Not so much the nat 20 itself, but fighting a BBEG a couple sessions ago my rogue got one on a dex save against meteor swarm, and it's kind of funny trying to imagine how dodging a meteor impact works.
Then at the end of the fight, after having almost all my attacks miss, all my arcane trickster spells resisted, and the one hit H had landed getting really bad damage rolls, it was gratifying to then get the killing blow with a crit dealing 60 damage total with sneak attack factored in. (Level 10 for reference, and said BBEG was responsible for her father's murder and a lot of other bad stuff that happened in her life to boot.) Not so much a funny moment as a cathartic one.
Our adorable half dragonborn half halfling wizard has also gotten a few clutch nat 20 persuasion rolls in the campaign and we all imagine him having these big irresistible puppy eyes now.
The perpetually-stoned druid found a ninja costume and decided to sneak up behind my monk to scare her. Her instinctive reaction was to punch him in the face. Nat 20, max damage, and we were level 1 so it knocked him straight into death saving throws and the cleric had to come save him. His player decided that she had punched the high right out of him; he woke up sober, but with no memory of anything since the first time he smoked back at Woodstock (our campaign is set in 1983).
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Jude, He/They
Former gnome evocation wizard and dhampir fey wanderer ranger, current simic hybrid aberrant mind sorcerer
The perpetually-stoned druid found a ninja costume and decided to sneak up behind my monk to scare her. Her instinctive reaction was to punch him in the face. Nat 20, max damage, and we were level 1 so it knocked him straight into death saving throws and the cleric had to come save him. His player decided that she had punched the high right out of him; he woke up sober, but with no memory of anything since the first time he smoked back at Woodstock (our campaign is set in 1983).
Everybody go home, this one wins. Let’s pack it up.
I have two moments that I thought were really funny/entertaining.
We were playing Curse of Strahd and were trying to collect the Wizard of Wine gemstones, I'm a Gloomstalker ranger. So we go to the woods and I use detect magic, it's in the wooden effigy of Strah, and our rogue gives us the heads up that the place is surrounded. Great. We head back out to come up with a plan. We decide that I should disguise self as Strahd and just yoink the stone while everyone else hides. I cast my spell, walk back in and take it. DM has all the baddies jump up and start chanting and I say "Please wait my children, we can not carry out the ritual today. The weather is not auspicious."
DM: "Roll for Persuassion."
Me: "Nat 20."
DM: "..........They say okay and you take the stone."
The other moment is more recent, I am playing a halfling monk. Party is walking along the road and we come across an overturned wagon.
Leonin Artificer: "I'm going to try to turn it over."
Me: "Me too, I'm helping!"
DM: "Roll a strength check."
Leonin: "12."
Me: "Nat 20."
DM: "Okay! You just see the halfling go over and throw this cart upright and you hear some rattling inside and people shouting."
My party and I had just walked into a green dragon lair. The dragon begins talking with us warning us not to enter his lair. My party then decides to start talking with the dragon and gets the dragon to start monologuing. I decided to go up to the giant crumpling tower and begin painting a huge hole in the side of the tower with the marvelous pigments i just found on our last session (DM forgot i had these). The dragon begins to attack a short while later and gets in surprise breathe weapon attack and lands on a building next to the tower. We rolled for initiative and the dragon rolled a 2. The monk which rolled highest uses his ki to attempt to knock the dragon prone and outrolls the dragon on the strength check. It gets to my turn and i am currently counting out tiles on the board. the DM then asks what the heck i have been up to. i asked him, about how long has it been since we have walked into the lair? and he said about 10 mins. I told him, i have been painting a hole in the side of the tower since my character walked over here with pigments and then asked the DM can i use the web spell to shoot a string of web like spider man and pull the tower down? the DM pauses for a second and goes, i will allow it but your will need to roll a 25 on strength and you can pull it down on the same turn. (Thinking that by the next turn his dragon wont be prone and since i am an artificer i don't have high strength so it would be impossible for me) our dragonborn warrior's sees me shoot a web up the tower and his turn is after mine so he uses his turn to run up to me and i tell him what's going on and i tell him, he grabs the web out of my hands and starts pulling. he also got bardic inspiration before the battle, so he rolls his D20 and bardic inspiration. nat 20 + 4 strength + 2 bardic inspiration. The DM (Looking panicked now) goes i need to figure out how we will calculate the damage on this. and decides to use instant fortress damage 10D10 bludgeoning damage. Rolled 80 points of damage. Killed the dragon in 2 turns.
I had just gotten the spell “sleep” and we were in the middle of a fight with an owl bear, while we were all still level 3. So I run off into the forest to find a cricket, meanwhile one of my friends gets knocked out and another almost shoots them right after. I had to miss a whole turn because I was in the forest, but eventually I came running back yelling “I FOUND THE CRICKET!” And as the owl bear turned to swipe at me I cast sleep and rolled a nat20 and it fell to the ground. Oh and we also did that session without our main healer, and the only other one with a healing spell was me.
this next one is kinda the opposite of the question, bit I once rolled a 3 trying to throw ale into a fire, so I missed, but I hit a goblin right in the middle of the head, and killed it instantly, so… mission accomplished?
On the rare occasions we do seduction checks, the DM makes us and whoever we succeed with roll Performance just for fun.
After a hard fought victory and subsequent celebration party, my Bugbear propositioned one of the goblin NPCs that helped us win the day. Now, this was my third session of my first ever DnD campaign and the character token for her was a random half-orc woman he grabbed off the web. As a result, I knew that forgotten realms goblins were smaller than Bugbears but I thought they were around 5 feet tall and had no idea that they were, well...half the size of them or even less.
I rolled a natural 20 on the performance check and instead of having her roll one, the DM had her roll a constitution save where she rolled a 4. Her walking speed was halved for 1d4 days.
It's been two years and my friends group has never let me live down that moment.
I was playing a half-orc barbarian who was dumb as a rock with an aversion to being clean. We were in the Expedition to the Barrier Peaks and the party paladin had already found the space armor. They tricked me into a shower. While it was spraying and perfuming, I ripped everything apart, climbed out and walked up to the paladin with my fists clenched. he said, "I won't defend" to the DM. Nat 20. Knocked him out cold and dented the helm so badly it was useless to him. Took his potion of healing to fix my hand.
We have defeated the Gorgons. But 3 of the 6 party members were turned to stone. Each person was carrying (not wearing) some sort of anti-magic amulet.
Bard: Hey, what if we put the amulets on each of them and maybe that will help?
DM (eyes light up with pride): You can absolutely! But instead of disadvantage each petrified player will have to make a counter roll.
Artificer rolls: 19 ... petrified Rogue rolls - you guessed it - a nat 20
DM: The dice have spoken! Those were actually supposed to prevent petrification through this area, that's why I had you counter roll. But since the dice have so decisively eluded your attempts, the amulets will no longer be useful for that specific purpose.
As a DM, I was rolling initiative for a monster and got a nat 1. Fortunately/unfortunately, she gets advantage on initiative. The next roll? A nat 20. The players' screams echoed around the room when that happened.
Party was playing LMoP. The Half-Orc Barbarian ended up in a fight against two dwarves just outside the Stonehill Inn. After successfully restraining them *both* in a headlock, he asked me (DM) if he could attempt to smash the dwarves' heads together (non-lethal), so I ruled that he could roll an unarmed strike at disadvantage.
Nat 20.
Needless to say, the dwarves woke up with a pretty bad headache to say the least.
Can't remember the name of the one-shot, but the party was fighting zombies in a dungeon - not Curse of Strahd, I would've remembered that - and my character was a level 3 Gold Dragonborn. Guess who used his Breath Weapon on the zombies while three of his allies were too close beside the Breath Weapon's path. Needless to say, the pair to the left was a rogue and a bard who both failed the Dex save even though they both had the highest Dexterity Score at 15 each. The Life Domain Cleric to the right rolled a Nat 20. Gold Dragonborn means Breath Weapon deals fire damage, and my character dealt ~7 fire damage. You know how much hp rogues and bards have at level 3? Typically around 20 or so, which means a Breath Weapon dealing 7 fire damage would take out one/third of their hp in a single hit. In fact, our pesky bard immediately began death saving throws because of my character. I told him earlier to be careful with the Vicious Mockery cantrip; now he hates my character.
Full party of level 6 players, big bad was a CR 10 Shadow Horror. in a damp swampy dungeon, full of dark gloomies.
The fully Holy type level 6 single class Cleric saw the Shadow Hunter in stealth, got a surprise round on it before it attacked the party barbarian, the cleric got a nat 20 on a Guiding Bolt.
That is 6d6 (x2) doubled. (12d6) {max 72 min 12 averagish 48ish) they rolled well over 50. So double 55+ is 110+.
I use to roll the HP of my monsters...
A Shadow Horror has 120 or (16d10+32) it was under the average HP I rolled at something like 109. Our level 6 cleric one shot a CR 10 Large Aberration, in it's preferred enviroment, while it was trying to sneak up on a unsuspecting barbarian.
Way back in 1st/2nd Edition, I was DMing the party through a vampire's castle. The thief was looking around in the office room and heard footsteps coming down the hall. He hid behind the door and saw a figure come through. Backstab time! Rolls a Nat 20 and gets triple damage. If you recall, a backstab at that time was 4x damage, so now it is 12x damage. Rolls 8 damage, doing 96 total. Turns out it wasn't the vampire, it was his clerk, a normal human male with 4HP...
It was my first ever campaign. My DM gave my character an NPC bird (not to be a pet but a story guide) to help me and my other party members - both total newbs. I got Firebolt. I had no clue what this spell was. My DM would restrict my usage of it for TPK and such (new wizard and new player, it was inticing).
BBEG #1 takes my bird and keeps it captive. I have decided this is my pet now. It takes said birb into a room and shuts a wooden door - in a stone building. I've been rolling 5-12 p much my entire time playing (this was our third session). I, with all the fury of a wronged pet owner, throw my dice so hard into my dice tray, it bounces out and rolls under my bed. I dive under that bed to much screaming (and bashing my head on the bed slats) - I rolled a Nat 20 on firebolt on that damn door, got to take the birb back whilst the BBEG was in pure shock and get the hell out of there.
It was the first Nat 20 I ever rolled. She allowed me to keep the bird as a pet after that move.
We were in hysterics for about five minutes and had to pause the session.
It was my first ever game of D&D and we were all in 6th or 7th grade (and also new), so keep in mind the game was very ridiculous.
We’re in a dungeon for a reason I’ve long since forgotten. There’s a hallway ahead of us, and the rogue successfully identifies traps.
The fighter cautiously steps forward. Scythes fly out of the wall and he is killed by 12d20 slashing damage.
I ask the DM if I can make a perception check to find “boots of trap immunity”, something I made up on the spot. Because I am in sixth grade at the time, I am smelling for them.
I roll a natural 20, and the DM says I’ve been wearing said boots this entire time. So I crossed the hall while everyone else tried to make their dex saves.
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There is something that kid have that make them perfect for roleplaying
Hi everyone! I'm working up the will to finalize my signature, so... I guess this will be the signature for now
Innocence?
Ignorant bliss?
Imagination?
The untainted joy of youth?
Hubris?
Really you need to be more specific.
Farewell.
I guess that
Hi everyone! I'm working up the will to finalize my signature, so... I guess this will be the signature for now
Not so much the nat 20 itself, but fighting a BBEG a couple sessions ago my rogue got one on a dex save against meteor swarm, and it's kind of funny trying to imagine how dodging a meteor impact works.
Then at the end of the fight, after having almost all my attacks miss, all my arcane trickster spells resisted, and the one hit H had landed getting really bad damage rolls, it was gratifying to then get the killing blow with a crit dealing 60 damage total with sneak attack factored in. (Level 10 for reference, and said BBEG was responsible for her father's murder and a lot of other bad stuff that happened in her life to boot.) Not so much a funny moment as a cathartic one.
Our adorable half dragonborn half halfling wizard has also gotten a few clutch nat 20 persuasion rolls in the campaign and we all imagine him having these big irresistible puppy eyes now.
The perpetually-stoned druid found a ninja costume and decided to sneak up behind my monk to scare her. Her instinctive reaction was to punch him in the face. Nat 20, max damage, and we were level 1 so it knocked him straight into death saving throws and the cleric had to come save him. His player decided that she had punched the high right out of him; he woke up sober, but with no memory of anything since the first time he smoked back at Woodstock (our campaign is set in 1983).
Jude, He/They
Former gnome evocation wizard and dhampir fey wanderer ranger, current simic hybrid aberrant mind sorcerer
Rookie Call of Cthulhu Keeper
Everybody go home, this one wins. Let’s pack it up.
Farewell.
I have two moments that I thought were really funny/entertaining.
We were playing Curse of Strahd and were trying to collect the Wizard of Wine gemstones, I'm a Gloomstalker ranger. So we go to the woods and I use detect magic, it's in the wooden effigy of Strah, and our rogue gives us the heads up that the place is surrounded. Great. We head back out to come up with a plan. We decide that I should disguise self as Strahd and just yoink the stone while everyone else hides. I cast my spell, walk back in and take it. DM has all the baddies jump up and start chanting and I say "Please wait my children, we can not carry out the ritual today. The weather is not auspicious."
DM: "Roll for Persuassion."
Me: "Nat 20."
DM: "..........They say okay and you take the stone."
The other moment is more recent, I am playing a halfling monk. Party is walking along the road and we come across an overturned wagon.
Leonin Artificer: "I'm going to try to turn it over."
Me: "Me too, I'm helping!"
DM: "Roll a strength check."
Leonin: "12."
Me: "Nat 20."
DM: "Okay! You just see the halfling go over and throw this cart upright and you hear some rattling inside and people shouting."
Me: "Oops."
Current Characters:
Inara, Changeling, Level 3 Ranger/Gloomstalker
Oraine Bramblebrand, Level 5 Monk/Way of Ascendant Dragon
My party and I had just walked into a green dragon lair. The dragon begins talking with us warning us not to enter his lair. My party then decides to start talking with the dragon and gets the dragon to start monologuing. I decided to go up to the giant crumpling tower and begin painting a huge hole in the side of the tower with the marvelous pigments i just found on our last session (DM forgot i had these). The dragon begins to attack a short while later and gets in surprise breathe weapon attack and lands on a building next to the tower. We rolled for initiative and the dragon rolled a 2. The monk which rolled highest uses his ki to attempt to knock the dragon prone and outrolls the dragon on the strength check. It gets to my turn and i am currently counting out tiles on the board. the DM then asks what the heck i have been up to. i asked him, about how long has it been since we have walked into the lair? and he said about 10 mins. I told him, i have been painting a hole in the side of the tower since my character walked over here with pigments and then asked the DM can i use the web spell to shoot a string of web like spider man and pull the tower down? the DM pauses for a second and goes, i will allow it but your will need to roll a 25 on strength and you can pull it down on the same turn. (Thinking that by the next turn his dragon wont be prone and since i am an artificer i don't have high strength so it would be impossible for me) our dragonborn warrior's sees me shoot a web up the tower and his turn is after mine so he uses his turn to run up to me and i tell him what's going on and i tell him, he grabs the web out of my hands and starts pulling. he also got bardic inspiration before the battle, so he rolls his D20 and bardic inspiration. nat 20 + 4 strength + 2 bardic inspiration. The DM (Looking panicked now) goes i need to figure out how we will calculate the damage on this. and decides to use instant fortress damage 10D10 bludgeoning damage. Rolled 80 points of damage. Killed the dragon in 2 turns.
I had just gotten the spell “sleep” and we were in the middle of a fight with an owl bear, while we were all still level 3. So I run off into the forest to find a cricket, meanwhile one of my friends gets knocked out and another almost shoots them right after. I had to miss a whole turn because I was in the forest, but eventually I came running back yelling “I FOUND THE CRICKET!” And as the owl bear turned to swipe at me I cast sleep and rolled a nat20 and it fell to the ground.
Oh and we also did that session without our main healer, and the only other one with a healing spell was me.
this next one is kinda the opposite of the question, bit I once rolled a 3 trying to throw ale into a fire, so I missed, but I hit a goblin right in the middle of the head, and killed it instantly, so… mission accomplished?
On the rare occasions we do seduction checks, the DM makes us and whoever we succeed with roll Performance just for fun.
After a hard fought victory and subsequent celebration party, my Bugbear propositioned one of the goblin NPCs that helped us win the day. Now, this was my third session of my first ever DnD campaign and the character token for her was a random half-orc woman he grabbed off the web. As a result, I knew that forgotten realms goblins were smaller than Bugbears but I thought they were around 5 feet tall and had no idea that they were, well...half the size of them or even less.
I rolled a natural 20 on the performance check and instead of having her roll one, the DM had her roll a constitution save where she rolled a 4. Her walking speed was halved for 1d4 days.
It's been two years and my friends group has never let me live down that moment.
I was playing a half-orc barbarian who was dumb as a rock with an aversion to being clean. We were in the Expedition to the Barrier Peaks and the party paladin had already found the space armor. They tricked me into a shower. While it was spraying and perfuming, I ripped everything apart, climbed out and walked up to the paladin with my fists clenched. he said, "I won't defend" to the DM. Nat 20. Knocked him out cold and dented the helm so badly it was useless to him. Took his potion of healing to fix my hand.
We have defeated the Gorgons. But 3 of the 6 party members were turned to stone. Each person was carrying (not wearing) some sort of anti-magic amulet.
Bard: Hey, what if we put the amulets on each of them and maybe that will help?
DM (eyes light up with pride): You can absolutely! But instead of disadvantage each petrified player will have to make a counter roll.
Bard rolls: 16 ... petrified Ranger rolls - nat 20
Warlock rolls: 10 ... petrified Eldritch Knight rolls - nat 20
Artificer rolls: 19 ... petrified Rogue rolls - you guessed it - a nat 20
DM: The dice have spoken! Those were actually supposed to prevent petrification through this area, that's why I had you counter roll. But since the dice have so decisively eluded your attempts, the amulets will no longer be useful for that specific purpose.
As a DM, I was rolling initiative for a monster and got a nat 1. Fortunately/unfortunately, she gets advantage on initiative. The next roll? A nat 20. The players' screams echoed around the room when that happened.
pm me the word "tomato"
she/her
Lol
Come check out some of my Homebrew (please give input!)
Make some trinket tables on this thread!
Party was playing LMoP. The Half-Orc Barbarian ended up in a fight against two dwarves just outside the Stonehill Inn. After successfully restraining them *both* in a headlock, he asked me (DM) if he could attempt to smash the dwarves' heads together (non-lethal), so I ruled that he could roll an unarmed strike at disadvantage.
Nat 20.
Needless to say, the dwarves woke up with a pretty bad headache to say the least.
[REDACTED]
Can't remember the name of the one-shot, but the party was fighting zombies in a dungeon - not Curse of Strahd, I would've remembered that - and my character was a level 3 Gold Dragonborn. Guess who used his Breath Weapon on the zombies while three of his allies were too close beside the Breath Weapon's path. Needless to say, the pair to the left was a rogue and a bard who both failed the Dex save even though they both had the highest Dexterity Score at 15 each. The Life Domain Cleric to the right rolled a Nat 20. Gold Dragonborn means Breath Weapon deals fire damage, and my character dealt ~7 fire damage. You know how much hp rogues and bards have at level 3? Typically around 20 or so, which means a Breath Weapon dealing 7 fire damage would take out one/third of their hp in a single hit. In fact, our pesky bard immediately began death saving throws because of my character. I told him earlier to be careful with the Vicious Mockery cantrip; now he hates my character.
Full party of level 6 players, big bad was a CR 10 Shadow Horror. in a damp swampy dungeon, full of dark gloomies.
The fully Holy type level 6 single class Cleric saw the Shadow Hunter in stealth, got a surprise round on it before it attacked the party barbarian, the cleric got a nat 20 on a Guiding Bolt.
That is 6d6 (x2) doubled. (12d6) {max 72 min 12 averagish 48ish) they rolled well over 50. So double 55+ is 110+.
I use to roll the HP of my monsters...
A Shadow Horror has 120 or (16d10+32) it was under the average HP I rolled at something like 109. Our level 6 cleric one shot a CR 10 Large Aberration, in it's preferred enviroment, while it was trying to sneak up on a unsuspecting barbarian.
Way back in 1st/2nd Edition, I was DMing the party through a vampire's castle. The thief was looking around in the office room and heard footsteps coming down the hall. He hid behind the door and saw a figure come through. Backstab time! Rolls a Nat 20 and gets triple damage. If you recall, a backstab at that time was 4x damage, so now it is 12x damage. Rolls 8 damage, doing 96 total. Turns out it wasn't the vampire, it was his clerk, a normal human male with 4HP...
It was my first ever campaign. My DM gave my character an NPC bird (not to be a pet but a story guide) to help me and my other party members - both total newbs. I got Firebolt. I had no clue what this spell was. My DM would restrict my usage of it for TPK and such (new wizard and new player, it was inticing).
BBEG #1 takes my bird and keeps it captive. I have decided this is my pet now. It takes said birb into a room and shuts a wooden door - in a stone building. I've been rolling 5-12 p much my entire time playing (this was our third session). I, with all the fury of a wronged pet owner, throw my dice so hard into my dice tray, it bounces out and rolls under my bed. I dive under that bed to much screaming (and bashing my head on the bed slats) - I rolled a Nat 20 on firebolt on that damn door, got to take the birb back whilst the BBEG was in pure shock and get the hell out of there.
It was the first Nat 20 I ever rolled. She allowed me to keep the bird as a pet after that move.
We were in hysterics for about five minutes and had to pause the session.
It was my first ever game of D&D and we were all in 6th or 7th grade (and also new), so keep in mind the game was very ridiculous.
We’re in a dungeon for a reason I’ve long since forgotten. There’s a hallway ahead of us, and the rogue successfully identifies traps.
The fighter cautiously steps forward. Scythes fly out of the wall and he is killed by 12d20 slashing damage.
I ask the DM if I can make a perception check to find “boots of trap immunity”, something I made up on the spot. Because I am in sixth grade at the time, I am smelling for them.
I roll a natural 20, and the DM says I’ve been wearing said boots this entire time. So I crossed the hall while everyone else tried to make their dex saves.