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Way back in 1e, a friend started a campaign where we got teleported to a desert island and had to find our way back. We woke up on a beach, and could see a small city off to the south of us, some impassable-looking mountains to the west, ocean to the east, and beach curving off to the north. We decided to head south to the city to find out where we were, which wasn't the way we were 'supposed' to go. So the DM had a huge sand-monster rise up to chase us north. My fighter, on his heavy warhorse, charged it with his lance. Now, back then, weapon damage was based on the size of the monster you hit, and a lance did 3d6 against large. Double damage from the charge, doubled again for the crit...and I rolled a 16. 64 points of damage in literally the first die roll of the campaign. Killed the monster outright, and the DM, somewhat stunned, announced that I'd just ruined his campaign because we were supposed to go north round the island. He got up and left. We never played any farther in that campaign.

Geistlinger |

The most incredible display of critical hits I've seen just happened today in our DnD 3.5 game. It wasn't so much one critical that did a lot of damage though...
The Chameleon cast an Empowered Storm of 10000 Knives on the leader of the group of bards who were attempting to capture the party and sell them into slavery.
He threw 48 daggers at the bard leader, hitting with 20 of them, 9 of which were critical hits. The bard was dropped to -6 HP, with ability damage to 4 of his 6 ability scores (1 pt to each Str, Dex, Cha, 3 pts to Con), reduced to 1/4 of his normal movement rate, and a 3d6+1 Bleed. Had his compatriot not cast a Cure Serious Wounds spell on his next turn, the leader would undoubtedly have bled to death on the Chameleon's next turn.

Selgard |

It was my very first game of my very first PFS character ever.
A level 1 human Oracle of Life, wielding a heavy mace.
We snuck up to some guys, but they spotted us before we could pull off the ambush but some of them still had to climb up to get us.
3rd round into the fight, one guy managed to get up close to me. I had a very low AC and my offense was negligible. He took a swing. he missed.
I took a swing. hit, crit, dead.
Doesn't sound like much, but it was worth a pretty good laugh at the table. took the guy 3 rounds to get to one of us, just to get a mace to the face :)
-S

voska66 |

Last game I was playing an Anti-Paladin at 8th level using a Falcata. The wizard in group put haste on the party. So I had 3 attacks and engaged a Paladin who was level 10. The paladin used smite and moved in to attack with a standard action and missed. I retaliated with 3 attacks with smite good and power attack and fiendish boon unholy. I rolled 19,19,19 for the attacks and confirmed all three criticals. So I did 3D8+66+2D6 per attack rolling 25, 27. 20 for damage doing a grand total of 250 damage in one round. Exceeding the paladin's hit points by just over double.

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My best crits have been with my crossbow-wielding ranger. Most recently, he took out one of his best Favored Enemies (Aberrations) with a shot worth 100+ points of damage at level 15.
Several levels earlier (around 10th or so, I think), it was 80-something points of damage to the iron golem-generating "orb."
Ranged criticals are somehow extra satisfying and I don't know why.

Orange D20 of Death |

Holy cow! Thanks for all the posts! Nice group of fine people here. :D
I just scanned over a few of the posts, saying there are over 50! I will read them all, but I was just about to play some Dungeon Delve at the moment and will get back to reading them. I did see a few questions, namely about the creature killed. It was a Vrock out of uggggghhhh.. I cant recall the number, but Pathfinders Second Darkness series. Oh and it had 6 mirror images! The luck was with me on that... mighty, MIGHTY swing!

NobodysHome |

Not exactly a proud moment of my life, but I'd *finally* convinced my girlfriend to play Runequest with us. She spent several hours rolling up her character, coming up with a good name and background story, carefully choosing her equipment, etc., etc., etc.
We entered our first combat, and I drew back my bow and fumbled. As the very first shot of the very first combat. "Critical hit nearest friend." Her mini was right in front of mine. I rolled location -- another 20! The head. And I rolled max possible damage. Put an arrow through her head and killed her instantly.
It was MONTHS before she would game with us again. (My friends hadn't helped in the least by rolling around on the floor laughing the entire time).
To my utter astonishment, she's still with me 25 years later, so I figure I'm at least doing something right.
And, since this is a PF thread, the most "epic critical" we've had was from (of course) a paladin with Smite Evil going. Our house rules on crits are that you get to keep rolling until you roll out of crit range.
So he fired his bonded Holy composite longbow with Smite Evil going at an orc sentry. 20. 20 (x3). 20 (x6). 20 (x9). 17 (x12). 12d8 + 12 (+1 weapon) + 36 (+3 STR) + 144 (Smite) + 2d6 (Holy) = 237 points to the orc. Yes. A plain old, everyday, run-of-the-mill, orc. Surprisingly, it didn't survive.

SmiloDan RPG Superstar 2012 Top 32 |

In 2nd Edition, we houseruled that if you rolled maximum damage, you got to roll again. Well, after a battle, my tabaxi (jaguar/leopard-folk) monk/kensai went to drink a potion, and found out it was missing. So, he grabbed the halfling thief around the throat and lifted him up, rattling his brain-box so he would give me my potion back. Instead, he gave me the pointy end of his dagger, and rolled, 4, 4, 4, 4, 4, 4, 4, 4, 4, 4!!!!!! So many 4s!!!!!
So many 4s, in fact, that my character died! :-(

Interzone |

...
As the rogue's rapier drove home to the hilt, punctured the dragon's heart, and flooded its system with icy cold, it cried out in angry defiance before freezing solid.Where the entire party fled, only the cohort stayed behind to one shot the menacing wyrm.
That is so freaking awesome.

BlueAria |

A friend once "crit" an ancient blue vampire with sunbeam (or what ever spell that insta gibs vampires if they fail the save) the dc was something like 25 the dragons reflex was something like +40 but it rolled a nat one. everyone one in the party got dominated the round prior and we were all screaming at him to cast wish to undo the dominate but no he insisted... i guess he made the right call

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Not epicly high damage, but was pretty awesome.
I was the gm, and the party was at a tavern, trading insults with a noblesman adventuring party. The party's half-orc barbarian had had enough of the other group, who had turned their backs to walk away, so he declared he would walk up to one of them (rogue), turn him around a plant a fist in his face.
Well, I ruled a perception check, followed by initiative, the rogue succeed and beat the barbarian, turned around as the half-orc was approaching, grabbed the nearest object (a mug on a nearby table), threw it and rolled a crit. Using the Crit Deck (GameMastery), I drew a card saying Throat Hit; Target is Fatigued for 1d4 rounds...
I think the damage was around 12 points, so not overly impressive compared, but the players were flat on their backs laughing.

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In 3.5, Eberron.
One PC is a Paladin/Monk with Whirling Steel Strike (allowing him to flurry with longswords) and the normal "flurry of misses" that such a character will be expected to throw.
It got so bad, in fact, that he started carrying around some 12-20 longswords, all strapped in "quick draw" sheaths (think hatchet loops or carabiner straps) and chucked them at foes.
Then, along came a mounted patrol. Moving at the party in classic "Cowboys vs. Indians" motif, the group is more or less stuck in place while the horsemen charge, wheel, and pepper them with arrows.
The leader of the horse-folk charges the Pally/Monk, who readies a single attack to the tune of "I'm gonna jump up and chop his head off" or somesuch flavor text.
Wouldn't you know it, he rolls a 20/20/20 (house rule we used to have, 3x nat 20 = instant kill) and off goes his head.
The rest of the horse people turn tail and flee, once he pulls off his "Nameless" trick.

toastwolf |

while have I have never had one of these awesome moments i recall a session of 3.5 when during the starting turns of a rather large barfight
one of my friends managed to double 20 coup de grace from a sitting position with his battle ax... as an AOO, didnt even bother puting down his beer and getting up for the remainder of the fight (mainly cause the npcs steered way clear after that spectacle)