D&D Boss Stories of Hilarious BBEG Takedowns

We’ve collected some of the most epic moments from DND campaigns of boss fights and hilarity.
[Image from Vecna: Eve of Ruin]

In the world of Dungeons & Dragons, bosses (a.k.a. BBEGs, Big Bad Evil Guys) are the grand finale of a campaign. After weeks of fighting their way to the top, the party is all leveled up and ready for an epic battle. Some of the best, most epic D&D stories are these boss battles, when the characters get to use their wildest spells and most powerful abilities. We’ve been running games at Young Dragonslayers for over five years now, and we’ve got the zaniest, most creative players in the world: tweens and teens! We’ve collected some of our favorite D&D BBEG stories to share, from fighting an anime vampire to playing darts with Vecna. 

This D&D BBEG Was Defeated Via Magic Ape Cannonball

This BBEG DND story comes from the world of Critical Role.
[Cover art from Call of the Netherdeep]

Dungeon Master Zach got to run an adventure called Call of the Netherdeep taking the party through strange underwater locales, mysterious ruins, and the intrigue-filled city of Ank’Harel. (This comes from the world of Critical Role, a beloved D&D podcast – albeit one we don’t recommend for young listeners). In the final boss battle with [REDACTED FOR SPOILERS], the party set aside swords and shields and instead turned to magic and creativity! The party warlock was a genie, who had the ability to shrink back into their ring, Aladdin’s-lamp style. They popped back inside, and the party wizard cast a spell to catapult the ring far above the boss’ head. Properly positioned, the genie popped out of the ring and immediately Polymorphed into a giant ape, cannonballing 90 feet straight down into the Big Bad’s head.

“Reader, I wept from joy” - Dungeon Master Zach

An Epic D&D Story of Teamwork and Vampires

The most epic DND stories come when the party does something no Dungeon Master would expect.
[Image from JoJo’s Bizarre Adventure]

In another campaign, the big boss was Dio, a vampire lord from JoJo’s Bizarre Adventure (one of the player’s favorite anime). The party was trapped on a sinking ship in a mysterious room filled with spider webs, facing down a vampire trying to bring back Dio with a magical amulet. The battle was in the party’s favor, until the vampire’s giant spider phased into the room from another plane of existence. It quickly grabbed its vampire master to phase them both away with the amulet. But before its turn came back around, the players came up with a plan. One of them had a spell that could purify water. Another knew that Holy Water was toxic to vampires. The third had just gained the special ability to shoot water. With the power of teamwork, the party shot a blast of water, purified it in midair, and rolled for maximum damage on the dice. The vampire was never heard from again.

"I have the power of teamwork AND anime on my side!" - Dungeon Master Jaclyn 

Invisibility Goes Wrong For This D&D Boss

This DND boss story does not end well for the boss (as evidenced by its three different condition markers).

Here’s another session story featuring a grand betrayal and a groan-worthy pun.The party had been travelling with Pezzi Zakki, a seemingly-wholesome mushroom creature who had been offering them help in their journey. But secretly he was sabotaging their peace efforts with the plant zombies…and even tried to turn their pet frog into one! When the party realized Pezzi had been the one behind the zombie infection, they cornered it. Its master plan was to cast Invisibility and escape to its lair. But its low initiative roll allowed the party rogue to jump on top of its head, remaining entirely visible and thwarting its plan. By the time the combat was over, the myconid was simultaneously Frightened, Poisoned, and Burned. Don’t mess with the party frog!

“We see mushroom, we kill mushroom, because mushroom not fun guy” - Gandalf, as played by a tween player

Check Out The Story of This D&D BBEG Reveal

The art DM Jesse created for his DND boss reveal. What a throne!

Dungeon Master Jesse has been running his campaigns in the land of XCrawl,  a mashup of livestreaming, extreme sports, and Dungeons & Dragons. In this world, teams of fantasy adventurers compete in reality-show dungeons, streamed live for enraptured audiences. His young adventurers had been fighting their way through a series of giants in a mysterious “Quest Against the Giant King” put together by Dungeon Judge Stonethrower, a giant. When the party finally reached the King, they discovered his true identity: a tiny goblin touting the name King Giant, The Giant King, King of the Giants! Every group that faced him defeated him, but only one delivered the ultimate insult - taking his oversized hammer and using it for the next dungeon. 

“A lot of running Xcrawl is getting in the head of the Dungeon Judges (DJs) that build all these encounters and figuring out what they think is fun. The reveal of a goblin on a throne is what suddenly hit me as the funniest thing that a giant reality TV producer might think of.” - Dungeon Master Jesse

The Most Epic D&D Story Is Taking Down Vecna

DNDs epic stories sometimes come from the strangest of places.
[Image from Vecna: Eve of Ruin]

At the end of Dungeon Master Liv’s campaign, the party had finally reached the end of their quest: entering the lair of legendary D&D baddie Vecna to retrieve stolen sacred scrolls he stole from the pantheon. The final room of the lair was an illusion Vecna built to get the party to turn on the pantheon and work for him. Working for the side of good, the party did not turn. Working for the side of chaos, here’s what they did instead:

  • One character challenged Vecna to a magicless duel, during which Vecna summoned a zombie…which the character promptly ate.

  • One character convinced Vecna to play darts and rolled a natural 20, beating the Lich King at his own party game. 

  • One character took the Hand of Vecna, a legendary item that twists the minds of its users towards evil. But instead of listening to its whispers and doing his bidding, he decided that he’s going to protect the far wall from anything that tries to harm it (...nothing was trying to harm the wall)

  • Another character tried to convince Vecna to watch Sesame Street with the party and their ghost monkey (long story). 

While the King of Liches is trying to figure out what’s going on, the darts player recalled a particular item: a dagger with a 2% chance of an instant kill. He snuck up on Vecna, got a hit, and rolled a 99 on a d100, utterly destroying Vecna’s physical body before the party escaped!

“They in fact, left the scrolls, though. So yeah, we accomplished nothing.” - Game Master Liv

Write Your Own Epic D&D Story

Dungeons & Dragons is filled with epic moments, amazing adventures, and hilarious shenanigans. And we’re pretty lucky – we get to witness moments like this every single week. Our online D&D groups of awesome geek-minded tweens and teens come up with hijinks and boss strategies we could never have anticipated. If you’re looking for a safe, fun place where you can go on D&D adventures with other players your age, why not try our games? You’ve already seen that they’re a ton of fun, but they also meet regularly, are safely monitored by professional Dungeon Masters who work with young people, and feature groups that are put together based on age, play style, and game preferences – which means we set you up for success (even if the dice don’t)!

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A Girls Guide to Dungeons and Dragons