D&D 5E What makes boss fights memorable?


Moderator Emeritus
Here is a set -up for a final boss battle I did back in the fall.

1. Flooded chamber.
2. Minions (trog scouts with bows) and a lieutenant spellcaster (who despite this set-up video were using their camouflage powers to be hidden until the party approached or passed).
3. The boss (a custom spirit naga) and her dominated child human shield.
4. A strange purple orb on a stone base and a big ole treasure chest that might have useful things in it.
5. Crocodiles lurking in various places in the water
6. A fallen stalactite (that is actually a huge injured piercer)

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4.) Violence is not always the answer: Make sure there are elements that can be resolved without a fireball or sword. They don't need to be mandatory, but having the option of doing something other than casting a spell or rolling an attack roll makes things interesting.

I had set up a boss fight and one player bartered a fae favor to the BBEG in return for "going far away". The encounter was over in five minutes, but that one PC made a significant sacrifice and neutralized a significant threat made a big impression on the party and made it quite memorable.


Mind Mage
We play theater of the mind. But sometimes the boss fight is extra complex tactically, and we pull out the grid and minis to keep track of everything, and that in itself is memorable.

Storywise, the boss fight is the climax/confrontation at the end of the story. What makes the confrontation satisfying, is that the heroes actually die in some sense, and the source of all of the conflict - and the cause of the adventure in the first place - actually defeats the heroes.

The heroes dont win by their own power.

What saves the heroes is actually some poetic justice, where the moral of the story comes into play and resurrects the heroes (literally or figuratively) and empowers the heroes to overcome the source of the conflict.

In order for the boss fight to feel satisfying, the DM needs to foreshadow the moral of the story long before the final confrontation. Maybe the moral is to be kind to the poor, and doing so happens to motivate a poor person who is key to overcoming the boss. Or whatever philosophical point is that the DM thinks the players will find interesting.

It is the ethical message of the story that defeats the boss.


He / Him
I just want to give a big appreciation to this thread. Next month we are wrapping up a campaign that's gone on since the first November of the pandemic, and this thread has helped me come up with a very engaging end fight with multiple goals and outcomes!


In 5e times, we have played 6-7 campaigns and the 2 I remember mostly is the first one with my son who rolled crit, crit,crit over the three rounds and defeated the boss by himself leaving the henchman still fighting giant rats. Not at tough as a fight as I thought.

Last campaign ended a few weeks ago when the fighter charged out to fight the dragon Cryovain himself and was doing ok. When one of the NPCs came out to help, the fighter went hit, crit, action surge, crit, hit. 113 points of damage in one round with the dragon slaying sword later the fight was over.

We played the Apocalypse campaign and The boss fight was ok, but not as memorable as these others. Maybe it is the crits, but maybe the luck of the situation.

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