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 Remember that wicked obsidian dragon that trapped us all in a portable hole and then froze us at the bottom of the river? What was up with that? Even when the players who weren't there that session brought their guys in to the rescue, they got popped. We had to go to the equivalent of Gamma Flight to finally beat that thing. That went from a throwaway adventure to one of the most memorable encounters in no time flat.
Do your players engage in this sort of conversation from time to time? If not, you might be selling your villains short. Let's see what our gaming brothers have to say about memorable villainy.
Andy: By the time I was in high school I'd run many campaigns, both short and long, and hundreds upon hundreds of encounters.
But ask any of my veteran players which encounter from the old days they remember most and they're likely to describe a particularly nasty encounter with an obsidian dragon named Nightfall. What started out as a simple dragon hunt took a decidedly unorthodox turn when the characters' prey turned out to be a lot cannier than they expected.
The adventure, inspired in part by the instant classic "Into the Flames" from issue #1 of Dungeon Adventures magazine, featured a very powerful, very intelligent dragon in a lair built to maximize his abilities. Traps, scrying sensors, peepholes, secret passages -- this dragon was good and ready for a pack of pesky PCs to poke around.
Greg: Our party was pretty high level by then . . . my guess would be at least 12th, but the exact details are a little fuzzy. We'd taken down slavers and giant kings and forces of elemental evil . . . even though we knew a dragon was in that cave somewhere, we weren't worried.
I do recall using one of our tried-and-true methods of entry: stone shape a narrow entry point, everybody piles into the portable hole, a wild-shaped druid carries it through the hole, and then we find a safe place to unload before laying the down the hurt. (Stone shape also was great guns during D3: Vault of the Drow -- we'd go to the roof of a clan house, stone shape a peephole, look in to see if it opened into the main chamber, and then start pumping charges from our wand of steam and vapor in there. Mmmm, who wants steamed elf?)
But this time, we weren't so lucky.
Andy: Somewhere along the line I read advice on how to play a villain smarter than me, which basically said, "Pretend that he can guess what the PCs are going to do next." In this case, that meant that he was waiting at the other side of the tiny stone-shaped tunnel with a powerful enchantment spell. I took Scott (the player of the druid) aside and watched as he failed his saving throw against spells. Calmly, the dragon took the portable hole from the ensorcelled druid and carried it to the bottom of the icy river running through his cave. (I don't remember exactly what happened to the druid. Maybe Nightfall ate him first.)
Then I went back to the rest of the players and described how, after a longer than expected wait, the portable hole opened up . . . and a frigid waterfall fell on their heads. Before they could react, the dragon's icy breath had frozen the entire contents of the portable hole into a single cylindrical block of ice (this tale was mentioned in the Episode 10 podcast.
Greg: Like I said, we had faced many daunting foes before. But this was the first taste of total annihilation . . . it didn't sit well. This was 2nd Edition, and I still felt very attached to my lovingly crafted halfling druid/thief-acrobat. What in the world were we supposed to do?
Luckily, a couple of our players weren't there that session, so we scrambled next session to put together a back-up group of leftover PCs and prominent NPC cohorts and allies. When that attack failed, we were down to the bottom of the barrel, but we finally overwhelmed Nightfall with sheer numbers. The dragon certainly wasn't your typical recurring villain, but it left a powerful mark.
Andy: Nightfall wasn't designed as a long-term or even necessarily memorable villain, but circumstances conspired to fix him in the memories of the players for the last two decades.
One of the earliest NPCs to become a recurring thorn in the side of the characters appeared in my Planescape campaign some years later. Most of the characters were either new to Sigil or simple outcasts. Perhaps unsurprisingly, they quickly fell in with an unsavory element: the seedy underbelly of planar society.
Specifically, they stumbled upon that staple of late-night martial arts movies: a bloodsport arena.
 Greg: If you're a regular reader of this series , you already know about Suleidan Kithkani . He owned Dawthdun the minotaur gladiator (played by our friend Kevin), and he was pretty fair with a cutlass as well. When in doubt, the party liked to mix it up in the ring.
After several successful fights, Suleidan developed a rivalry with a wealthy rug merchant (whose name, sadly, has been lost in the sands of time). Some petty insults, a bit of gladiator thievery, and other hijinks went on over the course of several sessions.
Finally (and foolishly), Suleidan would have no more and challenged the merchant to set up a fight -- any fight -- against the PCs. We were 5th level, and what he threw at us would probably be an EL 10 encounter had this been 3rd Edition. The upside? I got us 10:1 odds and put 5,000 gp on the good guys. And you know what? We won.
And then skipped town.
Andy: This was one of those times we DMs love: when a variety of unconnected events come together to inspire a memorable storyline. I'd actually written up the bloodsport arena (and most of its gladiators) for aDark Sun game I'd run a few years earlier in college. When the characters were looking for some trouble to get into, I pulled out my notes and let them get a little bloody and win some gold. The activity proved so popular with the players that the arena became a recurring site . . . and the NPCs affiliated with it, including this merchant/gladiator owner, became recurring characters.
The rivalry didn't take much work to establish -- just show a little disrespect to my players' characters and the rest virtually writes itself. And when he suddenly owed the PCs a cool 50 grand that he couldn't fork over, escape from the city was the obvious trick that'd really peeve them.
Greg: Since we were in Sigil, "escape from the city" meant he could have gone anywhere. We knew we weren't going to find him right away, so we put it on the backburner while earnestly vowing to track him to the ends of the multiverse.
Andy: The PCs didn't get entirely shafted. They took over their rival's storefront, which gave them a steady (if paltry) income. What's more, it gave them a reason to stick around and set down roots. Next thing you know, they're living in a manor and running a thriving mercenary business.
That's a long way from battling sweaty barbarians on a blood-slicked floor while a crowd of lowlifes and the occasional demon or devil are screaming for your head on a pike. ("So, Jimmy, do you like gladiator movies?")
Of course, the PCs eventually caught up with the welcher. Months later, they tracked him down on a distant world and collected on their bet by putting him to work for them.
That brings up a really important point for DMs: A sense of closure is extremely important for players. There's little that's more frustrating than knowing that the bad guys got away from you, and almost nothing better than making them pay for their evil deeds (including the gall of escaping you in the first place). Almost every unsatisfactory gaming experience I can remember (both as a player and DM) was at least in part due to the knowledge that the villains had thwarted the PCs and that the players couldn't see how they'd get even.
 Greg: Speaking of getting even . . . having been on the receiving end of twenty years of Andy's villains, I welcomed the chance to make my own. When I started planning my Island campaign, I wanted to have a key villain. I'd already decided there would be a strong "false identity" theme, so I made a list of all the monsters with the shapeshifter type. (Ironically, I threw out hengeyokai even though it was an Asian-themed world.) It turned out to be a different Eastern mythology that provided my villain: the rakshasa. But not your run-of-the-mill backward-hands tiger man . . . I went with the ak'chazar version from Monster Manual III. Since this was a city-based campaign, I clearly needed a crime lord, and a necromantic shapeshifter mastermind fit the bill.
Knowing that Ishinomori would be my ultimate figure of evil, I then set out to craft a world where it wasn't obvious he was the only bad guy. Long before the PCs even knew of a dark figure named Ishinomori, they encountered the Almighty Ayabito, another crime boss. He had the PCs run a few missions (of questionable ethics) for him, but never made them perform outright evil acts (he didn't want to lose them as powerful agents). But because the PCs were introduced to him as a figure from organized crime, they never quite knew if he was just bad, or truly evil.
Andy: And some of us didn't really care. We just wanted the gold.
Greg: Ishinomori even used this knowledge to his advantage, setting up a meeting with the PCs at the Almighty Ayabito's regular restaurant, disguised as the Ayabito himself. When Lotus Blossom started asking questions the rakshasa didn't know the answer to -- and Nat Mason subsequently flipped a table trying to start a fight -- Ishinomori knew it was time to reveal at least some of his power. Out came the pain wave, everybody took 20-some-odd points of damage, and then he teleported away. At which point the characters finally had an idea of what type of villain they were facing.
Andy: Well, some of us did. Others were too confused and just assumed everybody was a bad guy . . . a tactic which often paid off for good ol' Nat Mason, my barbarian-turned-drunken master.
Greg: Like that time you punched an old woman who just happened to be a polymorphed night hag. Grrrr. . . .
Andy: Nat Mason = Super. Genius.
Greg: When the threads of Ishinomori's master plan led the PCs through a fake crematorium to an abandoned, remote sanitarium-turned-undead factory to a storage house filled with zombies on the property of a major Island political power, they had their suspicions confirmed. Ishinomori had usurped a spot on the governing council AND threatened to unleash his zombie horde on the unsuspecting Island!
Andy: Which, we concluded, made him the bad guy. Good enough for me! One super-powerful shapeshifting magic-wielding crime boss, marked for a takedown.
But as far as long-term villainy goes, I think our high point was during my Bloodlines campaign In many ways, Bloodlines marks my personal high-water mark in D&D campaigns -- never before or since have I threaded together so many storylines, characters, and original content into a single campaign.
And perhaps the most significant thread in that campaign involved a group of archvillains who would, over the course of multiple years of play, dip their fingers into just about every kind of evil. Kidnapping, pillaging, heresy, treason, murder, slavery . . . you name it, these guys were into it.
Right from the start, I'd sketched out a general plan for this group. Mayhem and looting paid the bills, but they had big plans to unfold, and equally big grudges to settle with some of the folks the PCs trusted most.
As the campaign unfolded, the characters slowly gained awareness of the villainy that lay in wait. A simple kidnapping case provided the clue that something larger was afoot. Soon enough, a full-fledged slave ring (thought dead for a generation) had returned to the region. The heroes put this new group down, and even took out a couple of the masterminds, but three key figures -- the barbarian warlord Woldemar Skell, the mysterious blackguard Conallsson, and the sorcerer-lich Strabo -- eluded discovery. (I tempered that particular sense of loss by letting the PCs catch up with the vile kidnapper who'd started them on the case months earlier. See, closure!)
Greg: Our research into the slaver ring made us first think it was a copycat group, or at least the remnants of the once-feared Scarlet Sails. Legend said the leaders of that group -- including a sorcerer named Strabo, now apparently a lich -- had been killed a generation ago.
Andy: For the rest of the campaign, the shadows of that plot continued to plague the heroes. Even as the PCs found ways to thwart the plans of the remaining villains, at other times they became unwitting pawns of their worst enemies. They rescued the missing duke's younger son from Woldemar Skell . . . but only because Strabo had possessed the addled young man and wanted to spy on the royal court. They quelled strife between human and elven villages . . . but couldn't repair the political firestorm that destroyed a centuries-old alliance between the two races. They helped fight off a goblinoid invasion, but their absence from the city gave the villains the opportunity to get the duke's elder son exiled from the kingdom.
Greg: We just thought we had bad timing.
Andy: When it came time to replace the local bishop, the PCs threw their weight on the side of longtime ally Lorcan . . . unwittingly putting one of their greatest enemies in charge of the province's religious well-being. Even when they finally caught the wizard responsible for the human-elven strife (himself another unwitting pawn of the villains), they still couldn't prevent him from murdering the duke . . . which put Strabo on the throne in a time of near-war with the elves.
Greg: Strabo and Lorcan were classic D&D villains. At first we didn't know who they were, then we couldn't believe they actually existed, then we realized how powerful they were, and then we confronted them one at a time. Skell went down without much of a fight. When Lorcan, now bishop of the Western Province, revealed himself to be Conallsson (son of the blackguard Conall, one of the original slave lords), our deep faith in the church of Altius was shaken. When we finally determined Strabo was a body-hopping lich, we all but threw up our hands -- how do you kill something that can't be contained in one body?
Andy: The hunt for Strabo was actually one of the weakest points of the campaign. I'd unintentionally created a villain that the PCs couldn't beat, because they couldn't track him down. I hadn't been thinking far enough ahead of the plot, and when I ad-libbed the investigation, the PCs went down way too many dead ends. In hindsight, I should've spent more effort creating a "plot tree" for these sessions to ensure that the PCs -- and more importantly, the players -- could keep moving forward.
Greg: After lengthy investigations and several encounters with Strabo-possessed entities, we finally "killed" him.
Of course, he'd hidden his phylactery so well that his death was only temporary. He messed with us for another couple of weeks before we truly put him down and declared the threat finally over.
Andy: Can I just point out that one of the clues that led them to Strabo was the rotting corpse of a kidnapped woman that the lich had turned into a zombie for his own, um, personal needs? (Hey, you try being a lich who's suddenly in a living body for way longer than your fragile mental health can take and see what happens to you!) And that when the PCs finally busted down the door to his royal apartment, they also found a closet full of similar victims?
All together now: Ewwwwww!
(Honestly, I'm not really that guy. I don't remember exactly what inspired such a repugnant scene, but there's a good chance that Book of Vile Darkness helped.)
Anyway, by the time the PCs took down the last of the former slave lords (for the second and last time), they'd gained probably 15 levels since uncovering the first clue, and the end of the campaign was in sight. But even those final few sessions held echoes of the villains' plots and machinations, including a rock-'em, sock-'em no-holds-barred finale against the serpent god whose machinations had been driving most of the evil plots in the campaign, including those of the villains themselves!
As readers of my website probably know, I'm a big fan of villains. Fact is, they're often more interesting than the heroes who inevitably defeat them. If you're running a D&D game, you owe your heroes some memorable villains. Pull out all the stops, and don't hesitate to cheat. Hey, they wouldn't call 'em villains if they played by the rules!
About the Author
By day, Andy Collins works as an RPG developer in Wizards of the Coast R&D. His development credits include the Player's Handbook v.3.5, Races of Eberron, and Dungeon Master's Guide II. By night, however, he fights crime as a masked vigilante. Or does he?
As a D&D player, Greg Collins has been taking whatever older brother Andy can dish out for more than 20 years. Recently he took a seat behind the screen to exact his revenge upon his brother for killing his first character by washing him down a flight of stairs. In his time spent away from D&D , Greg is the events producer for magicthegathering.com.
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