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1. What is your favorite villain you ever challenged players with?
Caine is an NPC wizard originally written up in the Birthright campaign setting (circa 2nd edition AD&D). He's described as a wizard who exchanges spells and magical protection to the ruler of Endier, where his tower resides, in exchange for military protection so that no one attempts to raid his tower. From this brief description, and his listed alignment of Neutral-Good, I envisioned him as a benevolent wizard hoboing about the countryside and occasionally bumbling his way into other peoples' problems and helping them out, Doctor Who style. In the expansion material for the country of Endier it describes Caine in more detail, but for the campaigns I ran I only used the description as a vague idea of what the public thinks Caine does.
I always introduced Caine as a helpful wizard for the PCs to be doing "good works" around the countryside. His stated intentions were always to protect the status quo of Endier's independence, and if this meant assisting a group of mercenaries with some helpful magic to get their jobs done along the borders of Endier's neighbors then he would be happy to oblige. In truth, Caine viciously eliminated any rivals to his own power and always used subordinates or underlings to do it. If somebody's guild or temple was moving into a region where Caine held power he would immediately find ways to portray them as bad people and try to keep them disorganized and ineffectual. Caine's stated objective of maintaining the status quo was still pretty accurate, but it was his power base he wanted to maintain, not Endier's.
In practice, this meant that Caine would appear to the PCs occasionally and give them information that was just false enough that on the surface it seemed true but deep digging would reveal the deception. This information would always send them off on some personal quest or vendetta to stop an interloper or destroy or corrupt organization. I always expected that as Caine's lies would become more elaborate and easier to see through the group might begin to question him more openly or confront him but no, they would continue to work for him and nobody would ever question his stated motives even when he took magic items away from them (that he thought they shouldn't have) or lavish them with gold coins (which he didn't need but had in abundance), probably because the players would believe wholeheartedly in the trope of the helpful wizard.
2. What is your favorite organization behind wrong-doing in your setting?
The Northern Imperial Temple of Haelyn. Birthright again.
The setting tried to use mortals squabbling over religion as a theme, and it didn't always work because of the way AD&D structures the way clerical spells work, but I still embraced the concept of warring churches and infallible priests. The Northern Imperial Temple (NIT) were fascists and fanatics and would not accept the worship of any other deity before the worship of Haelyn, the Patron God of all Anuire. Their influence had spread to other countries in the region and they fought openly with some of their neighbors, and fought deceptively against some of their distant rivals. The NIT used doppleganger assassins whose sole purpose was to remove anybody whose influence was spreading into the NIT's home or ally territory. A major theme of my Birthright campaign was a large-scale multiple country war that was started by a minor noble being assassinated by a doppleganger that worked for the NIT.
3. What is the most interesting location you ever staged a battle in?
Inside a pocket dimension shaped like a 4-sided die where gravity pushed outward. There were fleshy tendrils rising from the center of each of the four sides which met to a small meaty sack in the center, and inside the meaty sack was a sleeping demi-goddess. Wolves made of shadow prowled the maze on the surfaces of the dimension's walls, and a constant storm pulsed around the center of the dimension with random lightning bolts and fireballs.
Either that, or a tavern.
4. What is the most interesting chase scene you ever had in a game?
A PC assassinated another character, an NPC, in broad daylight in a bustling city's dockside harbor. The NPC's personal guards, as well as city patrolmen, chased the PC through the dock and into a marketplace and then up onto the rooftops of the city. It was a brief, exciting and intense scene, with the player announcing he would jump across a horse or stab a guard in the leg in order to get away from his pursuers. He was never caught.
5. What is the most evocative scenic location you have used in a game?
The Spiderfell, from Birthright again. Probably. I ran a Planescape game a long time ago, but none of the settings I used stick out in my memory. Taking players into the Spiderfell was something I relished and still remember. The trees had grown to incorporate spiders in almost every aspect, the goblins who hunted the forest bore spider-like features, and the oppressive darkness of the place was fun to describe. Nobody ever wanted to go very far into the place, and very few ever ventured farther than a few trees.
6. What is the most interesting one-of-a-kind unique monster in your games?
Imagine a centaur, but instead of a horse the bottom half of the creature is a mountain goat, and instead of a human head it's an eagle's head. They are wild, feral creatures who will attack anyone for the meat on their bones, but are also mesmerized by magic and will attempt to kidnap anybody who shows a display of magic in the hopes they can learn this arcane art. A failure to communicate or an unwillingness to teach magic means the kidnapped will eventually become dinner.
I never came up with a name for these guys. I never come up with names for most of the things I create. I just called these guys eagle-centaurs. Eagletaurs? Nah.
7. What is the most tantalizing artifact, relic or tech you have ever used in game?
The Dragon's Amulet. I ran Birthright three times and I used it every time. It's an amulet split into pieces that gets more powerful as the pieces are brought together. It can detect dragons, it can protect the wearer from flame, it can allow you to speak draconic languages, it can regenerate flesh. It can do a lot more but nobody ever managed to get all of the pieces. Oh! They looked for them, but they never found all of them. As the pieces become stronger, they begin to pull nasty things toward the owner. Rabid dogs. Hungry goblins. Lizardmen. The longer the owner has a piece of the Dragon's Amulet, the stronger the pull gets and soon creatures are showing up almost every day looking for a little piece of ceramic that never chips and never breaks.
8. What is the most world shattering thing a player has ever got up to in your settings?
Birthright again. The one time players ventured deep into the Spiderfell, I designed a dungeon for them to explore. The Spider is a powerful hundreds-of-years old monster who resides deep within the Spiderfell, and I gave him a lair. The PCs managed to work their way into his throne room under the pretense of a parlay and then fought him. He tried to escape as his flesh succumbed to their spells and weapons, but he was too slow and they killed him. One player stole his Bloodline and another kept his body in a bucket to make sure it would never regenerate back to life.
9. What is the strangest death of a character in game you have run?
Nobody has ever died in a strange way. They were always predictable affairs, except the time I rolled a random encounter for a pack of jackals in a swamp and a group of low-level characters were overrun by the pack with a TPK. That was pretty strange and unexpected. Also, very unsatisfying even for me, I've never used random encounters since.
10. What is the most intriguing challenge, trap, or non combat obstacle in your games?
The NPCs. The players either never spend enough time learning an NPC's true motives and they get blindsided by their actions, or they simply underestimate the NPC in some crucial way.
11. What is most interesting ability or character option you have added to your game?
I've always allowed players to have their characters start with dark powers from a secret pact with a demon or similar malevolent spirit. No takers yet.
12. What is the strangest mash up or weirdest system hack you have made in gaming?
My third time running a Birthright setting I used World of Darkness rules with my own added houserules for playing elves, dwarves, halflings, wizards, and/or clerics. I also had to write up how Bloodlines worked, which wasn't that hard, but getting the rules for how Bloodlines grew and gained power were difficult to keep as a slow progression. The game lasted for over a year before the group split due to players moving so I must have been doing some things right!