D&D players, What is the funniest skill check you/party members have rolled?  

Apocalisse - John's Guide to the Armageddon for 5E www.kickstarter.com/projects/acherongames/apocalisse-johns-guide-to-armageddon-for-5e?ref=2g2etc

This reminds me of that story of the Druid turning into a horse to call the party's horse back and it turned out to be a mating call. "Roll for penetration."

Someone rolled to pet a chicken once. They got a nat 20 and the bird went careening into orbit.

Playing a Shadowrun campaign, one of our party members picked "Anime" as a knowledge skill, and pumped a LOT of experience to get it as high as possible. Almost any time that our party was planning something that required us to imitate some profession or specialized knowledge, he would make a roll and ask the DM "have I seen an anime about this?" The answer was almost always yes. Disguise ourselves as chefs to poison a prisoner's meal before he can talk in court? He's a master sushi chef who "accidentally" prepared fugu fish incorrectly. Disguise ourselves as fumigators here to clear out a bug infestation we may or may not have caused? He's the party's face and knows all the lingo and procedures. We get lost in the woods while a long range signal blocker is shutting down our GPS? He's an expert woodsman who successfully navigates us back to town.

Not exactly a skill check, but it's close enough! While our party's fighter, rogue, and palibard were helping stop a jailbreak in Waterdeep, our sorcerer and cleric were off in the City of the Dead with an NPC knight to deal with a necromancer. They managed to kill all the undead the necromancer summoned, but their target fled amid the chaos after getting wounded by the knight. Now, our sorcerer doesn't like leaving jobs half-finished, so they checked their spell list for anything that might help track the necromancer down. The closest thing they had was Detect Poison and Disease. Fortunately, the knight had the necromancer's blood on his sword, so the sorc cast the spell. The DM decided to roll d100 to determine if the necromancer had a disease in the first place. My brother in Christ, the DM rolled a 69. Through the hysterical laughter that broke out over the chat, the DM ruled that the necromancer had an STI, allowing the sorc and cleric to continue tracking the unlucky sod via his tainted blood.

We play over Discord and had just activated a trap with swinging axes, our Cleric had to do something real quick so we took a short break. When he got back into the call he said he backflipped over the axes before the DM even asked what he wanted to do, and rolled high enough and did it flawlessly. The ranger did the same because it was funny, same result. Then for the sake of being funny I did it as well, but got cut in the process because my roll wasn't as good. The DM just made the NPC with us do the same, and then proceeded to say we didn't even attempt to look around. I also rolled to pull a pressure plate out of the ground and nothing happened. No regrets.

I rolled two nat 20’s back to back when I was interrogating a bad guy. One for the actual interrogation and the other to use a disguise. I ended up playing good cop bad cop by just putting on a fake moustache when I was the bad cop and taking it off to play the good cop.

Described the position of guards in a room. I decided to do it through interpretive dance. I was playing a dragonborn bard. Nat 20. I described the position and what the guards were doing and even the furniture. All through interpretive dance.

We had “roll a con save for swallowing a cactus” and a performance or deception check for impersonation of a dead ally while magically disguised as him, at his own funeral… both the same character

I once rolled a 0 on a survival check. I rolled a nat 1 and had a -1 modifier. I'm surprised my character wasn't just killed. Granted that was the same character that rolled four natural 1's in a row in combat. I think that character was just meant to die.

Got a short and sweet one. Was playing a game I was a healer don't really remember but one of my friends where a barbarian, the only thing that matters is knowing I was definitely absolutely weaker than him. Mid battle we were on a tall and slender platform and arguing about how we would launch an attack on some enemy's below our platform. "We" (he rolled high to convince me) decided a slap contest was the best way to handle things. I went first rolled very low below 5 I think. He however reared back rolled a Nat 20 strength check and sent my limp body flying off the platform with a slap that put Zeus's lightning strikes to shame. Killing me as I fell now lifeless Infront of the enemy.

For those that asked about the last story being mine...I'll keep it a little brief. Mr Ripper, this is for you to... Argon had, some time after that gala gone on several quests, ended becoming the avatar of the God of justice, and tried to stop a war between the old and new gods with the help of the party of course. I had come back to Catherine's town as they were evacuating before the town was attacked and said my goodbyes to Catherine. She kissed me goodbye and said I had better come back to her. Later on I found out she was pregnant at that time and didn't want to worry me. Anyways, upon leading up to the fight with the mini bbeg I was power word killed by the mini bbeg and sent to the Neverending sands of the Egyptian afterlife. Whatever, I also ended up having to climb out of the 9 circles of hell to come back to life. Argon could come back to life if I was killed like that as long as I rolled well enough to survive. Anyways, I come back with a magic mcguffin and hand it to another party member. We end up winning the fight in an odd way but not important. But after using that magic item, after the fight, a portal opened nearby. A couple party members jumped through and only Argon was left. I had to choose. I said something along the lines of ..."well off to the next adventure ". Turns out that after the portal closed , we later came to find out we had been sent 20 years into the future. We found this out after we went to a nearby town for information. Guess who owned the tavern? Catherine owned it and named it the Drunken Owlbear after my pet Owlbear I raised named Trogdor. We sit down at the tavern and I notice the bar woman is a woman that's familiar and I little older looking. She looks back and eyes go wide once our gaze meets. I realize who I'm looking at and go over to talk to her. She throws a drink in my face and also hugs me and apologizes. After some talk and explained events, She mentioned she is married to a new man after all she thought I peaced out or died. But she also mentioned my kids Ghariel(Gary) and Gaviel( Gavy) my boy and girl twins. They are the half human and lizardfolk kids I mentioned in the ending story of this video. I get to meet them and gets to know them over the next few weeks. As an added tidbit, I grew close to them and then died in the belly of a tarrasque after being stabbed to death by a traitor teammate that wanted me dead or something like that. There was a huge funeral and Constantine himself pulled me from hell where I was tasked with punishment of sinners. I was pulled out to say my final goodbyes and mive on to the happy afterlife I deserved after all of my good deeds. This character was probably the only one that genuinely and visibly hurt me when he died as I poured alot of myself into this character. But maybe I'll bring him back one day. @russdarracott395

Some necessary context here: the group I first started playing with had a house rule regarding goblins. If a goblin ever rolled a nat 1 on an ability check they would end up accidentally killing themselves. This resulted in a lot of hilarious moments, and inspired me to make a series of goblin PCs. The DM ruled that for PCs a nat 1 wouldn't be outright fatal, but there would still be damage. Enter the goblin Stab Me, a level 1 barbarian wielding a long sword and shield that are both sized for a full-grown human, which he has to carry on his back. The party is in the woods and hears a pack of wolves. The secretive Shifter in the party decides to climb a tree for a better view, and the DM asks us all to make perception checks to try and notice her physical change. I roll a nat 1. The DM excitedly tells us how Stab Me keeps leaning back, transfixed by the site of my climbing companion. Leaning further and further, until I fall straight back landing on my shield and sword. While we all laugh at this, I decide that Stab Me doesn't have any reason to get up, so he just stays there until someone comes to get him. As our search continues Stab Me has a brief conversation with the Shifter (I don't remember the subject). The Shifter's player, a Kindergarten teacher, slips into her old habits and says something like "OK sweetie, I know you are just trying to help...." I literally stop listening to her and just stare at the player with an expression of idiotic glee. I smile and say "Sweetie?" Laughter ensues as the player realizes what she has unleashed. I'm mentioning this for context as we then reached the pack of wolves circling a merchant cart. Stab Me happily shouts "Puppies!" and runs over to a wolf. He then pets the wolf with his sword, then pokes it after it 'falls asleep'. He turns and spots the Shifter, and his eyes bounce between her and the wolf. I tell the DM I would like to drag the dead wolf over to the Shifter (we are still in combat at this point). DM points out the large weapon and shield I am already carrying, and that I am asking to grab and move a creature a size larger than me. I roll a 19, the DM facepalms, and I start dragging a wolf, a sword, and a shield over to the shifter. Combat ends before I reach her, and she promptly asks what I am doing. Stab me pulls the dead wolf forward and, with the look of an innocent child that thinks this is the greatest gift ever, says "Puppy for you!" There was much laughing and facepalming, a humorous tale was born, and I eagrely awate a new opportunity to play Stab Me or any of the other goblin characters I have made but never played.

Nat 20 to play secret tunnel on a lute

Our cleric went to brothel (yes, no celibacy oath) and found out that it cost 50 gp. So, she asked my PC (bard with smuggler background) if it was fair price. "- Do I know if it's fair price? - Roll [I don't exactly remember, what, but I guess it was history] - Nat 20 - Oh, you are an expert in this!" It actually turned more interesting way later. I didn't plan it, but just from how it was going, I realized that my PC was ace all that time (I was uncomfortable with roleplaying an opposite gender PC in situations related to sexual desires and came with pretty pathetic excuses for avoiding it; eventually I realized that it really made sense if he didn't want any, but wasn't comfortable admitting it). Which raises the question... Where did he know all that from? I mean, you don't need to use port wh*res' services to know how much it costs, but why would he verify prices in random red light districts or know how high-end courtesans work? My best guess is that he just does it out of curiosity or to annoy people.

My Drow Warlock needed to meditate. So I wanted to climb up into a tree. I rolled a nat 20 on acrobatics and found THE PERFECT branch. The DM described it as "The branch cradles your ass perfectly". Me and an NPC talked about taking turns resting on said branch.

PANR has tuned in.

Just this Sunday, one of my players made a skill check for hair growth ointment. Another player had a running joke where his chest was hairless until an earlier attempt at the ointment rolled low, giving him ONE singular hair. He guarded it with his life until he lost it due to breaking an enchantment/curse that had given him a temporary full chest of hair. Once it was disenchanted, all of his chest hair fell out, including the one. The druid rolled high on the medicine check and it sprouted THREE new chest hairs. He took the entire experience as a total win in the long run.

Not DnD, but Stars Without Number. Our group is a bunch of mercenaries hired to serve as bodyguards to a pair of alien diplomats as they traveled through human controlled space. During a big diplomatic meeting with influential factions from across the sector, we learn that our bosses were being targeted by for assassination by the local megacorp-disguised-as-a-mining-union (long story, pretty boring). So we're staying on the outskirts of the room the meeting is in, sneakily taking a look at the various camera crews and security teams that are on the outer rung with us. Eventually our resident space cowboy, Jaxas Macaw, spotted that one of the camera crews was *unusually focused* on our bosses. Since we didn't have the evidence to know that was a weapon and instead just had a hunch. So Jaxas declares he's gonna make it look like he tripped and "accidentally" knocked over the camera. Our GM wonders out loud for a little bit for what skills would Jaxas have to roll before suddenly blurting out "ROLL STRENGTH/BUREAUCRACY." The entire party started cackling after that declaration.

I have one. We’re playing Wolsung, a steampunk TTRPG with a bigger emphasis on storytelling than mechanics (most scenes have 1 roll at most, players start out as heroes and have “assumed equipment”, so you can just say “I have a grappling hook” if you are a character that would get a grappling hook). It’s a multi k6 system where a 6 lets you roll another dice. I was playing a dwarf born with a natural talent for fine manipulation pyromancy, making him into a walking plasma torch/welder. We were traveling with a train and the train stopped, so I rolled to see what he can learn from looking out the window and managed to get like 41 total out of rolling an initial 4k6. Suffice to say he diagnosed the steam engine remotely and rushed over to preform emergency repairs, which earned my dwarf a lot of local fame (with fame being a sort of currency, gained with “victories” and lost wil “losses”, though a victory by cheap tactics could count as a net loss and loosing honorably in a smithing contest with the nation’s best artisan can still be a victory)

Our party had just killed a corrupted Black Dragon, and we had plundered its lair of basically everything of value, weighing in at around 200 lb of gold, platinum and gems. My Bugbear, thanks to his Belt of Hill Giant Strength and his Powerful Build Feature, had a carrying capacity of 630 lb, so he was designated as the party mule for this particular haul. However, on the way back, we ran into an entire tribe of Lizardmen that had previously pointed us in the right direction of the mad dragon's lair. They had heard the beast's loud demise, and now they were here to claim the hoard, as they felt it rightfully belonged to their master. You see, they were servant's of the corrupted dragon's father, an Ancient Black Dragon that had grown tired of his demented offspring anyway and was just happy to be rid of it. but being a dragon, he still felt very much entitled to his brat's treasure hoard, even though we had been the ones to do his dirty work for him. Now at this point, we're outnumbered at least 2 to 1, and we're all beaten to hell and back, so we really don't wanna tangle with these fellows. But at the same time, we don't want to give up our precious loot either. We fought a goddamn dragon for this haul, for crying out loud! That's when our bard steps forward with a smile and cheerful tone, and informs them that the hoard is still safely tucked away in the dragon's lair, waiting for someone to come pick it up. She succeeds on a Deception roll and the Lizardmen are fooled by her honeyed words. However, my character is standing there in the background, back almost bent 90 degrees forward with sacks of gold and gems stacked on top of it and threatening to spill out for all to see. The GM tells me to roll Stealth with Disadvantage to see how well I can blend into the background and not draw attention to my obvious loot. As a Fighter, that really should have been the end of our deception. But again, I'm a Bugbear, and Bugbears start with Proficiency in Stealth and a bonus to their Dexterity score. My character was as much an ambush predator as he was a frontline fighter. I get a 14 on my Stealth check, a respectable number considering it's with Disadvantage. Then the Lizardmen roll for Perception to see if they spot me, and we all hold our breath. Nat 1. The Lizardmen promptly thanked us for our services and then walked past us to claim the treasure. At which point, we legged it as fast as inhumanly possible. And since then, we've never visited that area of the world again.

Angry Gnome artificer rolled for aiming and firing a trebuchet straight into the King's main hall during an evening party. The projectile was himself, riding an 80 kilos barrel of black powder, while on fire. Did NOT roll a nat20 but still good enough to hit the target. Was the revived after a few years in-game, became a vigilante (some rogue/paladin levels + extra backstory skills) and was known by most only as "Fire for Effect".

Late to share, but something my party found amusing at the moment. In the campaign I play in, I'm playing as a young bard, around 13 years of age. The rest of the players are various in races and classes, all adults according to their respective race. Our Dm had the party meet with an all knowledgeable Eldar Dragon to answer questions we may have had and possibly clue us in on future events. The party, after several descriptions about how powerful the dragon was, wanted him to join our adventure. Everyone rolls persuasion and rolls too low. Then suddenly, my character walks up, says, "Please join us," and then I roll. 19+4=23. A literal child had convinced an elder dragon to adventure with the party, all while using the all-powerful magic word.

A player of mine used to call out random checks as a joke. While walking, he'd say "Walk Check," or randomly say "Breathe Check" or the like. While camping next to a pit trap they'd avoided, he said "Eat Check." I had him roll for it, and he rolled a natural one, which, due to some house rolls, ended up as a negative number. He became violently sick to his stomach, losing the entire contents of said stomach into the pit. He didn't ask to make any joke checks after that. As an added bonus, on the way back, he nearly fell into the pit trap that contained his previous few meals.

I was playing a pirate bard, the group entered a town where the guards hated us for no reason (DM made everyone hostile towards us). Being a pirate I wanted to head to the tavern first and was going to play music when the guards showed up to arrest us. Bard shenanigans go on, during that I was able to convince them another guard left his post to track us down by using minor illusion. As we were making our way out of the town I passed by a random guard and asked to roll slight of hand, DM allowed it and succeeded so I said "Cool, I put a piece of paper in his pocket", when asked what it contains I said "Just one word, Cunt". The table erupted in laughter saying "what if that guard (the one I framed for abandoning his post) was known for doing that and that was why he was stationed at the entrance. Once they find the note a few other guards jump him." Staying in character I said "Bloody cunt has it comin to 'em for expecting me to pay to enter the town". A different campaign we were in some caves, came across a short NPC that had a cane. After killing them I took the cane, fast forward we had to do a series of acrobatic checks as we're running, hopping from ledge to ledge and other things like that. As I'm rolling I state my character is hunched over and doing all of this using the cane. Made it out with not only with a cane but with my pride intact.

Ah, yes. Styrofoam the barbarian!

Our party got arrested by the bbeg with a job that was a trap. Our rouge felt something was off and he suitcased a lock pick . While in prison he failed the roll to remove it and had to spend an entire night in the corner getting it out. He finally got it out and picked the lock rather easily.

Notable rolls in the games I've been in or DM'd: Roll to "knowledge local the lock open" by a rogue who'd neglected to learn, you know, ROGUE skills. Roll to attack: nat one. Roll to see what happened: Nat 20. Dm's ruling: "You lost your grip on your sword, inadvertently flinging it straight into the chest of that pirate over there." Perception check to WAKE THE FUCK UP. (Party was in combat.) Nat one. My Tiefling Wizard slept through the entire combat, and my best friend's character drew on his face as punishment. Then there was the low roll to preach to a tavern full of elves (it was an elf bar) that got the Teifling and the Paladin kicked out of said elf bar. (It was the Paladin who was trying to preach. My wizard was only with him.) Roll to make a fake horse look convincing to lure a, what was it, a wyvern or something?, into attacking so we could kill it without hunting down it's lair. We did NOT succeed, but the attempt was hilarious. Roll to seduce dragon: nat 20. Dragon's roll to resist seduction: nat 1. Dm's ruling: The dragon falls completely in love with the bard, proposing marriage and changing his alignment so he can be with her. (Unbeknownst to the party, including the bard herself, the Bard who did this was at that very moment already pregnant with an incubus' child. So THAT was an interesting family.) There might be more, but this is what I can remember.

I once rolled to throw a piece of bacon at another party member, not sure why I did, but I did... and I got a nat 20 which was especially hilarious considering the character that threw the piece of bacon is notorious for missing their shots in our campaign, like one time we had an entire fight and he didn't hit a single shot, luckily it was my side kick so I still dealt some damage. So the rest of the session was full of jokes like "Just pretend the arrow is a piece of bacon" and what not, good fun.

I the DM was running a mystery tower campaign and had the party so scared they were afraid to touch anything thinking something strange would happen. Well the ranger found a pot of soup still hanging over the fire. As she approached, she asked to roll a nature check on it. Natural 1. I told her it's a pot of tomato soup. For the rest of the campaign the party would ask her to roll a soup check to see if something was real or not.

My first ever session; It was a oneshot and my friend and I were playing as the same character(s). Very chaotic. We broke into a mansion and found the dining room. The kitchen next to it was full of fresh food; Most likely a meal prepared for maybe 20 people or more. Our character(s), conjoined dwarf twins, ate all of it. After a small discussion, our wish to roll for how much our stomach would grow was approved. Rolled a nat 20 If I remember correctly, the DM just gave us +1 constitution for that. Good times.

One of my fellow players called his crossbow his 'long range poker'. I jokingly stated he only thought it was that long. So the DM had him roll to determine the length of his... personal poker. Long story short we had a 4' 9" halfling rouge with a 6' 5" personal poker. We determined he had a small bag of holding sewn to the front of his pants to hold it. So far it was the oddest roll I've seen.

My gave Cyberpunk RED Tech a crippling fear of heights. We had finished a fight on a skyscraper and were about to be extracted via the heliport before more security arrived. My character was reluctant to board the heli but seeing as he did not have a parachute off we went. I myself decided to roll Resist Torture/Drugs and got a crit fail. My Tech got sick from fear. At the end of the session we were all given a small title to remember the mission or gig by and I suggested and got the title "Carpet Bomber"

For our current quest our party was task with tracking down a missing dwarf who was known for prospecting in the local mines. Our party finds the mines but has to do battle with a creature that is guarding the entrance and preventing the dwarf from escaping/leaving. We do battle with the monster and after 2 rounds of missing to hit due to terrible roles I singlehandedly do more that 50% of the creature's damage killing it outright due to a sneak attack crit. Well anyway we rescue the dwarf and get him back to the local tavern safe and well. I start to RP telling the story to the tavern goers over drinks and the DM has me roll performance for how well I capture my audience. Nat 1 (with a -1 con score for a total of 0). So I tell the story of how well we destroyed this creature and I even have a trophy from the corpse, but nobody in the tavern will believe me. That is the story of how I crit succeeded and crit failed in one table session.

Opening a door with a key Nat 20. Lighting a candle ... Nat 20 Eating with a Spork... Nat 1...

I told this story on another video but here is an add on to it as it was incredibly funny: It actually happened on my current (and first) campaign. I am playing a half-orc monk and at the time i was only level three. My party was planning an elaborate heist into a building with many soldiers to try and prevent this scary dragonborn dude from getting an overpowered item. Out of nowhere, my dumbass just says 'I run right into the hall shouting and gaining as much protection as I can.' Now this may have been incredibly stupid, but it was also useful. The party's elven archer managed to sneak into the building as all the attention was on me (this doesn't go anywhere relevant to this story though). After being seen by 15 or so soldiers, and knowing that i would not win, I instantly turn around and run through the city trying to find a place to hide. I broke into many houses, one of which was an orphanage with 2 little girls. So there is a big 6 foot 7 half orc bleeding from the arrows fired at him, towering over 2 little girls playing with dolls. I run upstairs and jump out of a window into a nearby buildings balcony. That balcony was the room to an elderly woman- who was getting changed. I desperately explain myself to this nude old woman and trying to get her to let me stay. I try to push her (lightly) onto the bed so I could go hide somewhere in the house. The DM asks me to roll a strength check. NAT FUCKING ONE. In brutal detail, the DM tells me 'the nude, elderly woman musters up her strength from 84 years of living and kicks you square in the balls. She hits both of them and you fall off of the balcony and take 5 damage. Also, take 1 necrotic damage from seeing old, saggy titties' A giant half orc was just kicked in the balls by an old woman with her boobs out. This shit was so funny in the moment.

What's the bet that sponsored content you plugged has the leviathan and the behemoth being dinosaurs…, I kind of want to play it to help carry along the Armageddon for the bad guys. 2:15

Long but, the funniest/best/worst skill checks keep involving the same player in nearly every game we play. His Character is Romulus, a Half-Dragon Wizard trying to escape his tormented past and his family's infamous reputation. His father, is an unnaturally powerful ancient Ice-Dragon that has destroyed half of the realm. So naturally, Romulus tries to keep a low profile and covers himself at all times. Unfortunately for Romulus, his compulsion to help others, and his success/fail combinations with skill checks, is starting to gain him confidence and attention. For some reason the dice gods smile on Romulus when ever he casts Prestidigitation. 1. The party is fleeing capture by walking through the Forrest at night. The party who are a bit unnerved due to past events, stop all of a sudden when hear something whispering in the dark in front of them; "hhhhaaalp mmeeeee, cccrrrhelp." What they don't know yet is a giant spider is attempting to mimic common, and trying to lure the party into its it's lair. The party rolls perception well, take up arms and defeat the spider. It is late at night and the party wants to rest in the spiders lair for "safety." As the DM I ask them the age old question, "are you sure you want to do this?" Romulus says "its okay, I will cast Prestidigitation in the lair to make sure all the creepy crawlies stay away!" Amused, I say "Okay, this will be a pretty high DC, so give me a strait roll and lets see what happens." The table laughs when they see that Romulus Crits on his roll. Me respecting it I say "Okay, here is what happens, you accidently have created DDT, nothing in the cave nor anything near the cave is crawling anymore. You remember all those crickets you hear chirping? The night is filled with nothing but silence now." 2. The party successfully defends a small town from a party of evil paladins. However, at the end of the battle many townsfolk were slain, and many of the buildings were damaged or destroyed. This includes the towns only tavern "The peoples Potato: Ale and porn, never corn" Romulus seeing how depressed and sad the townsfolk are, even after victory, wants to help cheer them up. "I want to cast Prestidigitation to see if I can clean up their tavern a bit." I say, "Okay, you can do that, I am giving you advantage, so give me a strait roll with another dice added." The result? Double Crit! The table screams with laughter and starts clapping. Me shocked; "okay haha, here is what happens, you really put your heart and soul into this cast. All of your emotions, the memories, the pain, and the joy of your past you put into it! What you do is repair all of the furniture, patch all of the burned wooden beams, repair the broken tables and walls, and fix all of the mugs and dishes." The town overjoyed at this gift throws a massive celebration. The party's mugs never reach empty this night. They are treated like kings. Romulus's can barely get past the foam layer before his mug is filled again. 3. But with success comes attention. The next morning there is a flyer outside of the Peoples potato regarding the next town fair! "Potato sculpture contest! Whoever can grow or make a potato sculpture look the most like Romulus wins the prize! Additionally there is a bard outside singing about "Sir Romulus" to a group of children. Romulus embarrassed at the attention, and worried about what might come from it pulled his cloak tight and creeps out of town. As the DM, I wasn't going to make it that easy to escape his reputation. 4. The next session, in a new city, the party is walking to its capital. its early evening. On the way there they walk past packed outdoor beer garden with a stage. There they hear the crowd clap and cheer as a bard walks out on the stage there wearing a crude ice dragon mask. The party all ready starts to laugh as Romulus sighs. "what fresh hell is this, is that me?!" The bard starts singing a new song. "The hymn of Sir Romulu, the Mend-Mage!" The player who plays Romulus actually gets embarrassed as I sing the song. "I am sir Romulu, the mage of mending. When things blow apart, I fix, magical blending. I defeated tyranny at Boulder Hill. My magic is deadly, evil I will kill. I am strong, I am beautiful, the ladies I love. I drink ale like a fish, and I pray to the gods above! Romulu, Romulu, the mage of mending! Adventuring forever, with out and ending!" The party mocks Romulus endlessly. so much so that Romulus gets needs to defend his pride and declares "ill bet you all 10 gold that I can sneak into the beer garden, buy a pint and not be recognized! so I ask him to give me a stealth check. Critical fail ! He collides into a beer server, trips and falls, drops his hood off his head, and reveals himself to everyone. The crowd goes wild "ITS THE MAGE OF MENDING?! Is it really him?!" Romulus tries to tell them that it isn't him. so I ask for a charisma check. Critical fail ! The whole table is dead with laughter. As the dm I say "okay haha, so this is what happens, everyone knows you are the Mage of Mending, everyone wants to buy you a drink. the crowd will not let you leave until morning." "this means that you can not get get a long rest, please give yourself a point of exhaustion." "Finally, please add a new long term project on your character sheet, 20 slots, named: Mage of Mending!"

9:00 - roll to see if you can detect the taste of a liar, GIORNO GIOVANNA!

Our Assassin Rogue was having us disguise up for a military assault on the BBEG nation. When I made a comment about wanting to look fancier, our DM agreed to have the Assassin roll for cosmetology. Nat 20. Apparently a disguise kit also doubles as a portable hair, makeup and mani-pedi kit.

Me and my party members rolled perception to discern the eye colour of a divination wizard ... who was reading our minds as a part of an interrogation.

One for an entire race. We have a homebrew race known as the Cicu ("HOI!"), which are small cactusfolk with a universal case of ADHD and the coherency of thought associated with Florida Man memes. So, every once in a while, they need to "roll Wisdom against Cicu-ness", or they do something like swan-diving into a puddle, getting distracted by a cat, chugging two entire jugs of mead with all the negative results, or trying to keep people warm by lighting the market square on fire.

This one has happened a few times in our campaign: Roll to see how beautiful someone is. Since beauty is in the eye of the beholder (pun intended), whenever one of my PCs asks how attracted they are to a certain person, I have them roll 1d10. Essentially scoring the person in question out of 10. The first time was after their main quest giver (a man) used disguise self to change into a woman to travel incognito with the party. 9. The next time, a PC used a homebrew cantrip to see through walls in a hotel, spying a woman getting dressed. 3.

This was a one-shot with only 2 players, and it had 3 such moments. My Rune Knight Fairy, and a Ranger. The Ranger’s race will be important later. We were to rescue a guild leader, and the thieves guild was our primary suspect. My digital dice had inherited Wil Wheaton’s dice curse. I couldn’t roll above a 5 even to save my life, unless I had advantage. So I couldn’t hit anything with a rapier, but I could grapple them. Our first encounter, we were stalked by a member of the Thieves Guild. Even with advantage from my mastiff mount, I got a Nat1. Luckily, the Ranger spotted the tail, and we set up an ambush in a narrow ally. We rolled initiative, and I went last and couldn’t hit the thief. The Ranger then cast Spike Growth. I remembered the grappling advantage, and that I had wings; I cheese gratered that thief into the single digits, then finished the interrogation. The thief gave up a potential hiding spot across the river. As the DM described the wharf, the Ranger decided to seek a captain at an adjoining bar. I cited the “heavy smoke” as a reason my rural Fairy doesn’t go in. (In reality, I dominated the interrogation, and wanted the Ranger to have his chance at roleplay). The Ranger went in, failed a persuasion roll, and started a bar fight with 2 drunk sailors. Again, I moved last in initiative. The DM gave me seeing the fight for free. I went over my options, and realized I had nothing helpful for a bar full of more sailors. Except for one thing I had Advantage in. “I use my object interaction to tuck my wings into my cloak, trying to make myself look as much like an elven child as possible. I then run up to the Ranger, tug on his coat, and say ‘daddy, you pwomised me a wide for my birffdaaaaaay!’ I am using my full Action on Deception.” Both the Ranger and DM laughed. Then the DM realized something, “you want to convince these sailors that you’re an *autognome’s* daughter?!” “Adopted daughter!” More laughs, I roll. 19! The sailors are so drunk, they don’t question it. They smile at the birthday girl, and recommend a friendly captain. When we got to the hideout, I rode in on my mastiff. The DM asked me to roll a D20. Immediately, a goblin inside the front door hits me with his dagger. I roll to hit, with advantage: 26. The rapier passes through harmlessly. Out of character: I recognize Phantasmal Force. But I played it off like I didn’t get why the Goblin didn’t move to chase after me as I rescued the guild leader. He was in an adjacent room, tied up, with the kidnapper standing over him. I cast Enlarge on my mastiff so he could carry the human guildmaster, and Action Surged an attack that OHKO the attacker. But then, Silent spells began targeting me and my floofer. We rushed to the opposite end of the small hideout, away from that room, while the Ranger handled the two big goons. Myself and my floofer then had to make Con saves, and on a fail got knocked prone 10’ away. The guildmaster was unaffected. I immediately turned to the DM. “This is not meta gaming. My fairy is multiclass Warlock, and she has Thunderwave on her spell list. She turns to the guildmaster and shouts ‘deceiver!’ I attack him.” He cast invisibility to run away. I return to the first room, saying “Ranger, keep those goons pinned. You goblin, keep standing there uselessly,” gave the ‘captor’ a Potion of Healing, and said “sorry sir, you still look like the captor to me.”

In the very beginning of my homebrew campaign (I was DMing for the first time) the party sat in a tavern full of dwarven soldiers. The party was helping the dwarves to defend their land during a war of aggression by neighbouring state. One of the party members had a background in the dwarven army. He rolled to see if he knew the soldiers at the next table. Rolled a nat 1. "You don't recognise any faces. The emblem, though, haunts your mind as the soldiers start turning their heads towards you. It is of a regiment rivalling yours. They hate your unit's guts since they wrongfully blame you for a major defeat they suffered recently, encurring a lot of casualties. Roll for deception." Of course, another nat 1. Roll for initiative, I guess. Our artificer and cleric were shitfaced and our Barbarian played a horndog and seduced one of the waitresses, leaving the rogue on his own...

“Macrocapitalist aberration” sounds like an expansion enemy in Cyberpunk

This was a campaign where we were all dogs with human-level intelligence who wanted to become humans. We had to find the various dog-gods and convince them to work together to power a machine strong enough to permanently polymorph us into humans. I messed up an acrobatics check to avoid falling off a wall. I was already dead from the height, so I asked the DM if I could roll to see how hard I "screwed the pooch." I roll a nat 20. A pooch god named Waggy literally materialized from the Astral plane to have mid-fall intercourse with my character. This was the end of Bagel the Beagle. Died doing what he loved most; bitches. Later in the campaign, it was revealed that Waggy had given birth to Bagel's pups. One of them was named "Cream Cheese" in my honor.

probably that time my introductory cleric (to help new players) punched a wall (Nat 20) to escape a prison area basically atomized himself

We’re currently playing Forgotten Realms. It’s my first campaign I’ve ever been able to take part in and I’m excited because I’ve had this character ready for FOUR YEARS. Half-Elf Ranger with proficiency in medicine and survival, among five others (mostly useless, don’t worry) because I rightfully convinced the DM through my character’s backstory. Anyway we were level 2 and were in the Greenest keep when a blue dragon showed up. Mid-fight, I was behind a pile of rubble for cover. Well the dragon absolutely pulverized that rubble pile leaving me completely exposed. I looked to the DM and said “uhh…I’d like to roll not to shit my pants…”. Nat 3. Pants: shidded. Edit to add: I don’t know WHY Forgotten Realms has a DRAGON ENCOUNTER at LEVEL 2. Makes no sense to me as it would physically end our characters’ lives permanently, no death saves.

8:49 This taste... is the taste of someone who's lying, Giorno Giovanna!

I roll for depression sleep. I don’t remember the roll but the SCP reality warper I was playing woke up on the beach very confused after our cruise ship crewed by ants exploded.

Random seduction and one diplomacy both nat 20s lol

My goblin artificer runs into a tent to hide from cultists chasing us. I jumped into a bag to hide. It was a bag of laundry. Dirty laundry. Had to make a Con save to not vomit and blow my cover.

My first ever time DMing, one of the players made a remark along the lines of "He has small dick energy" referring to one of the NPCs. I rolled a D20 and said, "Actually, he had average dick energy."

I remember this due to the bad luck my party member had, was being guided through a sewer by a little girl and my 1 party member, who was in full plate, first rolled a Nat 1 on dex save for if anyone slipped in the sewer everyone else passed the check. And he did not just fail the check once, apparently the little girl was just leading us in a circle and he kept slipped over and over again in the same spot. Only for the rest of the party to realize we were going in circles. Was revealed the little girl to be a adult white dragon and just kept us going in circles because they found enjoyment in our one party member slipping in the same spot.

We keep an informal board of funny things that happened, I grabbed a couple that were check-related: Player:: I will sneak by the fire. (Nat 20) DM: The abandoned mundane completely normal campfire does not notice you _____ Player: What do I roll to chuck this flaming potato at the tiger's stupid face? _____ Player: My Copper Dragonborn resists acid, can I have advantage against being digested? _____ Player: I want to fire Magic Missile point blank into his eye sockets by first jumping over the table, then grappling him into a headlock. DM: Um... Magic Missile doesn't... miss? Player: JUST TELL ME WHAT CHECKS MY WIZARD NEEDS TO CAST KUNG FU! _____ Player: Does my pet goat get a chance to perform for the Volcano Temple door? _____ DM: (sigh) I did not expect you to step through that portal, roll a religion check to keep your soul in your body.

Rolled a grapple check on a fricken leviathan! Somehow it worked. I was just holding onto its neck for dear life and caused it to waste actions trying to shake me off.

Tame, but my group still laughs about it. Early into Dragon Heist; wizard is out of cover, decided to leap over the bar to get cover. Nat 1. Me, as DM, "Well.. hmm.. Okay, so, it uses all your movement." Wizard, "That's fair." Me, continuing, "You do make it over the bar. But instead of the heroic leap, you fall flat on your belly, and just kind of slide across the bar with a fight disrupting squeek before flopping over the other side like a cold fish. You are prone. After a long pause of everyone, including the troll and these mosquito things I keep forgetting the name of, the combat resumes." Everyone laughing their butts off.

i played a goblin bard who had a bag pipe so i started swinging in a sword while playing them to piss off the spiders D.M: roll for performance check "nat 20 "somehow you swing in to battle blasting your bagpipe"

the first story has the most subtle shit ever

Would love to know more about the last story.

"Roll for Titties." The Kitsune Bard wanted to distract some newbie bandits trying to rob the party by flashing them. Most of them were killed, but the survivors suddenly became furries. "Roll to Forcefeed Illithid Painkillers." We burned out 2/3 of Strahd's Legendary Resistances, so my Dragonborn Fighter had the idea to dump some pills down his throat to make him OD. All 3 of his resistances were used up and we proceeded to blind him and beat him as a blind mist via Sentinel. "Roll for Out-Of-Character Future." The party at the beginning of my one-shot didn't know what tavern they were accused of burning down. After one succeeded, I told them it was a medieval Dairy Queen, and they understood why it was worth the death penalty.

There was a door that had three locks Lock one nat 20 Lock two nat 20 Lock three nat 4 Locks reset Lock one nat 20 Lock two nat 18 I think Lock three nat 1 Locks reset last try Nat 20 I think nat 17 Nat 20 We were absolutely loosing it the whole time

Playing a more modern-time game. Anyways, one of the NPC’s falls into a coma. We all decided unanimously, t fart all at once. We rolled over like 50 collectively (there were 6 of us) and so, by collectively combining all pf our farts, we forced the comatose person awake through sheer stankage. On another note I rolled a nat 20 on yet another fart, causing a small earthquake, but this time, it made corpse-worms eat one of the party members alive, so that was fun.

party consisting of a sorcerer (fairy), rogue (half elf), barbarian (hafling), and cleric (Human): sorcerer (me) and cleric got separated from the barbarian and rogue while falling into a cave. Barbarian and Rogue come across a mirror which they determined to be a secret doorway out of the cave. their reflections had minds of their own and mocked the 2 PC's until the barbarians reflection started holding a shiny rock like it was a baby. The Barbarian found the exact rock in the cave. because neither knew magic they tried doing multiple things to it like throwing it, smashing it to no avail. At one point the barbarian goes "i shove the shinny rock the rogues ass".the DM says"fuck it roll". Natural 20. We spent a good 15 minutes laughing on the floor.

Running gag in our campaigns. Whenever a hot woman shows up, the men roll a CON save to not get an anime nosebleed.

Revelation the D&d game sounds pretty dang wild. Sign me up!

I would like to hear the update on the last story that you have on this video.

We were going through the Dungeon of the Mad Mage and came across a wererat. Knowing that she had information about the dungeon, we attacked her with non lethal damage. She then proceeded to beat the shit out of our Goliath fighter. When it came time for our Barbarian Aspercreme to go he looks at our DM right in the eye and says “I need to do non lethal damage right? Okay, I pee on her!” We lost it. Our DM had to walk away for five minutes to just process the action. When he came back, a little more dead inside he just sighed and said “Roll for dexterity to see how well you aim I guess.” He got a 4 and proceeded to pee on everyone but the target.

magnetic belt buckler, metal zipper. and you have to pee. Roll for *Dexterity*

My player rolled to fart. He failed, and pooped his pants.

Last story had a very happy ending :)

That lucky barmaid.

My second campaign began with the party riding on the back of a dragon. I asked the DM if I could roll a CON save against airsickness, which he agreed to. I proceeded to roll the first roll of the campaign, a nat 20. We all laughed our asses off and proceeded as if nothing had happened, because indeed, nothing had happened.

I remember having a roll for D size using a D100

9:01 So a Lizardfolk version of Bruno Bucciarati? Please tell me they dropped the whole, "I know this taste. It is the taste of a liar," line, please

Ok, I felt that last one since one of my most beloved characters ended up with kids *older than him* (some by centuries) due to time travel shenanigans.

So as it turns out the spell illusion can stack. I found this out because I just keep casting it on an enemy and broke there mind

But what was the present for the one DM after the first session?! Episode, type of question was asked (i.e. What are your most epic fails in DnD?) etc. I NEED TO KNOW!

3:07 Uhh, DM, Max Damage would want to drop the spell because the spell IS LITERALLY KILLING HIM! Edit: Oh if you're playing him dumb then I withdraw my statement.

Roll pro Forman e so you don’t kill her. I was playing a centaur and the party was in a brothel to meet with a contact of ours. However only one woman was brave enough to proposition a centaur. I accepted and the DM said “ok she’s just a human so roll performance so you don’t kill her.” I rolled a 14 and she was knocked out but lived. She did get pregnant and I stuck with her dispute her giving me a out. Now my PC is married to her and we have 3 kids and another on the way.

I once managed to resurrect an ally who got decapitated through divine intervention. I was way too low level to actually cast any of the actual resurrection spells, so I decided to try my luck with the Mending cantrip instead. Since it was a one-shot and because my character was basically Tortle-Jesus the DM let me roll a Religion check and I got a lucky 20, so they ruled that my chosen deity had stepped in and "Mended" my friend's head back on.

The only one I can think of was how another PC came into the campaign after theirs died earlier in the session/end of last session. They tried to intimidate us during their introduction, so I immediately said, "I counter intimidate!" I don't remember the exact rolls, but it ended with mine being higher at or above nat18, so... ya

i failed multiple times to open an unlocked door, the dm did not make me roll, it was entirely my own decision

I rolled a 7 on a skill check to put a gold coin in the pocket of the tavern keeper. I failed the check and I got the gold coin back. Ignore later that session I stole some potatoes from the same tavern.

Just last session. My character was trying to recover the ashes of his mother who had died in hopes of using a Reincarnate scroll on her. The Druid in our group thought it’d be funny to, as an air elemental, swoop by and scoop up some of the ashes via teabaging. At the end of the fight he offered the ashes to me but stated I should roll to ‘fondle’ my hand into the lower half of the elemental to recover them. The dm agreed.. I plan to resurrect my characters mother next session.

8:49 Didn't Bruno basically do that to Giorno at the beginning of Golden Wind?

thats isnt how flame sphere works, that much water instantly kills the spell and it wouldn't give off enough heat to cause water to instantly vaporize like that. that DM just wanted to make any excuse to get more damage on the players

Tell us more about said scaly bounty hunter please!!!🥺

DM:"Fine. Roll persuasion to turn him into a communist." Me:"Nat 20" DM: "... fine... he burst out and starts singing the soviet anthem" Bard: "Wait the soviet union exists in this game?" DM: "What? No, bu-" Paladin: "STALIN IS CANNON!!"

I rolled 3 nat 20s in a row for "drinking"

8:03 yay my dumbass story is in the video lmao.

I got a nat 20 to do paperwork for a lazey governor

Funniest for the table not for the GM(me). Someone asked to make a cooking check to smoke the severed heads of the enemies they killed so they could get reward money. The only time I've had to leave the table to gather myself.

I did once play a character who successfully seduced a drow woman at a party. The DM had me make a few constitution saves, and took a little damage as they hooked up. By the end of it she was doing that Maude Lebowski knees up to encourage fertilization thing, telling me "If it's a boy you can keep it" She's not my special lady, she's my fucking drow friend I'm just helping her conceive.

I mean, it isn't a funny skill check, but it was hilarious that my wizard rolled 5 n under on every int check the last 3 sessions. *Tries to read scroll* "what the fuck is a scroll?"

This just happened earlier today in session 1 of dragonlance. The party is traveling through a forest and the kender rouge thought it would be a good idea to throw a rock at the half orc barbarian. Nat 20. Obviously the half orc was quite mad and responded by trying to intimidate the rouge. Half orc rolled a nat 20 for a total of 23 intimidate and the rouge rolled a natural 1 on their wis save. So the rouge ended up soiling themselfs and is now very afraid of the half orc for a long time. Later in the session the aracocra sorcerer thought it would be funny to piss on the wood elf ranger. Ranger failed the dex save miserably.

_Hearing that a player had to roll to commit tax fraud_ Funny as that is, the real question is…did they succeed in the roll?

So Many sex jokes in one video player make the questionable decision leading to dm having to fade to black.

I'm hungry