How to Create Memorable Boss Fights in D&D

The big lead-up, the intrigue, the plot, all lead to the lair of the villain, and now is time for the epic showdown. So let's make sure we do it right.

Instead of making the mistake that many games make, where they just make the boss a giant damage sponge, let’s try giving it more fun abilities. Starting with


1. The Environment

Let’s look at World of Warcraft, more specifically Sludgefist

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They don't have a GIF of Sludgefist, so Shrek it is


If you ever fought Sludgefist, you know that, like many warcraft bosses, it has multiple phases, with many varying abilities which force players to play smart to win.

For those who never fought him here is a brief breakdown of its abilities:


- Chain Link: Links two characters together, if they move too far from each other, the chains break and both characters die


- Hateful Gaze: He charges toward a player, and keeps going until he hits something, ideally one of the pillars present in the room. This stuns him and leaves him vulnerable to taking massive damage. This is the ability we will delve into.


- Stomp: Yeah that's just a stomp, that one is nothing special


A very cool thing about the fight are the 4 pillars in the boss room, that hold the ceiling, and as each pillar falls, the roof of the building starts crumbling down, falling on the characters. Adding a dynamic environment like that can truly spice up a fight. I gave examples of such strategies and much more in our most popular free ebook.


Are you guilty of this crime? The crime: Making boss fights happen in flat and non-interactive terrain. I know I was. This is a shame because adding a 3D and/or dynamic component can create a whole new level of complexity and fun to the fight, which isn’t present otherwise


For example, your terrain has flammable material that a misplaced fireball could set ablaze, changing the terrain, now the crevices on the floor are on fire and the players need to be careful not to step on them.It changes the dynamic of the fight midway through, which is great to keep players on their toes. You could even take that to the next level, fill up the room with explosive barrels, now your fire mage will think about twice before casting (or not to be fair).


2. Smart & Dumb Bosses

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As I mentioned earlier, Sludgefist has an ability where he charges a character until he hits something, be it a player or a pillar, or the walls in which case the room collapses and everyone dies.

I don’t recommend the last ability unless you really really realllly hate your party, because rock falls everyone dies is never fun. But what you can do, is add unique fight elements to your boss which forces the party to rethink their strategy.

What if the boss that you planned on pinning down because this has been your main strategy has an ability to teleport away. (We go into more depth about how to create unique monsters and villains, and give you examples in our popular free ebook.)


This is very relevant if it's a smart boss that had time to study the party, they would be prepared for the battle to come. They pull out a trap card when the party least expects it, defeating their strategy and forcing them to adapt. Maybe the rogue has a phobia of water, or can't swim, and the BBEG pulls a lever, causing the room to become submerged.

A good rule of thumb is that the higher the INT score of the villain, the more prepared they are against the party. They will know about their magic items, favorite spells, they can also guess which saving throws they are weak too and so on.


If you’re interested we have more information on how to create epic monsters, as well as some examples in the free book here.


3. Time pressure

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A fun thing to do in your boss fights is to add a time crunch.


In the Sludgefist fight the timer is the fact that each time Sludgefist breaks a pillar, he comes closer to collapsing the room, killing everyone.

Something you can do in a similar vein is to have the party interrupt some forbidden ritual that will summon Cthulhu from the depths of the Cosmos. They arrive in the middle of the ritual and only have 5 rounds until the ritual is complete and the monster summoned.

If they succeed in interrupting the ritual, kudos to them, give them some sweet loot. If they fail, the monster is unleashed and from there the players have to chase it and/or run away, prompting another potential story arc, or the fight gets tougher, or everyone gets knocked unconscious and wakes up amidst a strange new dimension. The choice is yours really.


It’s not something that you can do for each boss fight, otherwise, it would get repetitive. But it’s a very engaging feature that you can add each now and then.


4. Phases

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I’m sure many of you have already tried your hand at that particular one.


As the orc chieftain falls to its knees beaten and bloodied, you raise your blade, ready to deliver the final blow. As the weapon crashes down towards its neck, an explosion engulfs the battlefield, what’s standing before you is no longer the Orc chieftain, but a swirling mass of darkness given form, as a harrowing scream pierces the air, you ready yourselves, this is far from over.

Giving a second phase to a boss fight can be a great way to spice things up, it gives new life to your boss and despair to your players, only good stuff!

Wizards of the Coast themselves have introduced Legendary Monsters with 2nd phases in the form of Mythic Monsters in the Mythic Odyssey book. Whereupon falling to 0 hit points, the boss regains a new health bar and unlocks new, deadlier, abilities.


In one of my Books, “The 4 Dragons of the Apocalypse” I’ve created the 4 horsemen of the apocalypse as dragons, and the last horseman is “Death”. I made her a mythic monster. Let me show you:


Pretty cool art right, it was made by @hariina_r on Instagram

I won't delve into her fighting strategy here, but as you can see when she reaches 0 hit points, thanks to her Embodiment of Death trait she regains all her HP and has the spell armor of agathys automatically cast on her at 9th level (as you can see described in the Mythic Actions). In addition, while the temporary hit points are there, she gets access to fun new abilities, teleportation, damage, and so on.

It adds a very dynamic element to the boss fight, as players don’t know what to expect from the new phase. I gave many more exemple of memorable traits to give to your villains in our free ebook, some of which are quite deadly, or so I've been told ;)


5. Alternative Win Condition

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In the Campaign of Critical Role, the last boss Vox Machina had to fight was Vecna, an all-powerful lich with eyes set on godhood. One of the unique and fun things about Vecna was that to win they couldn’t just reduce him to 0 hit points, as is the case with other monsters. Instead, they had to plant trammels in the body of the lich, and finally incant a ritual from a celestial book.


The fact that the Boss fight required not to bring Vecna to 0 hit points, lead to a very unique encounter, where in the last rounds of the battle, the party had to hold back their blows in order not to kill the Lich. Doing so would have allowed it to escape and to come back stronger.


Giving players another way to win changes the whole dynamic of a fight, and keeps things fresh. All of a sudden, it's not bonk the big thing till it don't move, instead it's keep the devil busy until the celestial armies arrive, or cause the giant to fall and collapse the floor with him, trapping him below. These are the sort of boss fights that players will remember for a long time, because of how unique and epic they are, so if you take away anything from this article, let it be this.


If you're interested, we made a free ebook that goes tackles all aspects of monster and villain creation, to help you create something truly memorable at your table. Until next time, take care! Evan | MonkeyDM

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