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D&D: Looking For A Boss Fight? Here Are Five Low-Level Boss Encounters

4 Minute Read
Jun 3 2020

Tired of fighting the same old bugbear/ogre/The Spider? Try one of these great low-level boss monsters, the perfect match for any starting questers.

Boss fights are a part of our collective unconsciousness. Like some nameless, archetypal beast that’s expressed itself in primal fears or, in this case, video games and regular narratives, we all sort of have an innate understanding for what a boss fight is, even if we don’t quite understand how to properly construct it. By and large it’s: the toughest fight is saved for the end, the idea being that characters will have already expended several of their resources and have to scrape by a victory through the skin of their teeth.

But in a D&D game, it’s a little more challenging to bring that to bear because it’s an expectation that’s so familiar and that makes so much narrative sense that players will see it coming, and the very idea of a boss fight is something they plan for. Often times this means holding back on their biggest and best spells or strongest attacks so they can be fully topped off when it comes to taking down the boss and utterly pasting them in a round. This is a challenge that probably deserves its own article.

For now, these are five great boss monsters that you can drop on a low-level party and they’ll be a blast to fight, even if your party is amped up and full of potions that they were supposed to use a few levels ago.

Barbed Devil

Let’s start strong. A Barbed Devil is a dire threat to a low-level party. With over a hundred hit points, they’re a challenge to take down even for a party at their CR5. But throw them at a party of 3rd or 4th level adventurers, and they’re in for a rough time. Why would you do that? A barbed devil has a lot of resistances that help them stay alive, but that also teach new players some of the concepts in the game: you can get around resistances by prepping the right kinds of weapons. Characters attacking with silver sword or certain magic spells have no trouble getting through the creature’s DR. But even then, with magic resistance and powerful attacks it’s still a threat up close or at range. This one monster works as a great “summoned creature.” I love using them as a creature that a bunch of low-level cultists are trying to summon or control or whatever, and the players might be able to stop the ritual–but if not, watch out, it’s time for a tough fight.

Blue Dragon Wyrmling

White Dragon Wyrmlings get all the love in this game for some reason. They’re the lowest CR dragon that you can throw at a party, sure, but why fall back on the weakest when you could show off the majesty of a Blue Dragon instead. Blast them with lightning, fly out of range until your breath recharges. With the ability to fly and burrow, a Blue Dragon wyrmling makes for an excellent foe to drive off. There’s no shortage of ways it can escape as long as it flees in time.

Of course, it can return later (or perhaps return with a parent, depending on what sort of time shenanigans you are and aren’t willing to pull in your campaign), bigger, badder, and out for revenge.



I love Flameskulls. These are the skulls of mages who have been slain and bound to serve as guardians. Obviously we’re going to subvert that for our low-level adventure. Why not have it be the spirit of an ancient mage whose will was strong enough that it broke free of its servitude, and now, mad with megalomaniacal power, it’s going through rallying what forces it can to remake the world in its image.

But it’s also just a floating, on-fire skull that keeps coming back unless you specifically bury it in a grave with holy water or dispel magic/remove curse it. So for a low-level party that doesn’t know this, this is the gift that keeps on giving. Like a bad penny, it will always turn up.


There wolf. There castle. There a challenging humanoid enemy that’s a brute to fight and works rather well as a villain because you can have anyone be a werewolf, and then change mid-fight to show that the fight is getting REALLY intense now.

Kraken Priest

Finally, what would a batch of low-level villains be without a charismatic cult-leader who calls upon eldritch power from abominations deep within the sea. A Kraken Priest is a great villain that can support a bunch of minions. Between their powerful spells and abilities that make fights with them not just dramatic, but downright theatrical, these are the posturing spellcasters and scenery-chewing monologuers that you’ve been dreaming of since the party was level 1. But wait until they’re like level4 to hit them with this priest and some minions.


So the next time you’re looking for a boss monster, try one of these!

Happy Adventuring!

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