Most of you reading this may already know about me, Eric, bass player and singer with Gygax, but please allow me to introduce one of my best friends and RPG enthusiast, Henry Glasheen.
Henry is a writer and Dungeon Master based out of Salt Lake City. We both share a love for RPGs and great fantasy literature, and have even collaborated lyrically on the song Demons from Gygax’s first album Critical Hits. I was one of the groomsmen at Henry, and his wife Eleora’s, high-fantasy themed wedding (pictured), and the song Pure Hearts was written as a tribute to their union.
Henry’s campaigns are the stuff of song and legend, and notorious for their clever twists and improvisation. And he’s also one of the greatest people I have ever had the pleasure of knowing.
And so here’s a list we’ve compiled of our TOP TEN D&D “BOSSES” (in no particular ranking order):
Mind Flayer (Illithid)
H: Mind Flayers make excellent boss monsters for mid-level D&D campaigns precisely because they come at you from such an unusual angle. A lot of adventurers are perfectly content to run right up to a hulking brute of a monster and try to cut it to ribbons or blast it apart before they themselves are killed. An adventurer understands that kind of honest fight, but Mind Flayers don’t fight honestly. They send thralls, enslave friends and innocents, and lull adventurers into a false sense of security as their tentacled grip grows ever tighter. These psionic masterminds are perfectly content playing mind games and their long lives give them exceptional patience. The trick is figuring out what they want and how the party stands between them and getting it. Mind Flayer society is loose and mutually suspicious, giving them plenty of reasons for enterprising Illithids to seek out their own power and pursue their own goals, especially if it elevates them in the eyes of their jealous peers.
E: I’ve always enjoyed the aesthetic surrounding these creatures. Especially the fact that they’re so badass that even the dominant races of the Underdark respect them. In an RPG setting, I really enjoy a psionic and psychological battle—it makes the game so much more rich and complex. And, of course, this is what inspired writing The Lascivious Underdark.
Beholder (Eye Tyrant)
H: Nothing quite like a floating ball of ill-tempered arcane artillery to challenge a group of adventurers. Beholders make very interesting bosses primarily due to their twisted psychologies. Their only interest, for the most part, is in their own self-aggrandizement, and they often seek the most cunning and insidious traps to protect them in their secret lairs. This gives any Dungeon Master the opportunity to use their most outlandish and elaborate puzzles in designing any dungeon they might occupy. Once the adventurers have struggled their way through, they should know well the fate that awaits them—fierce, burning eye-rays and a mastermind entirely consumed with godlike arrogance.
E: The Beholder has always been an iconic creature that immediately represents D&D for me. Not sure how it was introduced to me, but it has always been burned in my mind. It requires some intense teamwork in order to overcome such a denizen, as Henry has pointed out. But defeating one is a badge of honor, in my opinion. Sadly, I still have yet to achieve this.
H: When Eric and I were talking about the Displacer Beast, it actually made me think of the excellent first arc of Table Titans, a webcomic about a group of friends who play D&D. I don’t want to spoil anything for those who haven’t gotten a chance to check it out, but needless to say a Displacer Beast can make for an absolutely deadly encounter for any group of low-level adventurers. Pairing their abilities with the sinister schemes of a truly well-realized antagonist can make them a truly memorable foe.
E: The first time I saw, or rather understood, a displacer beast was not from an orthodox RPG, but in the side scrolling D&D licensed games “Tower Of Doom” (or was it “Shadow Over Mystara”…. ?). Anyway, it was so rad seeing the design and then reading up on the creature. There is NOTHING more frustrating in a game than an enemy that constantly evades your attacks. I actually love this monster so much that I got it tattooed on me.
H: Bugbears might seem like a simple, stock enemy by the time a party makes it past 5th level, but when your adventurers are first starting out, these hulking brutes can truly test their mettle. The trick, as always, is to give them a strong motive to oppose the party. It may not be anything as well-worn as World Domination (though sometimes even the humblest of enemies may strive for such things), but Bugbears can seek dominance over lesser creatures in their domain, or to turn the party against their rivals in a long game of inter-gang dungeon politics. I rarely see Bugbears and their ilk utilized to their full potential, but any Dungeon Master worth their salt should see that as an enticing challenge to their story-crafting prowess.
E: Pretty much as Henry stated, they make for great introductory “bosses”. Bugbears are almost a staple for me in an RPG’s first-level adventures. They’re smarter than goblins and kobolds, but not by much. I’m not really sure how much more I can say about them, but when we discussed the idea for a list, the bugbear immediately came to my mind.
H: This one is a personal favorite of mine. Aboleths offer a Dungeon Master the rare and welcome opportunity for true alien horror in a high fantasy setting. Though often neglected and misunderstood, these antediluvian amphibians reek of the same cosmic horror that underpins the works of Lovecraft. At times powerful enough to overtake entire kingdoms of mortals to feed on their intelligence, an Aboleth might serve as the power behind the throne of a foe once thought to be a mere throwaway tyrant. The best way to make an Aboleth truly feel like a boss monster is to play up the tension of an encounter with a truly ancient and dreadful being, and to have the party peel away the layers of misdirection that disguise the being’s dreadful motives. When all is revealed, and the true horror of the Aboleth’s master design unfolds, prepare for a glimpse of true terror.
E: Being less experienced and knowledgeable about these beings than Henry, I still find them incredibly fascinating. There is no higher fear than what you cannot fully fathom. Cosmic horrors have and will always be an interest of mine. And to include one in an RPG story is incredibly exciting, among other emotions. Any storyteller/GM/DM looking for a real challenge to strengthen their talents would do well to run a game with these. Now that I think about it, I wonder if HBO’s first season of True Detective was just about an aboleth after all. Probably.
H: When the party is down on health, all their spells are used up, and the clock is ticking down to the moment when all hope is lost, the Gelatinous Cube arrives with its implacable, mindless imperative—to consume. Though it might not rank high on the list of “most intelligent creatures” (in fact, it would probably try to eat the list), a well-placed Gelatinous Cube can truly feel like a boss when it stands between the party and their desires. It also offers the new Dungeon Master their first opportunity to build dread through providing cleverly hidden environmental details that hint at its presence in the dungeon. Perhaps the winding halls stink of rot and decay, but the floors are mysteriously clean. A blob of cast-off ooze clings mindlessly to a skeleton dressed in the garb of a town guard. The sickening throb of wet, squishing disgust echoes down the corridor, a sound that feels strangely… hungry. The party might remember a showdown with a powerful lich or an evil god-emperor, but a clever DM can turn an encounter with the humble Gelatinous Cube into a story that will be told around the table for years to come.
E: Oh, god. A gelatinous cube. Pretty sure that when we thought about filling this list, this guy came as a joke. But it again, like most of the others, are part of a small core of monsters that increases the appeal and stands as the foundation of D&D. Out of all the devious, terrifying, hulking and complex creatures you can imagine. How often would you imagine something killer Jell-O? Long live imagination, man.
H: Though in today’s world, we might associate vampires with angst-ridden eternal teens and supernatural romance, this creature has all the hallmarks of a truly great villain. I would be remiss if I didn’t mention Strahd von Zarovich, one of the greatest and most well-realized D&D villains of all time. When Tracy and Laura Hickman co-wrote this tragic and yet entirely malevolent creature into being, they came from a time when Vampires were simply one of them many random creatures you might find skulking around a dungeon. However, when they gave one a haunting backstory, a realm of his own, and a whole heaping of haunting atmosphere and dread, Strahd became an antagonist virtually without peer. When you want to give your vampire the kind of presence and sudden terror that leaves a lasting impression, remember that a vampiric villain combines the worst aspects of humanity—greed, pride, and hunger—with an immortal’s patience and planning. Nothing says “evil mastermind” like an undying creature of the night who knows the players’ every move before they make it—after all, they’ve seen it all before.
E: I have to make a departure from D&D here to talk about my first RPG experience… Vampire: The Masquerade. THIS was my FIRST introduction to RPGs. Growing up in a dysfunctional family blanketed in fundamental Christianity, I didn’t get a chance to try RPGs as a kid. My family blamed the devils for his worst work, DUNGEONS & DRAGONS (DUN-DUN-DUUUUUUNNNNNN…… geons!). So, naturally, anything bearing the D&D brand was taboo. Until I came upon a group of friends playing Vampire: The Masquerade. My first character builds were Vampires and, when not misrepresented, are undeniably powerful in a greater sense than most even imagine. When you add in their nuanced understanding of humanity, it makes not only for a hell of a battle, but also a challenge of morals and ethics as well.
H: The Hag is one of the most underutilized boss monsters in a Dungeon Master’s arsenal, a truly potent spellcaster whose larger schemes can shape the ebb and flow of the world. Though we often look at the archetype of the Wicked Witch with an eye of cultural boredom, the Hag has incredible potential as an intelligent and intimidating villain with real power to contend with. The trick with a Hag is to focus on the ways they hide themselves away from the world and disguise their influence. The best Hag villain might only leave small traces of the ways in which they manipulate the events of the world, perhaps only through a chain of extortion and whispered rumors of dark beings hidden in the woods. Their unique aims and propensity for working in covens makes it difficult to estimate the threat they pose, and hapless adventurers may find themselves completely overwhelmed by their incredible magic and cleverly crafted contingency plans.
E: Henry has had much more experience with these than I. The appeal of them in the context that he explains, again, goes back to what I like about the Aboleth. The hidden threats within the threats. I really enjoy a campaign that emphasizes critical thinking and sleuthing in order to gain victory.
H: Games like “The Witcher” have demonstrated the power of any encounter which requires a degree of knowledge and planning to successfully overcome. The Troll is one of the first monsters that a party might encounter where simply stabbing it to death isn’t going to work. Clever adventurers will learn from their first, tense encounter with trollkind that some threats are best fought with dutiful study and the careful application of special items or spells. As a Dungeon Master, one of my favorite things to see at my table is a group of players eagerly preparing for an encounter with a creature with a specific weakness. The more you put threats like the Troll and other finicky creatures in their path, the more like “The Witcher” your campaign will come—with players combining a little lore, a little alchemy, and a little luck to give them the critical edge in a tense fight.
E: This one is great for the fact that lore and studies come into play instead of just outright beating the shit out of something. Learning that Trolls can only be truly destroyed with fire or acid has DEFINITELY come into play when I’ve played other games (such as “The Witcher”). Knowledge is power, and this monster will make you understand how powerful knowledge can actually be.
H: No list of D&D bosses would be complete without the Dragon. To the uninitiated, a Dragon might seem like any other beast—only with wings, armored scales, and a calamitous breath weapon. However, Dragons are virtually unrivaled in their age, intelligence, and experience fighting adventurers. Most of the time, when it comes to fighting one, swords and spells are far less useful than a clever tongue and a quick mind. When it comes to monsters, Dragons sit near the top of the food chain, and they know it. However, their intelligence can be a weakness as well, and their notorious pride can lead them to stay their claws where another being might simply roast a party alive. However, beware of gaining the enmity of a powerful Dragon—no being is more capable of bringing swift, merciless death than these winged kings and queens of the sky.
E: Well, duh. I mean, it’s in the name. Nearly every living human from any culture in any land understands dragons. What makes them way cooler in an RPG is the fact that they possess a higher intelligence than most learned scholars, scribes, sorcerers and such. But outwitting a dragon—THAT’S the height of accomplishment. They have got to be the ultimate bosses in D&D, as well as a lot of other RPGs, for that matter.
Gygax’s sophomore album Second Edition is out now. Get it here