MonkeyDM

How to Make Memorable Fights

Page Chapter
3 Creating Epic Encounters and Monsters
5 Creating A Memorable Boss Fight
8 Creating Great Villains
10 Bonus Chapter: Monsters for Your Games
13 License

Product Identity: The following items are hereby identified as Product Identity, as defined in the Open Game License version 1.0a,
Section 1(e), and are not Open Content: All trademarks, registered trademarks, proper names (characters, deities, etc.), dialogue,
plots, storylines, locations, characters, artwork, and trade dress. (Elements that have previously been designated as Open Game
Content or are in the public domain are not included in this declaration.)

Open Content: Except for material designated as Product Identity (see above), the game mechanics of this MonkeyDM game
product are Open Game Content, as defined in the Open Gaming License version 1.0a Section 1(d). No portion of this work other
than the material designated as Open Game Content may be reproduced in any form without written permission.

How to Make Memorable Fights is published by MonkeyDM under the Open Game License version 1.0a. Copyright 2022
MonkeyDM Publishing. All Rights Reserved
Chapter 1.
How to create Epic Encounters and Monsters
for Your DnD Games
Monsters are one of the cornerstones of DnD, they represent Optional Step:
one of the most powerful tools a GM has at their disposal. Monster Creation / Modification
They can be used to instill fear, excitement, joy, or even pity
in our players' hearts. So how can we make sure that we get So you chose a monster, but you’re not satisfied with the
them right? stats, because it doesn’t fit your game properly. Well time to
alter that stat block or to create one from scratch. Although
Your time is precious, so let’s jump into it: the latter usually takes more time, it’s often more rewarding
to unleash on the players, I’ll let you make the call on this
Here is the 3 and half step process I use in my games after
one.
my many years as a DMing and content creator for the game.

Step 1. Monster Ideation 1. Monster Creation

In the DMG page 283, there are charts to calculate the
This is the 1st step, where we use our knowledge about the Challenge Rating of the monsters you create, but thanks to
party, and where they are in the world to plan the encounter. the advent of technology, no need to complete the tables by
Basically, how challenging do we want things to be, and hand, instead there is this very neat free website created by
what monsters would make sense to use in this particular Reddit user u/itsadndmonsternow, which makes the
scenario. calculations for you.
Once you’ve decided if you want an encounter that is going
to be fairly easy, or something that’s meant to put the fear of
God in them, or anything in between, choose the type of Balance Calculator
monster.

Let’s say the party is trudging through sewers, oozes would Couple of things to note about the calculator:
make a lot of sense there, minotaurs not so much. To be fair,
most monsters can be used in most locations, but it’s nice to First, you need to fill in 3 rounds of damage output, not 3
narrow things down. Alternatively use monsters that are turns, meaning that if your monster has legendary actions
linked to the current villain the party is facing or will face. If they can use during a round, count them in the damage
it’s a lich, use lots of undead, if it’s a dragon, use all kinds of
kobolds and draconic foes, and so on. Second when calculating AoE effects like a dragon's breath
the DMG p. 280's guidelines say to assume that it hits 2
Regarding the difficulty, The DMG has a table for how much targets that fail their save to calculate average damage.
XP an encounter will give for Easy, Medium, Hard, and Unless your effect has a massive range, bigger than that of
Deadly difficulty. The book says to run 6-8 encounters a day, an ancient dragon's breath (90 feet cone), use that to
to spread the player’s resources and offer a legitimate calculate average damage.
challenge. I think that’s BS.
Most games I’ve run, and people I’ve talked to, often only Note: The 2 links above are softwares made for computers, the
have 2-3 encounters max per day (day as in per DnD display may look strange on mobile.
session). So I usually do 1 Medium, 1 Hard, and 1 Deadly
encounter, because I like tough games, but you can go 1 2. Monster Modification
Medium 2 Hard and still offer a fun challenge.
Now if you don’t want to go through the process of altering
If you don’t want to bother with the Tables of the DMG, stat blocks but still want to surprise your veteran players
because they are quite time-consuming, we have a free who know all the monsters in the manual, (or if you suspect
encounter builder on our website that you can use, and there them of looking up stat blocks) a simple thing you can do is
are many others like it that you can find online. this:

- “You are now facing a Death Dog, it’s going to use its web
Encounter Builder attack.
- But Monkey, death dogs don’t have web attacks!
- It’s a special death dog ;)”
Now that you know what sort of DnD monster you want,
now is the time to give it some stats. When creating a How did I do that? Super simple, I used the Death dog’s
monster it’s always easier to start from a template. You can description for my players, but in reality, I used the
use the Monsters provided in the MM or any other book of Ettercap’s stat block. This took me 2 seconds to do. Simply
your choice as your base and alter them for your game. Or look up another monster of the same CR and swap the stat
you can use the next (optional) step blocks, and your players will stay on their toes.
Is it lazy? Kind of. Does it work? Absolutely.
3. Stealing Monsters of the game. (Dark Souls is fun because it’s challenging in a
good way, we want to replicate that sort of engagement). Not
Alternatively, you can also just scour the depths of the every encounter needs to be blood curling, but your players
internet for monster stat blocks custom-made for DnD. On need to know that if they are not careful it will come back to
my website (monkeydm.com) you’ll find plenty of them for bite them in the butt. This way you keep the engagement at
free, and even more fun ones on my Patreon, they are all maximum, nothing to keep someone engaged like fear of
playtested beforehand to make ensure the proper balance. death ;)
It’s rare for players to have seen those, so it gives you a nice
element of surprise. I know because a lot of supporters have Step 3. Executing the plan
told me so.
Now that you’ve prepared your encounter, your strategy, now
Step 2. Strategy Layout is the time where you get your moment and unleash hell on
your players, or at least a fun encounter!
A monster is more than just the stat block it has. It needs to
be considered in the context in which you will use it. Is this
monster supposed to create a full villain arc, like a Dragon Final Note:
or Vampire, or is it going to be used as fodder in battle, or What I recommend doing is having a set of encounters
something in between? planned, around 1-3 of them, depending on how sure you are
of the party going through the route you have intended (cause
Usually, in the stat block and lore, there are indications of players have a knack for derailing stories, don't they ;)) You can
how the monster is used. For example, the good ol’ zombie easily create them, just follow the guide, and whenever the
is made to be fodder, and that's alright. A werewolf on the need for a battle arises, just pull out one of the encounters.
other hand, with proficiency in stealth and immunity to non-
silvered weapons, is made to be an ambusher that will jump
on the unexpecting wizard at the back of the party whilst the There you go, these are my 3 and a half steps to creating
party is traveling through the forest. more fun encounters!

Make sure to implement a proper strategy for your monsters

and to use the environment, it doesn’t take much time to
come up with one, and really adds to the challenge and fun

Art by
Konstantin
Gerasimov
Chapter 2.
Create A Memorable Boss Fight
The big lead-up, the intrigue, the plot, all lead to the lair of What if the boss that you planned on pinning down because
the villain, and now is time for the epic showdown. So let's this has been your main strategy has an ability to teleport
make sure we do it right. away.

Instead of making the mistake that many games make, This is very relevant if it's a smart boss that had time to
where they just make the boss a giant damage sponge, let’s study the party, they would be prepared for the battle to
try giving it more fun abilities. Starting with. come. They pull out a trap card when the party least expects
it, defeating their strategy and forcing them to adapt.
1. The Environment Maybe the rogue has a phobia of water, or can't swim, and
the BBEG pulls a lever, causing the room to become
Let’s look at World of Warcraft, more specifically Sludgefist submerged.
If you ever fought Sludgefist, you know that, like many
warcraft bosses, it has multiple phases, with many varying 3. Time pressure
abilities which force players to play smart to win.
A fun thing to do in your boss fights is to add a time crunch.
For those who never fought him here is a brief breakdown of
its abilities: In the Sludgefist fight the timer is the fact that each time
Sludgefist breaks a pillar, he comes closer to collapsing the
- Chain Link: Links two characters together, if they move too room killing everyone.
far from each other, the chains break and both characters
die Something you can do in a similar vein is to have the party
interrupt some forbidden ritual that will summon Cthulhu
- Hateful Gaze: He charges toward a player, and keeps going from the depths of the Cosmos. They arrive in the middle of
until he hits something, ideally one of the pillars present in the ritual and only have 5 rounds until the ritual is complete
the room. This stuns him and leaves him vulnerable to and the monster summoned.
taking massive damage.
If they fail to interrupt the ritual the monster is unleashed
- Stomp: Yeah that's just a stomp, that one is nothing special 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.
Are you guilty of this crime? The crime: Making boss fights
happen in 2D. I know I was. This is a shame because adding It’s not something that you can do for each boss fight,
a 3D component can create a whole new level of complexity otherwise, it would get repetitive. But it’s a very engaging
and fun to the fight, which isn’t present otherwise feature that you can add each now and then.
But back to our Sludgefist fight, a very cool thing about the
fight are the 4 pillars in the boss room, that hold the ceiling, 4. Phases
and as each pillar falls, the roof of the building starts
crumbling down, falling on the characters. Adding a dynamic I’m sure many of you have already tried your hand at that
environment like that can truly spice up a fight. particular one.

For example, your terrain has flammable material that a As the orc chieftain falls to its knees beaten and bloodied, you
misplaced fireball could set ablaze, changing the terrain. raise your blade, ready to deliver the final blow. As the weapon
Now the crevices on the floor are on fire and the players crashes down towards its neck, an explosion engulfs the
need to be careful not to step on them. battlefield, what’s standing before you is no longer the Orc
chieftain, but a swirling mass of darkness given form, as a
It changes the dynamic of the fight midway through, which is harrowing scream pierces the air, you ready yourselves, this is
great to keep players on their toes. far from over.

Giving a second phase to a boss fight can be a great way to

2. Smart & Dumb Bosses spice things up, it gives new life to your boss, despair to your
players, only good stuff!
As I mentioned earlier, Sludgefist has an ability where he
charges a character until he hits something, be it a player or Wizards of the Coast themselves have introduced Legendary
a pillar, or the walls in which case the room collapses and Monsters with 2nd phases in the form of Mythic Monsters in
everyone dies. the Mythic Odyssey book. Whereupon falling to 0 hit points,
the boss regains a new health bar and unlocks new, deadlier,
I don’t recommend the last ability unless you really really
abilities.
realllly hate your party because rock falls everyone dies is
never fun. But what you can do, is add unique fight elements In one of my Books, “The 4 Dragons of the Apocalypse”
to your boss which forces the party to rethink their strategy. 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:
Art by
Hariina_r
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. If you’re
interested we have awesome Boss Monsters with their full
plan and strategy on Patreon, perfect to amaze your players!

5. Alternative Win Condition

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
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.
Chapter 3.
How to make great Villains
Villains! They often make or break a story. The heroes can Multi-dimensional villains
only be as great as the foe they are facing, and this is
especially true in DnD. The reason why Thanos works great in the MCU, or that
Stradh is one of the most acclaimed DnD villains, is because
So if you want your villain to be closer to Thanos, and
of their depth. They are two very different villains, but both
further away from *check notes* Ronan the Accuser? Who
are also quite similar, here’s how:
the hell is that guy again?

That's right the completely forgettable villain from First, their differences:
Guardians of the Galaxy, the movie is massive, yet no one
remembers the villain. Thanos views himself as a tragic hero, he thinks the world
will face doom if he doesn’t stop it from happening. He says
But this illustrates my point, there are memorable villains it himself, others consider him a madman. But he saw with
and then villains that are passable at best. So let’s make sure his own eyes what happens if overpopulation isn’t stopped,
we make the good kind of bad guys! so he wants to “save” the world, but his means are, well,
questionable at best.
So in DnD, there will be mainly 2 types of villains that you
will encounter, this is a simplification but bear with me. Stradh on the other hand doesn’t view himself as a hero at
all, he knows he is evil, and he knows he’s done despicable
One dimensional villain things. Yet, he has a story that can be relatable to the players.
The reason he is evil is that he was afraid of dying, he felt
The first kind is the Evil Evil Evil villain, they do evil for evil’s himself becoming weak, and to prevent that very real fear
sake, and there is no redemption for them. They want to from coming to fruition, he made a pact. A pact that was
inflict suffering, they want to put people in pain. A monster supposed to give him the love of his life in the process (after
that fits this category in DnD would be a mind flayer. murdering his brother, but you know, details). Instead, he
lost the love of his life, killed his brother nonetheless, ended
As written in the books, mindflayer's thinking is so far up becoming a vampire, and due to all that caught a serious
removed from ours that they cannot be good, they eat brains case of the big sad.
to live, we have a source of brains to offer, henceforth they
need to kill us. So now we know how they differ, but what makes them so
similar?
In addition, their brilliant intellect makes them believe they
are gods compared to us. When you kill an ant you don’t do it Second, their Similarities:
out of malice, you do it because it’s annoying, same thing is
going on here, we are in the way, so they kill us, simple as We relate to them.
that.
We understand where they are coming from, although we
To create these villains, it’s quite easy, think of the word Evil, may wholeheartedly disagree with the way they are doing
and add another adjective, like things, we understand where they come from, we
understand that maybe, just maybe, if we were in their shoes
- handsome,
we would come to the same conclusion.
- charming,
That’s only the first step in crafting a memorable villain.
- manipulative
So now our villain has a clear motivation, but we need that
Starting to sound a lot like my ex... motivation to clash completely with that of the heroes,
otherwise, we end with an anti-hero at best or an ally at
These types of villains can be great in some scenarios, worst.
mostly as a side quest, because of their lack of depth.
Players will feel the urgency to tackle the threat, especially if So let me repeat that: The villain’s motivation needs to
they threaten to attack family members or similar allies. clash completely with that of the heroes. I won’t go into
Stradh’s motivation because of spoiler reasons, so let me
These are the more straightforward villains. When we think explain with Thanos. He plans on killing half the universe to
about the MCU, the first villain that comes to mind is “save” it, which runs quite opposite to the Avengers who are
Thanos, not because of his dashing looks (especially that trying to save everyone. Indeed, if the villain can be rallied to
chin) but because of his drive as a villain. This brings me to the heroes' cause, they’re not a villain. No matter if the villain
my next point: thinks that what they do is good or bad, they cannot falter
from it, or at least not easily, they need to be driven.

Finally, we have a villain that is relatable, whose motivations

are clearly opposed to that of the party, how do we make
sure the party remembers them? By showing the villain's
actions to the party, a lot.
 Art by
It can be done in multiple ways, anything from the villain Warmtail
sending henchmen with their brand on them, to the villain
showing up directly to interfere with the party. And if you
really want to turn up the hate factor, make it very personal.

One good example that comes to mind for this characteristic

was Lorenzo in Campaign 2 of Critical Role. Critical Role
Spoilers Ahead, don't read to italicized portion if you don't
want to be spoiled:

If you're here, then I assume you don’t mind. Lorenzo

appears in person multiple times to annoy the Mighty Nein.
His entrances are grandiose, he literally kidnaps 3 members
of the party. Once attacked, he kills a dear party member,
Mollymauk, and then forces the party to retreat, all while
boasting and bragging. Talk about creating hatred for a
villain.

This is the perfect example of that 3rd pillar, making the

villain known, we know the bad guy, who he is, and what he
does, and we hate him for it. I know you may be tempted to
have a sneaky bad guy that nobody knows about, but don't.
Even if it is only through the action of his servants, the
players need to know about them.

So to recapitulate, make your villain:

Relatable to some extent

Have motivations that cannot align with the party

Be present in the world through their actions

I’ll give you one bonus tip, a little cherry on top, to make your
players really hate the villain.

Make it personal

It’s one thing to know that the dragon is killing people, it’s
another to have to watch your family be slaughtered by their
claws, while you are helplessly restrained by magic. Make
your villains go low, and the players will hate them all the
more.

Anyway, that’s it for me.

If you want to get access to 100+ Monsters that were

carefully made for DnD, join us on Patreon. Thousands of
people support our work there each month, so we’re
probably doing something right.

Take Care!

Evan | MonkeyDM
Art by Kalleeck

Bonus Chapter:
Monsters for Your Game
Here are some monsters that were created for my Patreon.
People seemed to really enjoy them, so I figured that I might
as well share them here with you, enjoy!

Fire Elemental Vanguard

Clad in frozen armor created by their own magic, these fire
elementals have been gifted a higher intellect. This gift
comes at a cost, as they are bound to be the forever servant
of whoever granted this favor, oftentimes this being an
Efreeti Lich. Vanguards shouldn’t exist, made of fire, yet
controlling ice, they are protected by the armor of agathys
spell, and are able to hurl other spells at their foes, casting
webs that they can light on fire with their body, or imbuing
their fists with life draining magic. They pose a formidable
threat to any who oppose them and their master.

The fact that ice magic covers their body of flame creates a
reaction, causing steam to constantly erups from their body,
signaling their arrival in advance to anyone possessing a
keen eye. This armor makes attacking them in close range
an even worse idea than usual, and their new arsenal of
spells also allows them to deal with foes from a distance.
Massacreborn Shade
In stories, shadows are often portrayed as weak, flimsy
entities. This is not the case for Massacreborn Shades.
When enough warriors die in a bloody way, be it war or a
raid, there are times when their shadows all gather, forming
what is known as a Massacreborn Shade. These beings, a
conjuration of remaining emotion and black magic, take
form in the wake of tragedy and only spread more of said
tragedy. They are strong as they are brutal, striking down
entire villages with their chained blades. They are strong
enough to lift an ox and brutal enough to tear it in half,
knowing no mercy and no bounds. They grow ever larger in
the face of death and bloodshed and can hardly be stopped
without members of clergy. If you come upon such a
monstrosity… you better run.

Art by
Warmtail
 Sea Giant
Despite their name, these giants inhabit both sea and
ocean, finding home in secluded underwater caves,
hidden from sight.

They are keepers of sunken knowledge, scouring the

abyssal waters in search of long forgotten lore. Some
shards of History are only known to them, the rest of
the world having long since forgotten. So long as a sea
giants exist the past shall not be forgotten.

In their search they often encounter terrors of the deep.

If they get trapped, one of them will sacrifice
themselves by creating a powerful thunder-wave that
will attract the attention onto them, giving the others an
opportunity to escape, letting the information they
fought so hard to get, live on.

GM Note
Because they’ve fought against the many terrors of
the depths for so long, many sea giants speak Deep
Speech as well as their other languages.

Art by Dean Spencer

Find more on Patreon

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How to Make Memorable Fights Copyright 2022, MonkeyDM Publishing SRL; author Evan Mascaro

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