Your most memorable/challenging battle.

[Spo]

This thread was inspired by the discussion in the meanie Dm/ realism thread. Someone mentioned there that their most challenging fight was one they talk about years later.

Here’s mine. Our party of 6 at lvl 15 (I think) going through Mad Mage then in our infinite wisdom decided to take a short rest in the gythyangki (sp?) base. I remember our Dm asking us several times if this was something we really wanted to do and we kinda figured we would take that risk. Upon exiting our resting place we were greeted by about 30 plus solders backed up with a couple of dragon riders.

It was chaos fighting our way out of the situation. Since our table is not much for meta talking during fights, we had players doing crazy stuff without coordination with others. Our barbarian just ran into the largest group right before our wizard was going to throw up a stone wall to cut them off. My monk ended up dancing with a dragon rider and his mount for most of the battle at the exit while the cleric was working hard to keep the bard alive as he was cut off from our main party.

Although we didn’t defeat them all, just escaping that situation was one of the best encounters we had during our 2 year campaign.

[DarknessEternal]

My greatest ever D&D fight was against a Beholder.

It was in a specially designed room to give it every advantage: high ceiling, spike pits, magical darkness. We almost immediately started losing, and quite badly, as the party is basically all melee combatants. One of our guys took the petrification ray and failed his save. I dashed up and threw a Polymorph at the Beholder. I assumed it would easily pass the save, but my whole goal was to get a Silvery Barbs off to give my friend advantage on his next petrification roll.

But one failed save later, we now had a Beholder temporarily turned into a fish. Why a fish? I needed it to have 0 speed so it couldn't just walk into one of the spike pits and become a Beholder again. We had no chance of beating it in it's lair. But now we were still on the clock, fish can't breathe air, so we assumed something as smart as a Beholder would intentionally not hold its breath, and drown itself to revert back to Beholdering. Through a combination of Misty Stepping and dashing, I scooped up Mr. Fishy and ran him as far away as I could get from the death star room to a tiny room that was earlier in its lair.

And there, we made our stand, surrounding it so it couldn't put everyone in the main eye. It wasn't pretty, Beholders are strong, half the party was unconscious when it finally died. There's no way we could have fought it inside it's doom room.

[Eldariel]

Well, I'm mostly a DM so my most memorable battles typically come from the other side of the screen too. I would have to say the one that stood out the most to me (or at least occurs to me now thta I reminisce) among all the epic fights, was the epic fight between my level 4 LMoP/DoIP/ToD/SKT party (Vuman S&B Battlemaster 4/War Cleric 1 with Shield Master, +4 Wis Res: Wis, MDwarf Abjurer 5 with Res: Con and +2 Int, Vuman Lore Bard 5 with +2 Cha, Inspiring Leader and Res: Con Strongheart Archer Gloomstalker 5 with Sharpshooter and all with bonus feat on level 1) and Venomfang. I gave Venomfang lair actions of an Adult Green and spellcasting (Fog Cloud and Misty Step), otherwise it was largely by the book. Party also had Protection from Poison on the two missing characters from Reidoth who had hired them to rid the town of Venomfang, opting to avoid risking the confrontation.

The party aside from the GS (hiding outside) got kinda suckered by Venomfang sowing discord against Reidoth and asking for help against Hill Giants that "stole its eggs" and...long story, but they got surprised by a venom blast to the face. I let Shield Master apply to all breaths be they Con or Dex but the surprise condition prevented its use. The party took significant damage in spite of the resistance. The fight ensued with Fog Cloud dropping to Concentration from Magic Missile, while the Battlemaster was Fly + Enhance Abilityed to shove the Dragon down (forced some Misty Stepping on its part) and the GS kept shooting. The GS got downed due to vine grapple followed by advantageous attacks, the Bard got dropped and picked up to. Ultimately Venomfang got knocked down to 2 but able to keep a Fog Cloud up, the Bard made the fateful decision to try Vicious Mockery instead of Cloud of Daggers, the Battlemaster blocked the escape route but got one-rounded to 0 by Venomfang in the Fog Cloud, and it managed to escape with the Gloomstalker missing his last shot.

It was an epic battle from the setup to the finish to which I can't do justice here since it's been so long, it ended in a pyrrhic victory for the party (managing to drive it out of the tower allowing for "delairification") but the dragon lived, allied with the Cult of Dragon, who in turn formed a loose partnership with the Cragmaw to take down the PCs specifically (after their repeated goblinicide and attacks on Cult operations). It had the PCs seeking out and eventually finding the Dragonslayer Sword which ultimately turned out to be Venomfang's downfall in a latter fight with a brutal turn from the BM involving two hits and one crit for a ridiculous number of dice. Also had them form a close alliance with the Emerald Enclave and Reidoth in particular becoming a pivotal NPC. It would not be an exaggeration to say that the way the battle turned out shaped the whole campaign. Honestly, the reason I find it so memorable is probably that the dice and player/NPC decisions conspired to make the whole arc work out so incredibly well, but the initial fight was epic in spite of no PC fatalities (in fact, no fatalities on either side).

[Danielqueue1]

We were at epic levels. We had beaten the DM's mega-beasts and armies with ease. We were a coordinated and tactical party that knew how to divide and conquer or pull a fighting retreat. We were overconfident. A city in the outer planes besieged by the undead? an NPC letting us know about a secret entrance? Bah! What are we peasants!?! We go through the front door! We crushed the undead army and politely knocked on the front gates to be let in. But that isn't this story. We were high on the power of high level crushing everything in our way. With two casters with simulacrum, (one had to use wish to get it) 2 summoned celestials, and an optimized healer (pre-errata healing spirit being a big part of it) we set out to kill the self proclaimed Lich God of the Abyss in his floating upside-down pyramid fortess above the river styx.

The dungeon was BONKERS one teleportation trap lead over a pit that dropped straight down 1000 feet into the river styx, another lead into a room with a shadow dragon AND a dracolich (our Kensei monk had to survive on his own long enough for us to catch up. Each room could have been the final boss of a lower level campaign! But we were at epic levels.

When we get to the top of the pyramid (the largest floor because it was inverted) we had used some resources but we were still excited.
The boss fight spanned the whole floor, the teleportation traps from earlier were the only way between rooms so we wouldn't know what was there until we got there. The boss knew the layout, we did not. Before we even get to the boss, there were swarms of lesser undead, two death tyrants, tag-team liches, death knights, a real highlight reel of undead baddies.
The Boss popped in and out harrassing us as we were slown down by his minions, but would often be waylayed by our martial with the Sentinel feat for a few rounds at a time. The most terrifying thing about this boss? He knew and had prepared EVERY SPELL IN THE GAME (except healing and holy because undead) and had UNLIMITED spell slots of level 8 and lower. With one 9th level spell slot for EACH 9th level spell it knew. (Which was all of them) and he used them liberally.

Our saving grace was a 9th level globe of invulnerability that it became priority 1 to protect the caster that had concentration on the (relatively) safe-bubble. We chewed through that fight and every room was a tactical chess game. Readied actions to move instead of dealing damage because getting left behind from the bubble when the boss popped back in was terrifying.

Once we got the boss trapped in a narrow hallway (the rooms were barred against teleportation through the walls other than the runes ) and we were doing absurd damage to it, but it was also able to reach through our bubble. The bubble popped, the Lich-God laughed until the simulacrum re-cast it.

The boss broke through into the next room and we followed. Then he made a desperate gambit. He ripped off the roof of his own fortress and cast meteor swarm centered on himself.

Counterspell didn't roll high enough.

Globe of invulnerability doesn't touch 9th level spells. Concentration was broken. Our Simulacrums, vaporized. All of our summons, gone back to their home plane. One PC unconscious. Everone except the monk not far behind. It was do or die. One character bit the dust. And we were wondering who was next when the boss got his legendary action after the current character's attack. But then the DM asked. "How do you want to do this?"

We spent well over a month of real world time in that dungeon that took our characters less than a day. And we still talk about it years later.
Seeing as the war between this guy and another deity was supposed to be a backdrop for our quest and instead we took it up as a sidequest the DM gave us plenty of warning that it was not balanced in the slightest. The DM admitted that we had been crushing every "balanced" encounter he sent our way so he didn't even try to balance this one. And it was Glorious!

[thorr-kan]

I'll limit this to 5E, since that's where we are.

This was last winter, over a Discord server. Four 3rd-level characters: a rogue, a ranger, a paladin, and my warlock 2/sorcerer 1. We were dungeon-crawling a temple complex when we became aware that yuan-ti were stalking us. We got herded into a room by a mass of snakes with at least 3 yuan-ti half-bloods.

We setup a choke point at the door, and I put a fog cloud into the hallway so they couldn't see what was happening. The mass of snakes came first, and we murder-lized them. Then we heard some chanting, and my fog cloud got dispelled. Into the room spilled a two-weapon fighter, an archery ranger, and a cleric, who's capable of casting 3rd level spells, while I don't have a slot over first.

Crap. <Caster fight! caster fight...>

We get initiative, and combat ensues. I'm hollering for our team to engage their fighters while I deal with the priest. Our rogue and ranger start an archery duel with their ranger, our paladin engages their two-weapon fighter, and I drop a high-damage guiding bolt on the cleric. We roll well, they don't.

At this point we pause for the night. The DM mentions we'd gained enough XP for 4th-level. We can level up mid-battle and continue next week. I choose another level of sorcerer for the spell slot and the spell points for another spell slot.

As we restart, my guiding bolt had ruined her concentration and her buffs. Combat ensued with our side getting in good hits but getting poisoned. I burn through all my slots dropping guiding bolts while dodging melee attacks and resisting incoming spell effects.

In the end, I dropped the cleric, then helped clean up the melee combatants with a vicious mockery to put down the fighter. Combat ends with everybody poisoned and hurting but me! The paladin and I then get everybody as good as we can and we find a place to fort up for the night.

Our combined 12, then 16 levels manager to put paid to at least 18 combined levels of bad guys. We might have pulled it off if the DM hadn't let us level-up mid-fight, but I won't lie: it was looking pretty grim.