D&D Players, What's your luckiest dice roll?

What's your luckiest dice roll?
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[@OmegaBigRed]

The party opened a door to a room that had a sleeping ogre. Druid turned into a giant spider to sneak across the ceiling. Nat 1 caused druid to fall and land next to ogre, who proceeded to keep sleeping due to his Nat 1 for Perception. After that, everyone managed to quietly walk trough the room, including the Loxodon.

[@LordUrfael]

Why did the druid have to roll anything to not fall?

[@lt32p1]

​@@LordUrfaelHe rolled for stealth. Nat 1 had him fall

[@-.CosmicCode.-]

I rolled to persuade the sky. I hit a nat 20 and spawned a meteor

[@tudodaretro]

guess I'll die

[@lonkelly1878]

Had a kitsune rogue in a modern setting pull up to a social event in an Aston Martin, when asked if I was on the list I said I wanted to imitate James Bond. Rolled a 7 on a d100, in other words 007. DM gave it to me after we stopped laughing.

[@SuperZez]

The story took us to an archaeological dig in a homebrew setting where kobolds and goblins were extinct. The artificer and I rolled *simultaneous nat 20s* when we all joined in the dig, and we discovered a 3000-year-old perfectly-preserved kobold corpse that the archaeologist on site called the discovery of the century.

[@rhodes3983]

Nat 20 on a death save immediately followed by a sneak attack critical

[@SnowySabreToothedLeopard]

I was playing in a D&D campaign, and I was playing a then Battlemaster Fighter 5/Paladin 1 Multiclass, and we were in a dungeon fighting a band of Yuan-ti and their acompaning band of lizardfolk and kobolds. We were taking a short rest in a cave with a river adjacent to the walkway before the final section of the dungeon. Prior to this, the enemies were drinking a random assortment of potions to gain some temporary effects for the fight, and we began drinking them ourselves to see what we would get. I drank my potion and had to roll a d10 to see which effect I got. I rolled a 10, which granted me the enlarge spell that lasted for 10 minutes, but because this was in downtime, I decided to make use of this skill by fishing in the river using my magical fishing rod. How the fishing rod works is that I made an athletic still check at advantage to catch a fish. With this magical rod is that I could use an action to cast my hook into a different plane of existence to the one I am in and get some cool exotic fish as either pets or as food which grant me special percs. To determine the rarity of the fish, I roll a d100 to calculate the rarity and go from there. So I make my roll at advantage and add my d4 to my athletic still check and get a nat 20 + 4 from the d4. My athletics modifier was a +6, making the total a 30. From there, I rolled my d100 and got... 100. My DM took a look at his notes and went silent as I thought of what odd or exotic creature I could get as a pet. What I did not expect was needing to make another d20 Athletics check to prevent me from being pulled into the hole in reality forming. I made my Athletics check, this time a regular roll, and got another Nat 20, this time with a total of 28. Managing to avoid the grapple, I pull out an entire BABY KRAKEN!!! And upon relising this, it told me in primordial that it would let me live if I vowed to never tell anyone of what happened and never chose to seek it out again. The kraken then made its way up the river and through a waterfall and was never seen again.

[@jakefrost7404]

*_Aggroed a Lich (CR 22, we were later told) in its sarcophagus, located in the cargo hold of a ship that was transporting us to the next continent. Our party was level 3, four members strong, and with no healers or serious casters, an obvious party wipe. Both of our frontliners were monks._* *_Monk 1 managed to strike first with a Nat 20, and instead of rolling for critical damage, Monk 1 chose to trip it and knock it prone. DM was a good sport and rolled for Severity, a Nat 1 on a d100, the worst outcome for the Lich, making it not only fall prone but busting its skull pretty badly on something on the way down, stunning it. Monk 2 followed up with a magic bag that he recently discovered was a Bag of Devouring. He black-bagged the Lich head-first._* *_Since the Lich was stunned, that meant no Legendary Resistances or any other actions. The DM could only watch, helplessly, as one of his campaign's biggest bads was slurped up into the Bag of Devouring and destroyed. We then searched for, found, and destroyed the phylacteries it had hidden on the ship in short order._* *_The DM was, understandably, much less charitable with us from then on._*

[@CrazyHawkeComics]

One time recently my dragonborn barbarian had to make a Dex. AND Str. check in a row to rescue a love interest from a trap... Nat20 twice in a row!

[@Spoofopolis]

One of my friends joined the Pathfinder game I was playing with some of my other friends. On his first roll he said "nat 20 let's go" and then rolled a nat 20. He consistently rolls nat 20s throughout all the sessions we've had since, like way more than normal. I'd accuse him of using weighted dice but we roll on Foundry lol

[@codyscott999]

My old players rolls. I was DMing for a new group that I had home brewed a mix of 3.5 and 5e for. If they were on critical health or during a "story" moment, I'd roll openly. The number of ones I saw was both disheartening and hysterical.

[@gamehero6816]

Almost every roll in a DnD session, assuming the rolls in question had to do with a secret library and a lore-related book we stole from said library.

[@lobesteriiiesq3772]

We were helping save a village that was under attack by cultists at level 1. I was using a homebrew class that mostly just lets my fists do 1d8, so I don't need a weapon. The lowest roll I got that session was a 17. On one of my (many) nat 20s, I punched a guy so hard that he flew into another guy, then both of them flew into a nearby burning building which promptly collapsed on top of them

[@postapocalypticnewsradio]

PANR has tuned in.

[@LarryJ2022]

When we do random encounters in one of the campaigns I'm in, the DM will pick up a d100 and ask high or low. Without even thinking I just said 87. And that was exactly what was rolled. We ended up encountering a traveling merchant that sold some nice things.

[@Xarestrill]

This happened a couple of days ago. I'm running a Forgotten Realms campaign, and the party was taking a break between adventures to do some roleplaying stuff. One of their home towns was fairly near, so they traveled to visit family and returned just in time for Highharvestide (kind of a cross between thanksgiving and halloween with lots of contests of strength and dexterity (and food related ones too). The party took part in a bunch of the contests as befitted their skills and interests. One of them, a rather reserved individual (an immortal who doesn't want to care about others because he'll outlive them and doesn't want the pain of their deaths. A big part of his story arc is coming to care for the rest of the party almost against his will) decided on a whim to take part in the catch the greased pig challenge. It was basically a series of dex checks for everyone involved where someone had to out roll everyone else (and the pig) for 3 rounds in a row to win. I was rolling for 8 npcs and the pig. Most of the rolls were pretty average, some high, some low, a bunch in between, but on one roll 6 of the 9 dice came up natural 20.

[@zinmaster24]

When I rolled high enough and correctly guessed a coin flip to not die by getting sucked into the void dimension where the evil gods reside. This happened because I put the Necrocomicon inside of a bag of devouring. It was great. But I ended up creating the fourth horseman of the apocalypse. 😂

[@ReinaSaurus]

3d6 turning into an 18. the monk needed the highest modificator to make a jump test through very dangerous terrain while being shot at and by failing he would not only not reach his opponent, but also take serious damage by falling combined with sharp metal scraps and stone spikes, while a 1 on any of the rolls would mean death. he reached a group of five archers and made quick work out of them in melee. during the rest of the encounter the party got completely and utterly obliterated though.

[@rhysbyrne5996]

I rolled a nat twenty counterspell save after the big bad counterspelled my counterspell of its disintegration we were level 6-7

[@shanepatrick6836]

Had lucky Nat 1 followed a Luck Nat 20. Due to some shenanigans with a magical item, I teleported my self to several spots across the city until I found myself in the party’s favorite tavern. I decided to wait for them since my party seems to have “substance abuse” as a requirement for joining and figure they’ll pop in for a few rounds to celebrate freeing a bunch of slaves from some slavers. While I’m pregaming our Bard pisses off one of the slaves who turns out our DM intended to be an end game villain (we’re level 4 at the time). We all roll initiative and to keep me sane since even knowing my party was now fleeing a huge sized devil was metagaming, I set to describe what my character is doing while waiting (almost always the most mundane and calm things to make a kinda comedic juxtaposition to the possible fight and retreat the table had on their hands.). At one point my character grabs a newspaper and opens to the crosswords. DM has me roll an investigation check to see how I did. Nat 1! I supply the DM with the response ( He reads the first clue “1. Down: A four letter word for fornication starting with the letter ‘F’” and thinks “Well, I got nothing!”). The table laughed. On my next turn, I continue the joke from the previous turn and in frustration with my crossword skills, my character takes the sheet, folds it into a paper airplane and tosses it out the window of the highest level of the balcony of the tavern. DM asks for a sleight of hand check. Natural 20! The only one of the entire session so far. DM asks me to Roll 3d4 (I total 11) and describes the paper airplane soaring above the streets and out of sight… and asks me if that was my turn. Confused I end my turn and the Devil’s turn begins. DM describes the Devil stand ready to launch his attack and begin a monologue about how the party were mere insects before him, and nothing would stop his conquest of the wor- only for an errant paper airplane to come down from on high and collide at high speed right in the devils right eye, piercing it for the 3d4 plus twice my sneak attack damage. Which the party used to escape. And that, Ladies and Gentlemen, is why my Rogue’s most prized weapon on his character sheet is “The Paper Airplane of Fiendish Eye Gouging.”

[@umecoalpaw7573]

7:36 damn, that's some Anime ah bs that happened XD

[@aidanjackson5084]

A few days ago we had Hollow Knight's Greenpath music as video background. Now we have Zelda: Skyward Sword academy(?) music as video background Really enjoy the Video Game OST selections in video backgrounds. Very enjoyable

[@darkphoenix539]

Sneaked through enemy outpost, heavily guarded, with team of two paladins, cleric and drunken, mumbling druid.

[@ZombieDish]

We were facing a Earth Elemental and my Bard had Shatter. It got cast. I rolled two 20s, and the DM rolled two 1a and the DM was like. Well I guess it's dead now.

[@lordpyromis5109]

ok so this one is a long one but its by far my favorite so I was playing a Eladrin Arcane Trickster Rogue named Eltair Phyroman, whom started out as a street performer but ended up working more like a Robin hood archetype to make ends meet. the party I was in had a human life domain cleric, a dwarf oath of conquest paladin, a water Genasi druid, myself, and a human battlemaster fighter whom specialized in dual wielding longswords (his nickname was lawnmower). this was around the second arc of the campaign where we had to liberate a suffering town from a circle of about seven tyrant nobles. we had already made an dent in the circle by collapsing the house of first noble and the dwarf managed to defeat the second in a hand to hand honor duel so we were feeling pretty alright about our chances. However one of the other nobles, a rich trade master who the DM basically made the most punch-able man in the world, had apparently had enough of us and had hired a group of about 15 high class assassins after us. so the night of the attack the druid and fighter decided to go scout out some of the other high class buildings to see if the targets we were after lived or worked in them whilst the rest of the party bunkered down for the night in the tavern. halfway on the way back them get cornered by about 8 of these assassins in a back alley they took to try to hide from guards. at first we all had an "oh shit this is serious" moment which got even more scary when the it turns out the remaining seven were sneaking into the rooms we had to attack us in our sleep. this fear was immediately halved when it turns out that A) the genasi was a level 12 circle of the moon druid (as it turns out a giant scorpion can be very terrifying when you aren't expecting it) B) the dwarf paladin REALLY didn't like being woken up by four assassins C) the cleric wasn't actually asleep at the time as she was reading a new book she found and wanted to spent a little time reading it D) they only sent one assassin after me, albeit i was out of spells for the day so combat ensues and most of the assassins aren't doing so hot, poor rolls mixed with not so great AC ends up tuning most of them into a chalk outline, except mine. so this next bit requires a tiny side tangent, I don't play my character as the typical edgy rogue, my character is a charming, sassy, warm-hearted character who often throws out various mild taunts during combat (these can range anywhere from scathing to mildly flirty depending on the situation). with that out of the way we can now go into what my character was going through. I was blocked from my weapons out of spells and not wearing my armor so I should be an easy target right? wrong. My opponent could not roll high enough to hurt me no matter what they tried, this must mean I can capitalize of this right? also wrong, neither of us could hit each other despite everything that had happened. even so the assassin was startlingly good at preventing me from getting my gear so I had to try hand to hand (which I sucked at) despite this my character still tried to keep his persona up as a being perfectly confident about the situation, throwing a few flirty taunts around, making a show out of dodging their attacks, all in an attempt to wear them out so he could get the upper hand. however the situation turned out to end far different then any of us expected, near the end of combat I decide screw it and go for a grapple (i was trying to capture them for interrogation) nailed the athletics check, they fail theirs, I got them pinned down on the floor hands behind their back, DM does a roll behind the table and looks shocked at his result, this was were things went weird, DM has me roll a perception check , I get a fifteen, DM says the assassin seemed to be incredibly uncomfortable in the position we were in but it didn't seem they were in pain, this confused the whole party, I decide to test a theory, my character leans in and says "If you're to uncomfortable like this I could hold you in a better position", DM says to roll seduction, "oh shit, really?", roll a eighteen plus modifiers making it a 22 (i have good charisma), the DM rolls insight for them, laughs, then says the assassin seems to relax a bit an almost pushes themselves against my character, "oh fuck", as it turns out whenever a character makes a flirty comment or taunt during combat, even if they aren't actually trying to seduce the NPC, the DM marks a tally every five tallies he makes the NPC make a insight or will save to see if they fall for the flirts, apparently my opponent failed 2 during our fight and was having a real hard time trying to keep this serious and the grapple was the final straw for that. two more seduction checks and another failed insight later and we're in the bed together, DM says to roll performance, Nat Fucking 20, plus mods ending up being around 30, the whole table bursts out laughing while the DM tries to explain through fits of laughter how the situation for the night turns out. the next morning the druid, after realizing that my character hadn't gotten up to meet with the team to discuss plans, decides to come check to make sure I'm ok, and there she finds me and (the apparently female Drow) assassin still in bed together. this sparks an incredibly awkward morning wherein the entire party is a mixture of shocked impressed and mildly annoyed at my character for what he did the previous night. which culminated in the dwarf chucking a chair at him for never taking the situation seriously she ended up becoming a DM NPC for a while, through some careful negotiations and continued flirty, which made the rest of the arc kind of painful for the dm as having two rogues who specialize in differing tactic that ping off of each other surprisingly well can make both in and out of combat encounters trivial. unfortunately this campaign kind of died due to both interpersonal drama but the DM informed me that if the need ever came to he would bring up my character and her again as partners in crime

[@hourglass8090]

6:13 that's awesome.

[@gameygeemer4142]

In an astounding bit of bad decision in Exalted (aka Bad Decisions the game), I rammed a ship into a ship in our path. This ship had 5 Celestial Lions, a Celestial Censor, and an E7 Sidereal. The ram did 22 damage (a LOT) to everything inside. At Essence 7, the maximum amount if health a Sideral can have is 21 (14 normal, 7 dying) The Sidereal had an ability that allows him to shunt off consequences to other copies of himself throughout the multiverse, but every time he uses it he rolls 1 d10. On a 1 he just thinks he shunted off consequences to another copy of himself until the end of the scene. He rolled a 1, and the second we decided to not go into combat he evaporated into a pink mist

[@underscore8085]

Our DM home-brewed a one-shot to get us into role playing and to make us familiar with the rules of The Dark Eye (for example: Nat1 = crit success, Nat20 = crit failure and validation roles for crits). The story is basically that the big ridiculous sporting event is coming to a small town, but that town's team went missing so our characters have decided to jump in. In our second session we are faced with the first game: beer-barrel-benchpress. Two team members are chugging as much beer from 2 barrels in 2 minutes as they can and then a third one has 15 actions to benchpress these two barrels as often as they can. Doing 15 strength checks in a row sounds boring, but hear me out: Around half way in my friends who's character is lifting roles a Nat 1. Validation role: Nat 1. Validation-Validation role: Nat 1. He succeeds at the third role without a Nat 1, so that means he triple-crits on his strength check. The entire table is losing their minds as our DM describes how his character is throwing the bar in the air three times, clapping each time. In the end our team not only won the game, but also secured bonus points because the King liked the performance as much as we did at the table.

[@lbpblitz]

I was running a githyanki creshe that the party was trying to infiltrate. The changeling sorcerer disguised themselves as a different gith who had come from the creshe and rolled a performance check to pass themselves off as the original. They rolled pretty low, only getting an 11 total. I rolled Insight for the two gith at the door. Double Nat 1s!! They immediately bought that this was a missing soldier and unlocked the door, at which point our two rogues made short work of the guards.

[@guanglaikangyi6054]

The players were invading a vampire lair where they fought a vampire with a cursed hand grafted onto him. It had a vorpal like effect that pierced the target's heart on a nat 20. First attack on the combat, I rolled a nat 20. It wasn't a big deal, there was a cleric with revivify. But immediately after, the cleric rolled a nat 1, which provoked a opportunity attack. I rolled another nat 20. The last player ran away.

[@silentxiii9496]

Unluckiest that happened at our last session. My brother, the DM of our campaign, rolled with advantage for an enemy skeleton. He rolled two nat 1s so he said, "The skeleton misses you and hits its own foot. Killing itself instantly." We had damaged the skeleton before this but it was still funny.

[@dwaynemontgomery1851]

OH ive got one for THIS! when a goul attacked my shadow sorcerer, he ended up criting me with the killing blow ripping my head off, i pointed out that my "strength of the grave" ability works even if im killed outright, but the gm gave me disadvantage and i had to roll an 18 or higher to survive, i rolled an 18 and a 19 and then just grabbed my head from the goul and put it back on, after the fight i cut up the goul for food out of revenge

[@ghostyuki-kfpinquisitor1038]

Was in an arena, the rest of the party was down or dead, got eaten by a gibbering mouther, managed to get 2 nat 20s in a row to barely kill it before it turned into a tpk.

[@lolusuck386]

One of my party members had his luckiest roll of his life in Shadowrun. To keep things short for the unfamiliar, Shadowrun uses exploding d6s. He's playing an adept martial artist and rolled a 23 on a exploding d6 to jump from a building and punch a helicopter, destroying it in a single punch. He even managed to stick the 20m landing with only serious wounds instead of flat out dying.

[@tomaspellizzere1184]

I'll make it short because its way too long. I once had a Monk who was kinda corny and did stupid stuff. His "signature move" was scream DRAGON UPPERCUT while doing just a normal random attack action. We travelled to the past and the DM made us roll to see how much did we alter in the future. We rolled percentile. I got a 100. When we came back there was this whole martial art that was based on my character and these people were all doing dragon uppercuts and shit. It lasted for a lot longer than it should. It was way too funny

[@murakumo65]

Savage worlds playing with homebrew races based in Egyptian mythology. The party was sneaking closer to an enemy camp to eavesdrop and get more information and avoid combat if possible. In order to get close enough to hear anything and not get caught we had to make a stealth roll of 6. Another player at the table was playing a cat person and critically failed his trained stealth roll twice while rolling a d10 +2 for his check. Mean while I'm playing a anthropomorphic hippo man and don't have stealth trained. I'm rolling a d4-2. The only way I'm making the check is rolling a 4 twice because of the exploding dice rule in the game. Rolling max value on a dice lets you roll again and add the results. I rolled a 21 after the minus 2 penalty. There is apparently a new bolder in the enemy camp that on one noticed.

[@Crystalline_cos2548]

Two PC’s in my party were pretty famous (members of nobility that attempted a coup and are now on the run bc the coup failed), so my DM introduced a mechanic where at the start of every session, the other players would roll insight to see if they recognised them, but there were only three other players and it was only the first time doing this so we probably weren’t going to get high enough to recognise- I roll a seventeen. And my character says nothing.

[@assassincharizard]

I'm a DM. I was doing some prep work the other day and rolled a D100 on the benefits and detriments tables for a magic artifact. 3 nat 100s in a row.

[@SkadiaXD]

I rolled 2 nat 19s and a nat 20 in a row on stealth... to hide from my own party (I was memory wiped because backstory reasons and thought these weirdos had come to kidnap me. Which they had. But for a good cause). What was supposed to be a half hour breakout turned into the entire session, the DM just giving up and playing the Benny Hill theme in the background, and so, so many shenanigans. There were maid outfits. Construction workers. The fighter rolled a nat 20 intimidation and flexed his shirt off. I consider myself lucky to have been able to prolong the shenanigans for that long.

[@Hive-Mind-BBX]

Rolled poorly for six turns... Rolled double 1 on a search action (we were doing a homebrew free form WH40 combat situation crawler, so searching mid combat was fine if the character wasn't in melee) GM gave the party a goddamn predator tank. Not like that pity tank didn't save us ALL from being tpk'd after getting it, we were fighting against a Chaos Lord in Terminator armour... With a particularly nasty weapon you may have heard of, called... The Black Mace. If anyone was close to someone who got hit by it, they took damage as well by mere proximity to the newly wounded, and 3 of our 4 characters only had 1 wound to work with at the time. So about 2 hours of giggling stonerness and a turn later, whoever ended up controlling the tank rolled all 5+ on rolls to hit, then all 6's on rolls to wound, outright killing the Chaos Lord, who until that point was essentially playing a murderous game of tag with three space marines and a space marine captain... All fleeing in terror to pop shots off at the impending doom that is The Black Mace.

[@neas033]

I simulated a Russian roulette game with a D6 die representing a six barrel revolver. Me and the other player decided to put the bullet in the third chamber. So I said, "whatever you do, don't roll a three." Tensions were high. And what do you know, first thing Master Sid rolls the dice and it lands right on three like a flaming, firing, FLYING DISCUSS! I was stunned, it all happened in slow motion. He said I had to roll 88 on a D100 to prove that he shot himself which I did not. So of course the Master Sid used slight of hand to make it look like he put the bullet in the third chamber. Since then I've learned to cheat rolling a D6 you just kind of spin it in a "discuss" motion to make it look like a roll. Which I taught another player when we went gambling with our treasure. I gave the NPC's a wisdom perception check to call us out on our cheating lol!

[@thaliaokamura4989]

Playing a dnd campaign, I was the artificer who was transformed into a guy in the fairy world. We went to the last labyrinth zone (festival booth), big spider comes up. Under tumbled stuff and with spider web on us, i aimed my crossbow at the spider and wanted to hit it. DM said: "You certainly can try." *Rolls a nat20* DM: Anika (my character), it's at a disadvantage... Roll again... *Rolls again a nat20* The party goes like: "THERE IS OUR PROTAGONIST!" And DM was like: What the fuck vibes! (All laughing at that point). It's still funny to remember that. Did not kill the spider outright but it was so funny that we often joke.

[@morphadomus2385]

I got a 1 out of a d100 on a divine intervention to bring back a friend who got disintegrated by a death tyrant. I've used that skill many times throughout the campaign, and I fully expected it to not work again, but it seems the dice gods and Bahamut smiled upon me that day.

[@hilmarheathkliff9511]

once saw a double nat 20 with disadvantage on a saving throw. same player rolled 4 nat 1s in a row later that session.

[@12107dc]

Playing Pathfinder 2e: we were in the middle of fighting some higher level ghouls. Our investigator had gotten to the final stage of a drowning disease effect and would die die if they failed their next fortitude save of which they have a minus one of the stat. I'm talking they need a 19 on the die to even succeed. In a last ditch effort to save the investigator i draged them away from danger and use my last remaining hero point to substitute nature for a medicine check. Nat fucking 20 bringing our only healer back into the fight.

[@dj_izaco8435]

Rolled a nat 20 on a roll to find out my powers came from a elder god. So that was cool.

[@isaacporter6450]

One time my party was tasked with getting a severed humanoid hand. Not a specific one, just any hand. So two goodie-tooshoes and a more logical dark player (let’s call him Patrick) go to a morticians to get a hand. Well it turns out they can’t get a hand so Patrick stabs the worker and begins casting cantrips on him so he can subdue him and remove his hands. goodie-tooshoes immediately start panicking and begin attacking Patrick and Patrick stops and says “if you can get a hand in 10:00 I’ll spare him” so goodie-tooshoes #1 sprints off to do so. 10:00 minutes pass and there is no return. Patrick begins to kill the injured worker while goodie-tooshoes #2 begins attacking Patrick and Patrick (supposedly) kills the worker and tears of his hand. Patrick casts expeditious retreat and sprints off. Goodie-tooshoes #2 casts longstrider and sprints after him. Since longstrider is faster then expeditious retreat, goodie-tooshoes catches up to Patrick and tackles him. This is a tense moment so I make them both roll to see who gets up first. No ability modifiers, no nothing. goodie-tooshoes #2 rolls a 19. Patrick sits there in disappointment as he nervously rolls his die. 20. He got up and shot goodie-tooshoes #2 dead and used expeditious retreat to return to the rest of the party. I thought it was pretty cool and tense. Somehow goodie-tooshoes #2 ended up permakilling Patrick later that session

[@houseofmartok4518]

1980: I was DM-ing a (1st ED AD&D) one-shot. PCs were hired to slay a Red Dragon terrorizing the locals. They went into the complex, many-chambered dragon's lair. All my planning ended up being for naught, as the party Barbarian (to whom I had given a Sword of Red Dragon-Slaying) rolled a NAT 20 on his first swing at the Dragon, then proceeded to roll max damage! Max damage x2, which was then x4 by the Sword of Red Dragon-Slaying, killing the Dragon in SINGLE BLOW!

[@houseofmartok4518]

Years later, friends have asked me why I didn't fudge the results by giving the dragon more HP to keep the encounter going. Well, one, it didn't really occur to me. Two, I've never fudged AGAINST my players, Three, the party wizard died by dragon's breath on the same round, before the barbarian's initiative came up. And four, I didn't want to take the joy of that incredible victory away from the barbarian player because they had already seen the bug-eyed, shocked expression on my face at the moment it happened, & I simultaneously blurted out "YOU KILLED IT!"

[@maSkizles]

My party of four level 14’s has been chasing around the BBEG that knows portal magic for 4 IRL years of campaign. They are finally fighting him as they interrupted a battle where the BBEG was trying to assassinate their strongest ally, the pirate lord. The BBEG was fighting the party, the pirate lord, and the first mate. The first mate is a friend they’ve had for about 2 of those four IRL years. The thing is, the BBEG is an ancient black dragon and thus has three attacks per action. The BBEG crit…three times in a row, on the first mate, instantly killing him.

[@maSkizles]

Two years before this event, they defeated one of the four necrolords, lords of death, that was corrupted and the other three hired the party to fix their friend. Upon his dying (hah) breath, I had the corrupted necrolord grapple the Druid (who had antlers) pick him up, and use him to beat the paladin as he fell for flavor because if it hit, it would’ve knocked him down. The thing is, the necrolord crit, and instantly killed the paladin. Thankfully the rogue had slipped a seal of undying into the paladins bag that they got from a previous adventure. The rogue thought the paladin was acting too cocky before the fight and felt it was smart to sleight of hand it onto his person. Probably one of the most cinematic moments in the campaign.

[@garywilliams5718]

This one requires a bit of context: So my brother had designed a completely new system for Feats, ASI, Short Rests, etc. He wanted to try it before he and his buddies were shipped to Iceland and had got some of his army buddies, our uncle, and me to have him test it out now at this point two or three of our party had left during the game and but we continued on even though that it was hard we had come across this monster a giant iron golem/sentinel thing, it was getting late and there was only three of us remaining still playing, We had a Monk, a Paladin and me an Evocation wizard so, my brother simply had us take straight towards the final boss a lich of sorts without a phlyactoery (sorry I forgot how to spell it) and he had knocked out the golem we rolled for initiative and I had rolled the highest so I decided as a hell mary attempt to try to revive the golem and tried to get him on our side, (I was low on health and spell slots) so I cast shocking palm to awake the giant and try to get him on our side, this failed spectacularly and got another enemy on the field, fast foward several rounds and our Paladin is down I'm almost down and our monk is close to down but is putting up a hell of a fight it comes to my turn again and I have a brilliant idea, because I was right next to the golem I decided to roll an arcana check against the golem to see if I could reprogram it to see us a friends, he tells me I can but the DC will be high, I roll and with the modifier I get a whopping 23 on the dice roll, I soon go down after this however because of what I did our monk was able to pull off a victory (P.s. this might not seem like much, but I am the Dm most of the time because I have my own group, and because of our hectic schedules, I don't get to play that much, sadly, however the others in our group have expressed interest in DMing so, maybe one day I will get to be a player again

[@A.R._Ironstar]

Mix of the best, and worst rolls I've had at once. Party boarded an air ship, my Barbarian a former pirate captain, along with our bard, convinced the mostly pressed crew to mutiny. The air ship's captain was an artificer, they had a bodyguard force of loyal warforged, her "children" that she had made by hand. We fight through the warforged, pushing past and leaving the rest of them to the crew, and storm the command room, as we beat down the door we see the ship's captain get into a mech suit. A long and brutal fight follows, grenades blow a hole in the hull, our warlock gets electrocuted into unconsciousness, bard is bleeding out, our artificer is doing their best to keep them alive while the wizard and my barbarian square off against the mech. Wizard blasts them with ice, and my barbarian smashes her maul into the frozen surface of the mech, shattering the plating and exposing the dwarf inside. My barbarian charges the mech, and roll to grapple, intending to pull the dwarf out through the hole. Our DM asks am I ***SURE*** I want to do that, and I of course say yes. Charging the mech, my barbarian slams into it and I make my roll, and I roll a nat 1. Mech throws my barbarian against a wall and rips off her right arm, leaving her to bleed out on the floor, and turns to face the wizard. I'm not done yet however, as I'm a half orc so I have relentless endurance, and thats not fatal damage, down an arm, I wait for the turns to cycle. Wizard backs up against the opposite wall, and drops darkness, our artificer manages to get the bard back up, the mech moves into the darkness, missing their swings against the wizard, and its my turn again. I get up, and once again, charge the mech and roll to grapple the dwarf our of the mech suit, this time managing to pull her from it, and beat her skull against the suit until she stops moving. Its over we think, and start to pull ourselves together. Then we hear a beeping coming from the mech suit. Artificer goes to investigate, and quickly figures out that the mech suit was linked to the dwarf's life. Her death started a count down, for a fail safe bomb, large enough to blow the air ship in two. We are told we have 2 rounds until it detonates, up to us in what order we make our moves. Artificer tries to disarm the bomb and fails, wizard goes to check on and warn the crew we had mutiny, warlock is still unconscious and our bard is trying to patch up the bleeding from my arm stump. Now, I think that my barbarian is basically dead at this point, missing an arm and if nothing is done the bomb will do us all in. So she gets up, and I ask to drag the mech suit over to the hole we blew in the hull, intending to throw it out. I roll my strength check, and drag it about half way to the hole, being able to move it less than I would have liked due to only having the one arm. Artificer tries one more time to disarm the bomb, and fails again. I roll to drag the mech again, and get it almost to the edge of the hole, not quite far enough to throw it out though. This is it we think, we don't have anything else to get it out of the air ship. Then the wizard storms back into the room, sees what's going on and casts haste on my barbarian. DM allows me to take the haste and move again. My barbarian backs up from the mech, and runs at it, slamming full body into the mech to make an unarmed charge attack at it, DM has me roll, saying "it will take a high roll to push this thing out" And I get a nat 20. Both the mech and my barbarian go flying out of the hole as she slams into it and kicks it away mid air. I think to myself, this is a good death for the character, she saved her friends, and she saved people from glorified slavery being pressed into the crew of an air ship. Then the bard jumps out after my barbarian, and casts featherfall on the both of us, and we begin to slowly drift towards the ground. The mech detonates far enough away that no one is harmed, and the crew have mopped up the remaining warforged. The bard and my barbarian land in a forest, and have to navigate our way out, while the warlock, artificer and wizard dock the airship, take the item we needed from it, and start to search for us, we end up meeting up at the outskirts of the next city, where my barbarian gets a mechanical arm crafted.

[@redspyro4750]

Rolled a nat 20 when I was about to die. Then rolled another two for heal rolls. Safe to say I kinda overhealed myself. And, due to my character starting with a item that converted half of healing into damage, I kinda nuked the enemy we were fighting into the ground, being the only living player in that run to actually kill something with a heal roll. Subsequently I had to nerf myself after that, and now if I got two nat 20 rolls in a row it flat out just nukes things even harder. Not to mention it now does damage to me for the amount of damage I do so... Yeah my friend, who was pure built for healing just used me as a conduit for damage. Next few encounters ended with me nearly dead in both, only surviving due to a item I found some runs ago that would save me from death once every rest. Luckiest sessions of my life

[@calebmccoy-ll4qw]

my first time ever playing D&D it was a like 15 minute oneshot to kinda show me the ropes and i rolled a damn ONE HUNDRED that so far has been the only though

[@electriczombie2573]

my party had just survived a fight with a white dragon in its lair and it had little kobolds as slaves. so after finding out they would have to leave and find a new place to live after the dragons death, my character Tal (half orc fighter) asked if he could make a charisma roll and speech to maybe get myself a little squire. nat 20 😃😄 i did my speech, something like 'you can be more, i can take you to the top, you will never sit in the dirt again' DM did not want me to add another creature to initiative so he said "a tiny little arm shot up and the body attached shouted one of the few common words it knows... yes!" a 3 year old kobold child ran out and held out her little hand 🥰 the kobold elder in charge said her family was crushed by the dragon before she was hatched so i wouldn't be breaking up a family and that's how i got my daughter in our homebrew game

[@rebeccakaras2572]

My luckiest dice roll was actually a nat 0. My 11 year old barbarian with the mind of a 5 year old was mind controlled and instead of possibly killing my party, I threw my weapon, chased it down without being able to hit anyone and my exhaustion caused me to pass out.

[@obiwancc]

Not D&D, but Cyberpunk Red. The way rolls work in Cyberpunk Red, for those unfamiliar, is you roll a D10, and add on whatever modifier from whatever skill you're using, and if you roll a 10, you get to roll another D10 to add on to that, and vice versa if you roll a 1. Now, for the story. Our party, or gang, or whatever you wanna call them, was in the process of robbing a rival gang of a whole bunch of cybernetics, weapons, and whatever other Night City goodies there are. My character went to the upstairs part of the building to distract them while the gang was getting prepared, and I made an Acting (deception) roll on them to try and convince them that I was with them. I rolled a 10, and, with a combination of the acting stat I had, and using luck points, I rolled a 39. Needless to say, the robbery was a success.

[@raigom8691]

Last week my Party played a Level 20 one shot and Faced Vecna. Our cleric read a book and was dominated. He casted dominate Monster on my Barbarian. The dm asked me for a wisdom save DC 22. My wisdom was +2 but I had disadvantage due to a curse. If I would get dominated too, the fight would be lost. I manage to roll 2 nat 20s in a row and saved the day

[@billbishop6109]

I’ve had several with my half orc barbarian. First session I rolled a double nat 20 on roll20 for an athletics check to disarm. Another time I needed to roll a 19 wisdom save, and after 3 rounds of garbage I announced “Okay here comes a 20!” Yep. Another time I was holding a corridor from waves of undead. I eventually was knocked out but came back with a DC10 relentless rage roll. Hit again, made the DC15 roll. Then the DC20 roll, then the DC25 roll. Managed to get healed after that.

[@billbishop6109]

The wildest one was when I was facing 3 large constructs playing the Canopic Being adventure from Candlekeep on Foundry. We finished them off in under 6 rounds, and in that time I rolled 4 nat 20s and 2 nat 19 crits with my vorpal greatsword doing something like 380 hp of damage by myself.

[@Totally_Baked]

Party was fighting a lich. I the barbarian grapples the lich my first round, and the second round I kissed him. Making him unable to cast spells the require V or S. I rolled 3 nat 20s in a row. The first to grapple, the second to force a kiss. And the third oddly was charisma and the lich ended up being into it. The DM was both laughing, stunned and slightly annoyed since the encounter was supposed to be way harder. One of my tables iconic moments we wont forget.

[@skyguard1an]

In my last campaign, we went off to different plane, in order to train ourselves. It was a very dangerous place, that would have killed uss, by *Making uss want to stay there* we where warned that it would be emidiate character death if we accepted the mission, but failed so we needed good rolls, my roll was a little bad, but against my teams insisting on me using my bardic inspiration, i figured itd be enough, and kept the roll. Turns out i hit EXACTLY the minimum of what i needed to resist.

[@user-ce5sh5bd4f]

My teacher gave us a probability assighnmet to roll dice, i rolled 2 20s after 20 rolls at disadvantage and no 20s at advantage

[@alejandrocamberosrodriguez4222]

I've got a couple. The first one was for my first character (a Monk, Khan): our party had been invited to a party after helping to retrieve an "extremely important" magical artifact from the capital city in our kingdom. In this party, we encountered an NPC from the first location we visited during the campaign: an army captain called Elizabeth with whom Khan had exchanged pleasantries and with whose soldiers he sparred a couple of times. At the insistence of my party members, Khan asked her out to dance, and she agreed; even though he wasn't a gifted dancer ("competent" would be a good word), they had a nice time dancing and later went to a balcony to talk and get some air. Our DM had us roll a d100 for what the night would entail for us: our Wizard kept mingling with other wizards, our rogue got lucky, and Khan rolled a 69 (nice). My DM knows me and, even though I'm no prude, I told him that Khan wouldn't go that far with someone that quickly: so under the soft glow of a full moon, Khan got his first kiss. And Elizabeth... apparently liked it.

[@alejandrocamberosrodriguez4222]

The second one was with my current character (a Dragonborn Paladin, Althan): we were fighting off a Demon/Devil invasion (yes, both of them), and we had to face off against 2 Behirs. As the party was split, each group had a Behir come in to attack. Since my Paladin, our Warlock, and an NPC were being targeted by this Behir, we rolled initiative and my Paladin was last, immediately after the Behir. The creature attacked the NPC who was next to me, and given I chose the Protection feat (and was wearing my shield), I imposed disadvantage on both of its attacks, and it failed both. My turn came up, and I rolled to attack: *Nat 20*. My Paladin has a Vorpal Longsword. I described the action flow: *you see the Behir attempting to bite (the NPC) but a shield appears from his side, and repels the attack; it goes in for a 2nd bite, and is repelled again in a swift motion. Then you see Althan, looking at the creature and speaking to it in Draconic "I am here to protect those around me, by the will of the Platinum Dragon, and you will NOT harm anyone else!", as his sword moves upward and cuts the Behir's head clean off* May not be *the* most legendary Nat 20, but man! It felt awesome!

[@travisdillman5600]

Not completely a Nat 20 story but... My DM splits the party FF4 Leviathan style to run a series of solo sessions with each of us. My half-orc Champion Fighter/Zealot Barbarian gathers a small group of NPCs for a 2 session dungeon crawl. I reach the dungeon boss and on the second turn I roll a Nat 20 Crit, second attack normal hit, ACTION SURGE, third attack 19 Crit, fourth attack Nat 20 Crit, Great Weapon Master bonus attack Nat 20 Crit. Dealt 147 damage in only one turn decimating over half of the dungeon boss hp.

[@jonathanmarks3112]

First time creating a character, first 4d6 roll. 6,6,6,6. Then it happened again with the character I created in another campaign. The odds of that happening once are one in 1296. The odds of that happening twice are one in 1,679,616. First time was with an app, second time with physical dice.

[@luciferandassociates9255]

Mine is slightly backwards. My character was a smooth talking Rogue with really high charisma skills. They weren't able to roll under a 20. Unless! They weren't talking to their parents. My character was able to lie through a zone of truth but when trying to lie to their mother or father would always roll a nat 1, and my DM allowed it as a failure because I liked the flavor that my character was just incapable of lying to their parents. It happened nine times. Nine Nat 1s to try and lie to their mom or dad.

[@demonteddybear3510]

Wow.... Sounds like I just had bad games. No wonder I took a break for 20 years, and then tried to play again just to roll a 1 on the kind of DM I would get. My luckest rolls: Helga the Serpent Tongue was in a rage after being forced teleport by another PC into a orge army before the other PC teleported themselves back to safety (As I said in another comment the team Wizard wanted the magic sword they can't use for their collection. My first magic item after two months of play (Everyone else had magic weapons and most creatures we faced were only effected by magic weapons.).) My dice were on fire. She was tearing the army apart when the general stepped up to face her. Two natural 20's followed suit and the general was one hit away from falling. Then my GM had the evil demon who was the final boss appear. Cut me in half with no chance to save. Then told me to make a new character. I quit after that.

[@benjaminroos2996]

In terms of helpful, my group has fairy **cough** fairly devastating rolls. When one of us nat 20s, most get at least a few that night. But we also have double nat 1s occur often. One member rolled quadruple Nat 1 (1/160000 chance) at a different table and shared a pic.

[@j-rod5930]

The party was helping Balders Gate fight off an invading army. We end up fighting off a dragon/hydra hybrid and our fighter ends up getting killed with the bottom half of her body being eaten. After we kill the monster I cast revivify on her which brings her back to life but she's still missing the bottom half of her body. Shortly afterwards we positioned ourselves to get a short rest we desperately needed. During said rest the rest of the party is trying to find a way to strap the fighter to her horse to help her keep on fighting. I ask the DM if my little goblin self can slip out to see if I can find a spell scroll of Regenerate. The DM reasoned that Balders Gate was a big place were magic was common and let me roll a d100. He let the group know I had to roll a 5 or lower and I managed to get a 3 to the astonishment of everyone. My goblin manages to find a ransacked magic shop with the spell scroll I needed being on of the few things not yet taken. I swipe the scroll and scurry off back to the party and bring the fighter back to 100%. We end up winning the war and in our characters epilogues the fighter and goblin end up getting together.

[@xenoshadow7575]

My party was fighting like 6ish? Trolls. I think we were like level 6 or something at this time. so for some quick contacts my character is a wizard that uses alchemist tools to make potions (so like health boosting stuff etc) the way they work is that i can use an action or bonus action to give or throw theses potions. this is important is because due to some shenanigans I essentially managed to get angry spirits in a bottle which on hit due 20 damage flat unless i roll a nat 20 which then I roll a d4 and depending on which one I get it increases the damage. so I decided on my turn i was going to throw one so i did. nat 20 then rolled a d4 got 4 did 80 damage and essentially one shooted this troll used my bonus action to throw another one at a troll.... Nat 20 D4 again.... Dm told me to roll again did the same thing two more times before I rolled like a 15? After this he made it that Everytime I roll a nat 20 with a soul bottle I get another action no matter what. Long story short I rolled the equivalent of 8 nat 20s and essentially one shot 4 trolls

[@gerbill13]

In a Rifts game ( dimension hopping isakai) First universe is fallout Rolling on a loot ( 1 is best roll) I get a pip boy with lots of plans and blueprint Get a nuka quantum Long time down the line impossible boss fight magi’s is nulled and non magical damage is halved I pull out the nuka grenade I made and ant man it roll for damage as it is inside the lovecraftian horror it counts as full damage Roll: 7777 I lost an arm But we won

[@JackRook]

Rolled a 20 to become mayor.

[@davidelin7680]

In pathfinder 2 the party was exploring an old temple and sudently we got attacked by some undead snakes, they were normal enemies and as a monk i started attacking one of them, sudently i see some rolls and they are ALL CRITS Crit on hit Max damage Max extra damage Crit on secondary effect The problem is that was the snake that bitten me... 3 sessions later my monk was still recovering from that accident (in pathfinder you dont restore all hp from long rest, you have to rely on old school medicine)

[@dragonriderabens9761]

party had some downtime between missions the previous session, my character had just taken a major step in character growth and had revealed a secret of his he's a dragonborn. in this world, dragonborn are often hunted by a band of particularly nasty bandits and slavers who have proven difficult to wipe out and turned into boots. they sell slaves to demons quite often. needless to say, they are not liked, and are not nice and due to the above his home was attacked by these bandits. it was not pretty. PTSD has him wanting to hide that he is a dragonborn around non-dragonborn. I asked the DM if there were any dragonborn waitressing at the inn/bar the party was calling home. he did what he called "consulting the dice of fate" apparently I rolled high because there was an entire dragonborn maid cafe not far from where we had this little reveal (it was a safe space for my character, making giving this reveal a little easier) he got blackout drunk and got the number (somewhat modern setting, so phones DO exist, but only in the heart of technology for the setting...which is where we call home base :3) of a cute red dragonborn lass. first date gets rolled and...nat 20. playing an artificer, and had preemptively flash of geniused it too. he didn't get laid by choice, and instead wanted this for the long haul. that nat 20 means him being off playing soldier for now won't do too much damage to that plans

[@truepridejb]

Playing battletech with work friends. Played 1 move 1 battle per day. I had a guy who could use an AC20(20 dmg) on hit. 1 day I Said “I’m gonna blow your freaking head off” rolled a head shot. 20 dmg to a 9 hp head. Instant death. Hilarious was what I said + the reaction.

[@TheHarzlek]

At my table that I Dm for We have a player and she plays a character named Willow a Woodelf Ranger and the amount of natural 20s she rolls is ridiculous one of our other players is Insane at keeping notes to the point where she will write down each dice roll. So she got the nickname crit queen because of the amount of natural 20s she would get in combat we decided to counter every single Nat 20 she rolled based on the notes my other player had written down. Keep in mind we have been playing the same characters almost every week for the last year and a half, Turns out 40% of all of her attack rolls are natural 20s.

[@TheHarzlek]

We decided to look into this because one time in combat against one of the final bosses of Arc two (Which was a possessed statue of a war hero taken over by had crazed wizard). She got five natural 20s in a row we even checked her dice Nothing weird about them at all as every time I roll her dice I always get natural ones

[@theoverpreparerlamenters3r436]

not mine personally, but someone in my party rolled three natural 20s to see if another party member was lying the first three times. This is still going on, so it might get even luckier.

[@spartanhawk7637]

I keep critting fort saves against stupid things like smoking pipeweed. It's become a joke that my dwarf cleric was just such a party animal in his younger decades that nothing does anything for him anymore.

[@darcraven01]

my lvl 5 druid lvl 5 monk did not roll any lower than an 15 on the die for every stealth check i made with him in my one shot a few weeks back.. having a +8 to my stealth checks means i was a minimum of 23 whenever i decided to hide. since i was playing an ink black plasmoid we just kinda said he flattened himself and blended into the shadows and basically had invisibility

[@inkling457]

Was about to die early on when I rolled a nat 20 and tamed the giant albino centipede that was about to kill me. :) From then on, I had a pet centipede.

[@BlackWolfessUSCM]

I was down to 1hp on a boss fight. My ranger is allowed to attack thrice in one turn which i utilized. I rolled damge for all three arrow shots and rolled nat 20s in row that coupled with the bonus damage took the boss to 0hp instantly and saved myself and my party on occassion my sister likes to bring up my luckiest dice tolls

[@Randomuser-eb2zd]

My party did something really dumb, the dragonborn paladin found a dragon and decided to roll to try to draw the dragon. He rolled a 20 and drew a perfect detailed picture of uhhh its behind. He proceeded to seduce it and do the deed

[@enderskunk7515]

nat 20 death save on my babarian prevented a tpk just last session I don't know how our party of three level four guys defeated Flint (from bg3, tactitain dificulty, I think CR 7), a damm troll (that we were told was supposed to be an ogre, but our DM got the wrong statblock...), 2 Hyenas and I think it was 19 Gnolls (I don't know exactly, but something around 20) all at once... Granted we had the tarrain rigged with a lot of traps that cleared most of the gnolls, but I'm still very confused about how we took down that troll, especially since that party is not terribly fond of fire dammage...

[@Axie539]

I rolled both a 16 and a 17 on my stat rolls one time

[@Ian-zu2mt]

I contacted A god twice at lvl 2 :)

[@INFINITEDOWNER]

I got a nat 20 when I was on one hp I am a cleric with mods I guess and I was able to heal and kill all the enemies in one fell swope and I healed my team I was PRAISED

[@FiftiethFiber13]

Not me but a friend wanted a npc pair of pants they were cool pants he asked for them rolled a nat 20 he took off the pants to find another pair of pants they were curssed... i also put on the pants

[@BurroughsProductions]

Man some of these house rules are crazy. I just would never. Keep rolling for every nat 20? Dying if u roll 3 nat 1s? Just no. I can not tell how robbed I would feel if the bbeg rolled 3 nat 1s and just died

[@berrie2981]

'promosm'