D&D 5E (2014) Share your Dnd "Moments that Matter"

First one I thought of was back in 2e days with a travelling merchant that was accepted into the PCs camp for the night. He was a bit cagey with the PCs, so they decided to see what he had in the back of his wagon. Turns out he was a chef that just published his first book about mushrooms and was selling it up and down the coast. One of the PCs threw his book at him saying, "Who reads this sh..."
 

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As with many im sure, who have ran Sunless Citadel, have fond memories of Meepoo. My group loved Meepoo. They took him in after befriending him in the citadel. I didn't think they would care that much for him, figured he was going to be just an NPC. He lived with the party for a while in Phandelin. One day the party discovered Belak didn't truly die and came back as a lichen lich. Meepoo had been keeping tabs on the party for Belak while he regained power. Some players hated Meepoo for the betrayal, some pleaded with him to come back haha. It was a fun battle.
 

In the days of AD&D my DM dared a character to have sex with a sheep. The player balked. The DM offered a free level. The player... deliberated, then accepted. The player then described the act of sheep sex with their dwarf.

It was like a strange game of chicken, neither one backing down. We were all the losers that day.

The dwarf got his level! But died to a frying pan knocking him out a 2nd story window about a month later.
 

1st Edition days. Party is in a dungeon crawl. Battle erupts in a 30 x 30 foot room. Mage decides to cast Fireball.
Players all shout "No!" I confirm with the mage's player that that is what they want to do. Their response? "Sure I do! We're all high enough level to survive!"
Except the mage. Who failed his own save. And was wearing a nearly full Helm of Brilliance. Which also failed its save.
The resultant chain reaction explosion (which, of course, set off pretty much all the rest of the party's other magic items) left no identifiable remains of the party, and a large, smoking crater where the dungeon had once been.
That was probably 30 years ago. A Helm of Brilliance has never appeared at our table again.
 

1st Edition days. Party is in a dungeon crawl. Battle erupts in a 30 x 30 foot room. Mage decides to cast Fireball.
Players all shout "No!" I confirm with the mage's player that that is what they want to do. Their response? "Sure I do! We're all high enough level to survive!"
Except the mage. Who failed his own save. And was wearing a nearly full Helm of Brilliance. Which also failed its save.
The resultant chain reaction explosion (which, of course, set off pretty much all the rest of the party's other magic items) left no identifiable remains of the party, and a large, smoking crater where the dungeon had once been.
That was probably 30 years ago. A Helm of Brilliance has never appeared at our table again.
so basically
 

After years of playing and DMing dnd, I have found that plots fade, campaigns become fuzzy, but there are certain moments in the game that become immortal. Those moments of incredible luck, or brillance, or just plain hilarity that stick with players for years. Its the moments that turn into the campfire stories your players still tell all those years later.

A few moments:

1. Playing a 13th level Goblin Enchantment Wizard, we are getting our but kicked in the campaign final battle. I misty stepped right up next to the BBEG and broke my Staff of Power. I killed myself, didn't kill the BBEG, but severely weakened him to where the rest of the party was able to knock him out. Only time in over 40 years of D&D I've seen that done.

Icing on the cake: The campaign had an element where there was a set of crown jewels that multiple factions were trying to get to establish their leader as the rightful King/Queen. We found them earlier and I put them in a Lemunds Chest for safe keeping. There was a minor conflict in the party where 4 of the party members supported one faction and their woman leader for Queen. Myself and one other PC really did not like her as the queen. We begrudgingly agreed go along to get a long, but when I died the Chest was lost with me, so she did not get to crown herself.

It was a great way to end a campaign.

2. Playing a 19th level Eladarin Glamour Bard/Order Cleric and we were facing a probable TPK. I (player) was hammered, it was the end of the night and I had had about 12 beers. We were fighting a 2 BBEGs on a boat, one was low on hit points but kicking our butt, the other BBEG was near full hp but had flown off due to the fear spell, he was no longer frightened, but was still 2 rounds from getting back into the fight. I was on the ground prone at like 25hps, the Rogue was downed right next to me, the other 2 PCs were about 50 feet away on the other end of the boat, one was held and downed the other was held and at low hp.

It was the BBEG turn and I had a plan, but I needed the BBEG to stay next to me. The BBEG didn't think I was much of a threat because I was prone and had been held for a turn or two, so he went to leave. "I said NO, I make an AOO" ... My PC had a 9 strength and was not holding a weapon ... The DM said "what" thinking I was just drunk. I reiterated if he is leaving I am kicking at him as he tries to leave. Still thinking I was drunk - "Ok you are prone make an attack roll with disadvantage" I hit and after a debate about whether I did 1 damage or no damage - the DM said ok he attacks you with advantage instead. I got hit but survived. So then on my turn I stood up, grappled the unconscious Rogue, held him up so he wasn't prone and then cast Healing Word on him, as his eyes opened I said "I affected him with a spell so with Voice of Authority he can make an attack" 19th level reaction sneak attack wiped out the BBEG. The DM said it was the most brilliant thing he had seen a player do in combat.

By the time the other BBEG got back to the boat we had managed to heal up quite a bit and he was not much of a problem.

3. First edition Curse of Strahd, I was DM about 1985. Party was getting killed, three PCs fled from some Vampires (or Vampire Spawn?) up stairs of a tower, while the Paladin does the 1980s Paladin thing and blocks the stairs sacrificing himself so the rest can get away. They get to the top of the tower and it is a room and a dead end. One PC spikes the door (something you could do in 1E). The others start chopping a hole in the wooden ceiling. The Vampires have killed Paladin and are a round or two behind them and they are on the other side of the door breaking through. The party gets the hole in the roof and also realizes there is a bunch of oil barrels in the room. They break the barrels of oil in the room and then jump to another tower about 100 feet below. 2 of the PCs die from the fall, 2 survive one had a Ring of Feather Falling I think and the other one barely survived after taking the damage. Once they get on the tower below they shoot a flaming arrow up into the tower they jumped out of, blowing it and the Vampires up. This ended our first Strahd campaign as the remaining 2 PCs fled the campaign. I don't remember how they got back to the real world.

4. Put a dead Halfling PC body into a Handy Haversack so we could bring him to town and ressurect him. Forgot the PC had a bag of holding ..... oops!
 
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