Hilarious Roleplaying Stories

Hello everyone on the Boards!

Be it at home, online, with friends, or with strangers, many have engaged in the experience of interactive story telling that we call roleplaying games! Now, these games are usually meant to be grand tales of adventure and heroism and success, but even the best made plans of mice and men can go awry!

Ever have a moment while playing a roleplaying game where something off the walls funny happens? Maybe your group was about to raid a dungeon when suddenly a player trips and falls to the ground? Perhaps someone is giving a dramatic speech and says something awkward? Maybe a friend attempted a ridiculous course of action and it ended up working, or failing hard? Share those moments here!

I have plenty to offer, as my campaign with my friends often goes wrong.

One session, my party was investigating a halfling village known as Silverhills for traces of a corrupt paladin known as the Oathbreaker who was terrorizing the land. My group, however, included a paladin, and the mere sight of him invoked hostility from the village guards.

Taking him to be the Oathbreaker, the paladin of our group, named Adolamin, was captured and jailed after failing to fight his way through halfling guards or convince them he wasn’t the rogue paladin. Now, I forget exactly how, but somehow my character managed to get captured and jailed as well. In adjacent cells, Adolamin and my character, Ghar, attempted to break out to inform the village leader, Leonna, who was married to our party’s halfling bard Roscoe, that we were innocent. As bad a plan as this was, it managed to get even worse.

We used a spell to escape our cells and managed to make it outside the jail, but my paladin friend decided to summon his magical steed construct to skip town. The horse, who was sentient and could talk, was so freaked out by the guards and the chaos of us running that he completely ran over numerous halflings. After our paladin mounted the horse, he told it to run away, where it again murdered more innocent halflings in its wake, confused out of its mind. When faced with how to get over a dying halfling, Adolamin urged the horse to jump.

Now unfortunately, I had not seen the horse as I exited the jail, and was clotheslined as I was sprinting away. On the ground now, I couldn’t move because of the impact, and loe and behold here is this horse above me, ready to jump.

Guess where it landed? On me.

My shins, shoulder, and stomach became mashed potatoes and I nearly died as I screamed “NOO!” for the horse not to jump.

A battle between our party and halfling guards ensued before it was eventually ended by Roscoe and Leonna, where we then spent months in intensive care.

But at least I have some awesome metal shins and shoulder now!

Have any stories of your own to share? Maybe not even directly RPG games, maybe just funny things that happened between friends while playing some kind of game? I’d love to hear!

As always,
Comment and Enjoy!


There we were:

It was the dead of night aboard Refuge Station (The station has artificial lighting based on current time).

We walked into a shady part of the station looking for our contact.

We entered a small set of hallways.

There we saw him.

The Orcish Knife dealer named Edge had an eccentric look about him with a very large coat and Mohawk.

As we approached he looked both ways to check if anyone else was in the hall.

Then in the lowest of whispers he says: “Got something special for you today”

he pulls a poorly packaged object out of his coat and hands it to the party leader.

After we were back in a safe place we opened the package to find what we wanted inside:

A box of illegal memes.

(needless to say that wasn’t a very serious campaign)


Our rouge thought it was a good idea to go investigate the bandit’s tavern outside of town all by himself. Needless to say he was discovered and next thing you know we have twenty-nine angry banits outside our tavern screaming that if we don’t hand him over they’ll burn the place down. Our barbarian, who was somehow the designated spokesperson of our group up till then, and one of our paladins approach to threaten them while our ranger found a sniping position on the roof.

Now it is at this point I should mention that we have a Warwick and a second paladin, however they were unavailable due to being asleep (both in game and irl, nap checks are a thing in our campaign). It should also be noted that I was playing a brand new character because I had gotten tired of my murder monk (punching things gets old) and while my previous character had God stats, my shiny new bard is much less sturdy. Needless to say, i was not liking the 29:5 odds.

It is at this point that I stroll out of the tavern, mind you, this character is so new he’s not even really a member of the party yet, as far as they’re concerned he’s just some dude. So I walk up to the horde of bandits, and momentarily try to talk them out of burning the tavern down. They take one look at me and decide I’m not worth their time. So, really not wanting to get into a fight, as I was already a little low on spells from healing the rouge, I yell “Hey look there they go!” And minor illusion our rouge ducking down an alleyway across the square, this of course led to a deception check.

Now it should also be noted that I did not roll very high. I rolled a natural 10. But being a bard I have a +9 to deception, so it worked out.

All but one of the bandits file out of the square down the alleyway I pointed. The remaining bandit walks up and politely asks if he can please have a look inside just to shut them up if they don’t find the rouge. I say sure and lead him into the tavern. Luckily our rouge was waiting just inside the door to sneak attack in case of a fight, so as I walk in i reach out towards the side and cast invisibility on him. The bandit looked around, found nothing, apologized, and then left. No blood was spilled that day.


The Self-Moc Actual Roleplay’s. All of them.


I am part of a Group of people that have had an ongoing bionicle rp on KiK for almost a year and a half. and even Before that we had Another one that got rebooted into Another one that got rebooted into the current one we have today. all together we´ve rp´d for almost 4 years. usually we´re just a Group of overpowered unfunny edgelords but sometimes something magical happens.

so after we defeated yet Another one of my very overpowered villains i decided to introduce my selfmoc into the universe. I decided to make him an omnipotent god from Another dimension. so what did i use this powerful character for? i decided to troll my own characters. i remember that one of the first things i did was turn my anti hero character into an evil wizzard against his will.(we allow multiple characters to be played at the same time. I´ve Always got around 5 or more at a time to keep track of) and then having him capture a rabbit princess. then some time later Another player introduced a god character of his own. his being a tank driver with a german accent.

It was in Halo: Into the Howling Dark Definitive Edition, post 1000ish. @RaptorTalon had decided to kill one of the post bosses, naming him Dipperman as a typo.

After the battle, where he brutally kills Dipperman, we began hailing Dipperman as a noble soldier that had been wrapped up in something he didn’t understand. Then the joke escalated and now we’ve made him the God of Howling Dark, where he’s now ex machinaing people left and right in post 9000 ish.

Then there was the original Howling Dark, @EvilLobsterKing had broken a radio, and was trying to fix it before the RP died.


Dipperman was never a typo tho…I just created a god, simple as that


Prepare, for the “hilarious” RP story that happened when Distraxx was 10…

It was an usual day in Animal Jam, playing games, doing stuff. I had recently gotten a Snow Leopard, so I decided to roleplay in the “RP Central”. I liked Warriors at the time, so I was an (terrible) OC of mine, Deathtail. (Yes, that’s what he was called. It was complete cringe.) I went to the forest in the most popular world and the hilarity began. I went down the slide and started roleplaying. I started looking for a clan, but it was taking longer than expected. So I hunted instead. About half an hour of doing random stuff I finally found a clan and joined. It was cringey as you could imagine. I roleplayed for about two hours, and then the leader said, “LightClan is attacking us, we have to prepare.” We prepared and then the war began. We fought, and this was it: “skills with light power” “skills with dark power” “uses sword” “claws” “ends no nothing no miss”

Somehow DarkClan (That’s what it was called.) won. And then I quit Animal Jam two years later.

The end.

This was the second session of @Scorpion_Strike’s Legends of Karzona RP.

After successfully fending off an attack of shark people on their ship, the Fellowship of the Wrong disembarked at the port town and began entering it to seek information for their own purposes. It ended in a contest between a dwarf rogue and a warrior monk versus an elf wizard, a warlock, and a paladin over a fisherman’s boat with the former party trying to steal it.

It ended with our dragon born attempting to charm a lady of the town and critical failing his charisma role.


Happened in “The Powers That Be,” @Katuko’s Lost Chronicles campaign.

For reference, this is my character in that campaign:

Insert dark, ominous and edgy soundtrack here

A couple sessions ago, having traveled across an island where some shady things are going down (surprise surprise), we found ourselves in a Fe-Matoran fortress but at the foot of and partially carved into a very steep mountainside. Being Toa, our team entered the fortress from the steep mountainside without much trouble, only to be informed that an army of Skakdi, grouped across several camps, were preparing to assault the fortress from the desert to the west. Spotting the similarity of the location and circumstances of our arrival with a famous fantasy location, our first order of business was to name the fortress “Mask’s Deep.” Having named the fortress and established that its ruling Turaga was the most buff Turaga in existence (yes, he does lift, bro), we set about preparing for the events to come.

Kruhdak, our Toa of Magnetism, resident engineer, subject of hundreds of “Kruhdak engineering” memes that liken his work to the products of the Roadrunner cartoons’ ACME corporation in both variety and quality and owner of a pet bohrok imaginatively named “Bastion,” decided to spend the time rigging up exo-toa suits to aid in the battle.

Kuan, a Toa of Fire who’s ostensibly our leader and a true Mask of Speed junkie, got a weapon upgrade.

Orion, our second Toa of Fire with what I can only describe as a fetish for collecting and painting pets (most notably the now positively suicidal Gafna Jenkins, who he painted candy red), brewed up some poisons.

Much scheming between them and the other members of the team concerning the neutralization and possible recruitment of one Skakdi camp’s Tahtorak mounts also occurred.

And then there was my character, Mestrelis: a Toa of Shadow, basically a natural rogue but equiped with a massive two-handed scythe and, ironically, a Midak Skyblaster. That night, Mestrelis took three willing Matoran with her into the desert on a mission to scout out and possibly engage in some sabotage or distraction to affect the Skakdi’s… effectiveness in the battle to come. We headed to a camp in the southwest: the gunners’ camp. The gunner Skakdi had brought all manner of dangerous weaponry to their side, including an assault vehicle and a lot of ammunition that the Matoran in Mask’s deep were coincidentally running short on. Recognizing the opportunity to perform some valuable sabotage, Mestrelis and co. hatched a plan. Mestrelis would sneak around the camp and engage in some mischief with the Skakdi vehicle. If/when this started to attract attention, she’d use her Shadow powers to get away (shadow teleport is a thing, and it was night). The Matoran would keep watch.

As it turns out, sneaking up to the vehicle, which was parked at the edge of the camp to begin with, was pretty easy and sabotage commenced. Firstly, our intrepid Toa of Shadow poured a bunch of sand into the vehicle’s fuel tank. Finding that it had deployable legs as an alternative method of locomotion, she then cut the hydraulic lines leading to one of them. Lastly, a large jerry can’s worth of fuel was poured over the vehicle’s internals. All this attracted no attention from the Skakdi, who were just being bros around the fire until their boss showed up and told them to shut up. After sneaking out of the camp, Mestrelis got another idea: if these Skakdi were so unprepared and inattentive, perhaps our little raiding squad could make off with a much-needed ammunition crate. Thing is, the camp had two large crates and both were set up right next to the commander’s tent and the campfire. To get at them, we needed a distraction.

Some meeting with the Matoran and taking of brave pills commenced, after which the Matoran set up east of the camp, as close as they could get without being seen. Mestrelis headed around west again, taking with her one of the Matoran’s weapons: a fireworks pistol. Recall that the insides of this vehicle were already covered in gasoline. One shot of the fireworks pistol later, they were also on fire. This of course got the Skakdi’s attention, who mobilized anyone and everyone not drunk off their minds to fight the fire and to chase the culprit (i.e. me) into the sand dunes. Predictably, chasing a Toa of Shadows into the shadows of the night led them on a long trail to nowhere, and Mestrelis was able to sneak around the camp and meet up with the Matoran, who promptly displayed the power of three disk launchers by dispatching the one Skakdi that noticed and came after them and the crate with a concerted volley of disks to his face. Too bad they weren’t powered disks…

Either way, while the Matoran got out with an ammo crate and the Skakdi were still busy combing the desert to the east and putting out the vehicle fire (which by this point had thoroughly wrecked the vehicle), Mestrelis got another idea: generally, ammo crates do not react well to being shot at, and the fireworks pistol still had some shots in it. Unfortunately, her marksmanship is less than stellar (more of a hit-and-run melee build) and both fireworks shots were wasted and attracted the attention of the Skakdi. I still had the Midak Skyblaster, of course, but at night it didn’t have much ammo to work with and I was running out of time before I had to get out of there. Still, fingers crossed, Mestrelis took one more shot at the crate with the skyblaster.

It hit.

The resulting explosion was monumental, injuring a bunch of Skakdi, setting fire to everything that wasn’t already soaked in water from their firefighting efforts concerning the vehicle, and dispatching of many of their weapons and ammunition. When, over two sessions several weeks later, we finally played out the Skakdi assault on Masks’ Deep, the gunner group showed up low on ammo and having to PUSH their assault vehicle through the sand to get it into position to even fire on anything, never mind contribute to the assault in any useful way. In all, the raiding proved a highly productive session.

Anyways, that wasn’t per se the funniest story to come out of that campaign so far (there are many, many more), but it was one of the most spectacular.


It was right there in front of me.

My greatest regret, my greatest failing in life…


(Note: I was not personally involved in this story, it was an adventure my brother was running for some friends using 2nd edition runequest in the fantasy world of Glorantha.)

The players: A beard and clothes hating bearwalker (werebear) barbarian (not the class), a griffin, and a jolly noble and his pet wyvern, a tiger son (weretiger).

What happened: Our players were in need of some money, so naturally they attempted to rob the blacksmith in the dead of night. Unfortunately, our griffin did not realise that he was to big to sneak and the load squawking awoke the blacksmith who goes out into his backyard to see a guy dressed in a bearskin loincloth and a griffin. The griffin attempts to give a warning peck, but his beak did to much damage, and the blacksmith’s arm fell off as he died from blood loss. The griffin swiftly took the body away, but forgot the arm so the next door neighbor comes out to see what in tarnation is going on and sees a barbaric figure standing over a pool of blood with a severed arm floating in it and yells: “CANNIBAL!” Luckily the rest of the party swoops in to pick him up and distract the guards with money, letting them make a clean getaway.

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We were playing 5e, and I’d designed a sort on intro module, for a few friends who’d never played before.

As they entered the town, complete with dwarfish garrison, the Dragonborn Warrior rolled a nat 1 for his history check, and mistook the dwarfs for very beardy halflings! Not only that, but the other PC then rolled a nat 1 to try and convince him that they were in fact dwarfs, and started to doubt it as well!

The best part of all this is, a few weeks later I was running the same module for some other people, and the same thing happened! :smiley:


I was DM, and after one of my player’s unfortunate low roles resulting in the loss of his hand, he decided to try and use a nearby magic circle to call upon the spirits of his dead slaves (long story) to fix his hand. I told him: “You need a 20 to succeed. You are a barbarian, you have no magic, so you need a 20.” He continued walking towards the circle. I reminded him that he would have almost no chance of success, and the campaign was nearly over. He tried anyway. He didn’t roll a 20, and I made an evil spirit appear and start draining his life. He freaked out in real life and began yelling profanity and trying to shoot me with a nerf gun.

Another time, I was a psychic sorcerer in savage worlds. We had been traversing through a pyramid filled with marbles and feathers (a temple of the god barble), and we had just come to yet another trap. At this point, I was tired of traps that made no sense, and said to my GM: WHY CAN’T WE JUST FIGHT SOMETHING? She got angry and spawned 10 skeletons. I slightly regretted my choice.


I’m back with another story!

Now, our campaign has had two iterations, our original campaign and our current, soft-rebooted campaign that takes place 2 years after the original. The story to why that happened is probably the most hilarious story I have, so I’ll save that for another time…

Well, the story I have now takes place fairly early on in my group’s original campaign, and it has become a meme in our group (as every funny thing has).

Our group was on a journey to find the location of a camp of necromancers that had been attacking the city of Luftaren. Our benefactor, a man named Evendur, had shown us that the way to the camp was a small forest path. After managing to pass a felled tree and cross a raging river with some difficulty (the tree alone took close to two sessions…we were new to D&D…), we came to a narrow path where we had to go single file.

Looking up, we noticed a large crow in the trees, just staring at us. One of our party members investigated the crow and we discovered it was a spy crow and that someone was watching us…

Now, we were planning on how to illusion and sneak our way past the crow when suddenly one of our players who was playing a neko (a cat-girl mix…don’t ask…) decided to climb up the tree and claw at the crow!

The crow, startled, started to fly off and make noise, but my character Ghar wasn’t about to take any of that! I aimed my hand crossbow to the sky and fired…

I rolled a natural 20, shooting the crow straight through the eye, killing it instantly!

From then on, my DM allowed me to insta-kill any crows or ravens I saw, up to two each time. I gave myself the custom ability I called “Crow’s Bane”.

To top it all off, my DM’s girlfriend, also a member of our party, got us all socks for Christmas this year. Guess what was on my socks? Crows.


Been playing a campaign with my pals for over a year, here’s a few of my favourite bits:

  • Going around houses, inconspicuously asking for information. My friend, the Yeti, decides to knock the door down and yell “HELLO WE ARE HEALTH INSPECTORS.”
  • Me and a friend went undercover as slaves to infiltrate a corrupt leadership. He does a long monologue about how he’s lived a painful slave life, whilst I yell “I AM A SLAVE.” He rolls a 5. I roll a 20. It does not end well for him.
  • Me and my friend Ben (The Yeti) get into tons of hijinks, the best of which being when he had to pose as a rich aristocrat and I reprised my role as a slave. In order to gain attention as a rich person, he goes, “BOY, FETCH ME A CREAM BUN!”
  • It’s worth noting that Ben’s Yeti character wears an array of aprons with different food puns on them, my favourite being “It takes Two to Mango!”
  • We enter the super originally named “Tugator”, a pirate’s sky port, where we meet the crime lord Shark Tooth after performing a heist for him. At this point not much has happened in a while, and quite a few of us are getting bored. What was SUPPOSED to happen was we were going to do some more heist work for Shark Tooth. But we may have started a bar-room brawl that burnt down a fair amount of the buildings.
  • We fly about on a sky ship called The Black Porpoise, captained by Holly Hart, aka my friend Tom. One time he wasn’t able to make it to the session. That was the time we fought a sky leviathan. The Black Porpoise didn’t make it. Tom was not happy.
  • My character is a monk, which involves a lot of jumping around and avoiding damage, leaving me with not much to do while the team rests. I have some cook’s utensils though, so I am now the chef who also saved the whole team from poison due to my cooking skills. Battle’s over and what’s everyone doing? People are healing, looting and calculating their next moves. I am… cooking a nice meal.

I’m currently chronicling the adventures of my team, too- so I can relive all the zany moments.


I don’t know why but I’m just imagining the chimichanga ogre from Shrek Ever After.

also your monk is like the polar opsite of my old mad tinkering murder monk character…


All of the Self-MOC RPs were a mess.
I remember when @Hutere had the idea for an island called “Tipukoto” - It was eventually renamed to Tregaron, but nobody, not even I, could predict how it would end eventually.

Basically, people lost the will to keep RPing in that terrible mess, everyone wanted Tregaron to die. - So I asked the DM, that being @DG_Eddie if I can introduce my massive undead army from another planet. - Yeah, weird… but nothing else could have saved Tregaron at that point.

Anyways, the grand climax ended with Hutere sending an exploding dragon, which was supposed to be Tregaron’s final fail-safe… yeah, an exploding dragon. - Let that sink in.


What are you talking about? That was the best part.


''Twas ridiculous. And all the while my character was just sitting on the ground watching the fireworks and wondering what the heck was going on.