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One of the parties I was in was investigating a crime and came across a victim who wasn't quite dead yet but would die quickly without medical attention, so the cleric rushes forward and wanting to conserve spells (we were level 1 and the game had just started) rolls a heal check, gets a 1, and instead of healing the guy breaks his neck.

In another campaign under the same DM our party's barbarian found a way out of the sewers we were in...an old rusty staircase. However, the barbarian failed the spot check, and blinded by the light coming in through the crack of the manhole cover, starts climbing said stairs. She made it to the top, only to have her hands stuck in webs set up by the giant spiders that were living in that room. Kicking and flailing to break out, she struck the stairs, which collapsed so that the rest of the party couldn't help her.
Just last week I rolled a natural 1 on a jump check.

My damn rogue fell to his (almost) death. It was BRUTAL, I'll tell you, I really almost didn't make it out of that dungeon alive.
This one time, I was playing a bard trying to fight in melee combat. I rolled a natural 1 which caused me to accidentally let go of my sword and have it stab and kill a friendly NPC. sad
So I'm DMing this campaign where an npc was spying on the party while his buddies attacked them. The party kills his buddies and is about to move on when I roll a 1 for his move silently as he tries to get a better view. The players quickly throw the halfling monk up on the building where they heard him. Seeing the monk, the npc decides to make a run for it. He runs to the other side of the building and jumps. I roll another 1, so he breaks his legs on the landing. For some reason the party barbarian decides to try and help him. He makes heal checks to bandage the npc's broken legs, both rolls are 1 or close to it. Now this poor npc will never walk again. To top it off, the barbarian decides he can't just leave him there, so he disarms the npc and straps him to his back. Now this guy is being carried around helpless in the dungeon he was trying to keep the players out of.
My lvl 1 half-Orc monk was attacking a goblin and I had been getting quite a few misses, so out of frustration I declared that I was going to kick the goblin in his wrinkly yellow balls. So I roll a natural 1 and proceed to kick myself in the balls, losing a round in the process.
Alright so since SciFi club (basically D&D in disguise) was canceled to save any luck I still had with my dice occasionally I would take them out and roll a D20 to see where I wanted to go with a rp. So my little 14 year old character, a lanky, malnourished Brit boy is going against this total ***** Frenchie lizard guy wants to...errr...do some bad stuff with him. So somehow I got the lizard-man under truth serum and while he's influenced and nearly spilling out the answers he needs there's narrated how a dark shadow is right behind him. So I got the perfect idea: "Hey, I'll use my D20 to see how hard I kick their arses!" I rolled a 1. Good things did not happen. I am still raging.
Apotheosic's avatar
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we get surrounded by evil monkeys and the party scout pulls out her fancy new magic rapier and goes to attack. rolls a 1. her fancy rapier shatters into tiny little pieces. ha.
and one time i choked myself with my own quiver. the timing couldnt have been worse either, as a small horde of zombies was approaching fast.
and another time our cxleric stabbed herslef in the leg. she'll never live it down.
xEmeraldPhoenix's avatar
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I once rolled a 1 trying to jump a 5ft across hole in D&D as a Druid and fell down 50 ft to -9 hp. If it werent for my Young Bronze Dragon I would have died...FROM A HOLE!!!!

also my Cleric rolled a 1 on a heal check in LFR, killing the enemy that we needed to question...

and my Rogue once rolled a 1 on a move silently on the deck of a ship and broke the loose floor board causing her to get a huge splinter causing 2 damage and alerting the guards to her location, but she had a 34 on hide so she was ok.
In a D&D campaign, our party was beset upon by a band of orcs as we were at camp. Naturally, we were ill-prepared and caught by surprise, but quickly grabbed our gear and got into the fight. Notable is that, in the previous session, we all gained minor magical weapons from an evil warlord's cache.

What follows happened in one round.

The first fighter, a ranger-esque kind of guy, attacks an orc. He rolls a 1. The DM, giddy at the chance to inflict some serious hurtin' on us, rolls on his special "critical fumble" table. The result came up as an 8 on 2d4 - a successful double damage hit, but the weapon breaks. That's when a team member pointed out that a magical weapon *technically* can't break... so the GM sighed, and said, yeah, go ahead... double damage, but you'll be flat-footed for a round thanks to the sheer impact of the blow.

So then I went, the fighter. I rolled to attack... and rolled a 1. The GM chuckled a little, and rolled his 2d4 chart... and got another 8. He sighed, and told me to roll for damage... same effect.

Then the last player, the cleric, took up his d20, and rolled. You guessed it... also a 1. The DM picked up his d4s, and rolled them, then just kind of stared at the table behind his GM shield quietly. The cleric said, "What, did it come up as an 8 again?"

The GM's reply: "JUST ROLL THE [censored] DAMAGE."

What were the odds of that precise sequence happening? Basically:

1/20 x 1/20 x 1/20 x 1/16 x 1/16 x 1/16 = 1 out of 32,768,000.
In one round, I did something with a 1/320,000,000 chance, by myself.

I was a level 5 ranger, and at the start of that session we were attacked by bandits during the night. Our Bard who is wielding the enchanted sword we are supposed to be returning is on watch. Well as one of the bandits start slicing into the tent, he wakes my ranger and casts glitter dust out the slice in the tent, my tent by the way. My character, was our damage dealer, you don't want to know about our tank. I had made it so he duel wielded b*****d swords, and had some nice mithral chain. My animal companion is still asleep though. Well I get up and draw my swords while getting ready to fight person outside the tent. I failed on my spot check to notice the halfling bandit leader walk in the entrance of the tent, and coup de grace my animal companion. Poor wolfy went down to -9 hp.So I jump over wolfy, and crit the leader twice, slaughtering him, while the other 4 bandits are coming in through the tent walls.

Next round, while yelling at the druid to heal my wolf, I go to attack the bandit blinded by the glitterdust, through the tent. I roll a 1, so the DM tells be to roll to see if I fumble, I roll another 1, he tells me to roll a luck die and I roll another 1, he then tells be to roll a d%, I roll a 00, and he tells be afterward it required a 23 or under to pass. So then he tells me to roll an attack with the other hand, nat 20, and nat 20 to confirm crit. I'm thankful for healers, because the dm said i made to grab my hand as my +3 defending b*****d sword stuck in the tent, saying my char was forgetting that I had a b*****d in my other hand. So I crit my wrist for 24 damage with my +1 b*****d sword in the other hand.

I later stopped using my dice, and used the person's next to me cause I didn't like the rolls i was getting with that due to 1's and crits.
Designer Genes's avatar
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I don't believe in punishing players for something that happens about 5% of the time (about >1% the time if double one rules i used, which over the course of a capmaign, is actually pretty likely), and is already bad (missing automatically.)
Missing the story of Grok, the half-orc barbarian.

Known for his complete and utter lack of tact, and yet also his tactical brilliance. And the fact he favored a large, vorpal two-handed sword. His pride and joy, that sword. Used to slay many villains over the course of that campaign, and a few people that were just slogging down the whole 'stop the evil overlord' business with bureaucratic red-tape. ("I think I have a solution to this issue." "And that i-" "*ONESHOT.* Anyone got a problem with that?" "...nope. Not a one." )

So it comes to pass that, against one of the lieutenants of the evil overlord in question.. on a rain-slick castle wall, during a magically conjured thunderstorm, that Grok ended up beheading himself due to a series of unfortunate events (he tripped on the cleric, and thanks to the rain and blood already covering him, lost his grip... Crit Failure on the hit, Crit confirmation on hitting myself. With a vorpal sword, no less!). Thankfully, the rest of the party was able to continue the fight on, bravely (the rogue capitalizing on the fact everyone ELSE was busy being torn between laughter and shock), and Grok was later resurrected and informed of just what happened.

The rest of that campaign, he used a warhammer. And I've avoided vorpal or vorpal-alike weapons ever since!

(The DM checked to make sure it was alright I one-shot myself, and I found the entire thing freakin' hilarious so I decided to roll with it. Both puns intended.)
Apotheosic's avatar
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we have finally reached the heart of the mysterious unexplored jungle island, and are confronted by a very menacing undead mastermind (i think he's a necropolotin or something...) and he summons up hordes of undead to destroy us. there is a convenient hatch in the middle of the courtyard that we can escape down after a few rounds of prying it open as the hordes shamble closer. just to be dramatic, our cleric decides to turn undead on his way down. after a dramatic speech, he makes the roll. natural 1.
the whole room died laughing.
not really a critical failure story but still funny, and involves lots of failing.
So we're clearing out a cave full of enemies. me (as a rogue) and my friend as a paladin, both females. our paladin finds some better armor, so we deiced to stop so she could put on her new armor, so as she starts to undress, the DM decides it would be a good time to have enemies attack. so here's our paladin wearing no armor and topless, and my rogue surrounded by kobolds. first round I go first, and roll a 1, causing me to drop the bolt I was trying to load into my crossbow. so I was like as a joke the paladins tits are distracting me =x
next round I roll a 2 and was like... I swear its her tits they're all bouncing and distracting me....
next round I roll another 2 and everyone was like ok your char is clearly a lesbian and loves the paladins breasts. I was just like /sigh =x soo what if I do?
next round I move behind a wall to were I have no line of site to our topless paladin and roll nothing but 18-20 for the rest of combat.
needless to say for the rest of the game, not just that session but all sessions after that. noone let me live that down, and it actually became part of the story lol my rogue always saying innuendos and trying to hit on, see our paladin naked again lol....
A friend of mine was playing the Zerth Cenobite (sp), he missed on an attack roll from a fence poll, and used the ability to "travel back in time a moment and re-attack"... rolled a 1 so the DM made it so the timeline changed, placing a slice of cantaloupe on the poll, he slipped and fell off in front of the orc he was attacking lol

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