The Shadowdarkening Drawtober 2024

I've been doodling away for a while now, enjoying getting back into the flow of creating nonsense art and illustrations, mostly inspired by the Shadowdark roleplaying game. This month the Shadowdark crew are running an art challenge across their social media so...good timing I guess!

I'm planning to get involved (on various fora), posting one themed image a day, according to this.

So, here we go.

Day 1 - Torch

This illustration is intended as a 'filler' for text in the Shadowdark adventures I'm writing (available here under 'Red Boar Games'). It represents a fantasy adventurer's pack, set down while they rest on their travels.

Day 2 - Saint Terragnis

St Terragnis is a deity int he official pantheon of the Shadowdark game. the brief destription paints her as a goddess of justice and noble conflict, so I figured a sort of 'Joan of Arc' figure ould fit the bill.

Day 3 - Its a trap!

This trap has an adventurer tumbling down a tunnel full of rollers. It comes from my memory of some of the earliest Dungeons and Dragons games I played. I've reused it in adventures since then.

Day 4 - Dungeon

Quite a vague term to try to depict, so i went with a classic 'dungeon door', the sort of thing you'd find at the entrance during a fantasy game.  Of course the text comes from the classic Inferno by Dante Alighieri, and is fitting for such a dark and dangerous place!

Day 5 - Orc 

This one's an 'old school' pig faced orc for the earliest days of Dungeons and Dragons roleplaying.  Older players like me still look back fondly on these origins and the 'orc' as a monster has taken on many different forms. Its an homage to Charles Hildebrant's classic art.

Day 6 - Shadowbarge

In the early days of the shadowdark RPG, product shipping was somewhat delayed leading to the 'Shadowbarge' meme of waiting for a delivery.  This inspired me to a rather unsubtle depiction of an adventurer waiting for a ship.

Day 7 - Skeleton

The classic monster in roleplaying games is the undead skeleton threatening the living.  I like drawing decrepit subjects like this.

Day 8 - Darkmantle

This interesting monster from Shadowdark is similar to monsters from other games, but plays well into the rules of the game, where light sourches like flaming torches or lanterns are essential. the Darkmantle can turn those lights off which is terrifying to the adventurers who then have to fight this foe in the pitch black! MY players encountered a mob of these floating gribblies in a game a while ago. I drew this afterwards, and when I showed it to them one said, "how is this creepier than the actual one we fought?! I was definitely picturing a very unthreatening umbrella like monster. But this is horrifying!" Hehe...

Day 9 - Wizard

The all time favourite character class for fantasy roleplaying. This one is a kind of mix between Terry Pratchett's Rincewind character and my image of Jack Vance's classic magic users from his Dying Earth novels.

Day 10 - Minotaur

A classic from Greek mythology of course, but this one is my rendition of the big bad monster in the Shadowdark 'Caverns of the Crimson Minotaur' adventure.

Day 11 Hex

Another wonderfully vague term open to interpretation.  I thought about this for a good while, before settling on another illustrative 'filler' image.  This time focussed on the sort of paraphenalia you might associate to dark 'hex' magic. I like drawing skulls and bones, a callback to a previous career of mine.

Day 12 - Ramlaat

Ramlaat is another deity from Shadowdark's pantheon. 

'Ramlaat is the Pillager, the Barbaric, the Horde. Many orcs worship him and live by the Blood Rite, a prophecy that says only the strongest will survive a coming doom.'

I therefore drew it looking a bit like the sort of god that pig orcs might worship.

Day 13 - Stingbat

Stingbats are the Shadowdark version of a fantasy monster known as a 'stirge'. A bizarre cross between a bat a dragonfly and a mosquito they are jolly little horrors.

Day 14 - Tome

Books have been an essential part of my live since I was old enough to pick one up. My grandfather took me to the local library once a week for my four books. I married a librarian. So simple image of a tome is all that's needed here. Of course it needs a little homonculus to take an interest in whatever esoterica those pages contain.

Day 15 - Hammer
So many options for this keyword, but a simple object left after it smashed the skull of a long dead opponent will do.

Day 16 - Slime

In fantasy roleplaying games a common enemy or monster type is the 'ooze' or slime, a sort of wierd puddle creature of living goo. They are often able to move over walls and ceilings, and form pseudopoda to attack its prey. This rugged dwarf warrior has found one such ooze.

Day 17 - Priest

Another classic fantasy roleplaying class, the priest or cleric is a holy warrior able to use divine magic and power to heal their allies and harm their foes.  One common power is the ability to drive the dark undead back to the shadows, turning them away or sometimes destroying them with divine force.

Day 18 - Witch

Well, it'd be rude not to lean into the stereotype on this one! Slightly cartoony this one, she's clearly out looking for her cat. the damn thing is always going missing.  

Day 19 - Oracle

I went literal with this one and based it on representations of the Oracle of Delphi in classical art.

Day 20 - Wraith

Wraiths are incorporeal undead, like ghosts, which is tough to represent in ink!

Day 21 - Hag

In fantasy roleplaying games hags are dark creatures, usually respresented as crone like monsters.  I leaned into the dark witch kind of imagery with a bubbling cauldron.

Day 22 - Crypt

I think this one is more of a mausoleum than a crypt but its quite a common encounter in fantasy roleplaying games. The adventurers stumble on a burial chamber which usually has some surprises in store.  I tried to draw a zoomed out view here, representing the commonly used 'grid pattern' of many game maps. Clearly this adventuring party have a disagreement on how to proceed with this situation!

Day 23 - Thief

So many options! But I went back to the archives with this and drew an homage to an old AD&D classic by David Trampier, a prolific early artist in the hobby. My drawing is inspired by this masterpiece which defined the early 'thief' character class.

Day 24 - Kobold

Kobolds are common lew level enemies. Their nature has changed over the years, but I always see them as creatures tied to the dragons in the world you're playing in.  Commonly chaff to be butchered through, some like Tucker's Kobolds can be more of a challenge!

This little chap is clearly just chilling out, enjoying life.

Day 25 - Whisper

I went literal again ans simple depicted a whispered conversation. What are they whispering about? Who knows?

Day 26 - Devil

So many options here but I stuck closely to Shadowdark description, which is fairly traditional.

Day 27 - Gauntlet

Another keyword with many possibilities. I went with s simple image of a gauntlet, but wanted to add a bit of mystery or nuance, so had this poring through a tome.

Day 28 - Crawler

In the Shadowdark game, an adventurer is referred to as a 'crawler', a play on the temr dungeoncrawler I think.  I also took it literally and had the character crawling through a tight space!

Day 29 - Gold

I could've just drawn a pile of gold coins. But I felt something a bit more interesting would be good.  I was going to take inspiration from another David Trampier classic. Instead I took a similar inspiration from the 'suitcase' scene from Quinten Tarantino's Pulp Fiction. I tried to be inspired by the framing of the actor rather than give a literal copy of him.

Day 30 - Potion

Not every potion in roleplaying games does exactly what the character thinks it will. In this case the party's wizard got slightly more than he bargained for! Lets hope the effects wear off soon.

Day 31 - The Arcane Library

So, here we are at the end.  The Arcane Library is the company that produces the Shadowdark RPG, writting by Kelsey Dione.  So what better wahy that to combine this all together with a mystic writer under the Arcane Library icon, in a small library room? 

So there we are, all done! It was a lot of fun drawing these images, trying different things, and illustrating to a very vague brief. I'll defintely be carrying on with my doodles!