which does a ton of damage and nearly kills me, but thanks to my amulet of health I come through just barely, but since it did over 50 damage, I make the mass damage save, and get another 1. Which of course means I'm dead, but out of spite, my dm decides to check for breakage of any items, so we randomly determine it's my alchemist's fire. So when the rest of the party comes down to find me, they of course find my mangled flaming corpse. And they still won't let me forget it!

 

[Plane Sailing]

A rogue in my campaign, on his last legs, decided to Use Magic Device with a wand of shocking(grasp) on the foe. Rolled a 1. I ruled that he was holding it the wrong way around and zapped himself.

Harsh but fair, I like to think

 

[MeepoTheMighty]

I was running a party through the Sunless Citadel and the party had reached the goblin chief's lair with the vine-covered shaft leading down to the second level. The party wizard (a new player) went to climb down and rolled a 1 on his DC 5 climb check.

Okay, roll again to see if you can catch a vine.

1.

Roll one more time.

1

Okay...er...(desperately trying to not kill a first-time player) roll a tumble check to see if you can avoid some of the damage.

1

That die hasn't been rolled since.