Freelance Murderthieves

datetime April 18, 2017 12:01 AM

Toward the end of 2016, my long-running Pathfinder group got bored with our campaign and decided to try something else. We’d been interested in dipping our toes into 5th Edition D&D for a while, just to see how the game had changed, so my associate, Rich, volunteered to run the first published campaign, which is titled “Something Something Dragons”.

I’m pretty sure that’s it.


D&D characters are basically the only things Spud enjoys drawing, so I’ve spent the past month giddily scratching out illustrations for our four brave looter/arsonists. And because I knew I would need to squeeze a blog article out of the exercise, I recorded the colouring process to produce time lapse art videos set to thematically appropriate music.

So, let’s meet the new family!

The Retired Conqueror

Like all of Spud’s RPG characters, this one has a long backstory. Don’t expect the same from the other ones, as Spud’s friends aren’t anywhere near as long-winded. 😛

The Dread Helen spent decades at the head of a merciless horde of mercenaries and barbarians, conquering everything from fishing hamlets to small nations in a vain effort to sate her endless thirst for battle. Each time she brought a city or empire to its knees, she would rule it for a brief period before becoming bored, at which point she would name one of her innumerable children– usually fresh out of the womb– as its new tyrant. This cycle of conquest and heredity spiraled on for over forty years, with Helen never once bothering to revisit her old holdings. Eventually, on one drunken and introspective evening, she took stock of herself and realized that she had somehow avoided death in battle for long enough to become an old woman. Deciding that she had carved a large enough wound into side of the world, Helen abruptly stood up and walked off over the mountains, leaving a stunned horde behind forever.

Helen intended to live out her days on some snowy peak, growing fat on bear and mead, but fate had other plans. As she poured her breakfast one late morning, Helen was surprised to see a lone figure walking up the mountain path to her shabby fur tent. Helen drew her blade, but the fellow surprised Helen by dodging her swipe and capturing her in a… hug?

Helen was confused.

Tears of joy welled in the broad man’s eyes. He gushed that he had looked forward to this meeting for his entire life. He was her son, left behind to rule the kingdom of Strahj when she departed nearly four decades past. The terrified nobles raised him to rule, but when he came of age, he decided that he did not want to be a king. Like her, he named a child successor, and marched off to seek his own fortune.

He found the life he sought in a neighbouring country. He fell in love with a brown-haired girl, and learned the trade of millinery from her father. They had three daughters, and lived happily. As he neared his fortieth year, though, he grew sad that in spite of the good life that he had made, he had never known the mother who inadvertently led him to it. He spent three years searching for her, retracing her steps from conquest to conquest. He met many of his siblings, and was delighted to learn that most had followed his own path, turning away from power to live simple lives. Eventually, after many years on her trail, he learned of her retirement from a fat old dwarf who had been part of her horde, and marched up her mountain to meet the mother none of them had ever known.

The boy hugged the stunned Helen close as he wept out his joyous tale. When he was done, he released her, and beamed the innocent smile of a lost son to his mother.

Helen paused for a moment, her eyes wide.

Then she screamed.

And the boy fell in three pieces.

Helen stood there in the snow, coated in the blood of her blood, breathing rapidly as her own sense of peace and accomplishment, hard-won through a long life of endless war, withered away. Was this the mark she had left? Did the world know the Dread Helen not as a mother of tyrants, but as a wellspring of thatchers and tailors? Come to think of it, did it know her at all?

It couldn’t be. She had killed too many, burned too much. This one was weak, but the others surely held three continents in their grip. He lied, or was too simple to understand.

It wasn’t possible.

She had to know.

Helen pulled her armour from the old rusting chest, left her morning’s kill in the pink-stained snow, and very nearly flew down her mountain. She killed a trader and cut a stout horse free from his wagon, then galloped to the nearest city-state she could remember butchering, some two decades past. She rode into town and straight to the keep. She leapt from her steed to cut down three guards too stunned to react, then carved a red path to the throne room to speak with her daughter.

She found her. Helen had never seen her own face in a mirror, but this girl shared many features of the face that Helen had ordered carved into statues and mountainsides. Somehow, though, the features were softer, more delicate, and happier on this face. She had Helen’s broad shoulders and silvery eyes, but bore a smile that had never marred Helen’s scowling face.

However, the girl was not in the throne room when Helen found her. She was in the garden, planting blue flowers with fingers stained earthen-black. And when Helen appeared, dripping with pieces of guard and peasant, the girl was only momentarily shocked before an even broader smile spread across her face, and she ran toward the mother she had always known would come back for her.

Helen had learned from the last encounter, intercepting the hug with a kick before bringing her mighty blade down on this beautiful disappointment.

As more guards poured out of the castle, Helen knew that she would not return to her bear-skin tent on the mountain. Few years remained to her, she knew, but it was clear what would fill them. Throughout innumerable lands, the weeping wound carved by the Dread Helen had scabbed over with kittens and rainbows. She had torn through the world on a tide of fire and steel, but had left behind her only a trail of happiness, contentment, and failure.

Helen’s vision clouded red as the horror swept over her.

She had begotten only weakness.

But she had time yet to correct the mistake.

Helen absent-mindedly butchered the last of the guards, then sauntered off to find her horse.

There was no time to lose. She had filled the world with failures, but she still had enough strength in her old bones to clean up the mess.

Helen is a horrible, hate-filled old woman, so naturally I based her likeness on Paula Deen. I imagined that her armour would have been assembled from multiple sources over a lifetime of pillage, so I made a point of mis-matching as many cloth and armour layers as I could manage. The only nice-looking piece in the hodgepodge is her treasured breastplate, adorned with the face of her first husband, a Beholder named Greish. Even this, however, she has reinforced with extra armour plates and an array of probably-useless but nonetheless intimidating metal spikes.

The Dread Helen is my second-favourite D&D character and one of my favourite drawings that I’ve ever made. I’m unspeakably pleased with how she turned out, and if Rich kills her I will BURN HIS GODDAMN HOUSE DOWN.

That or cry.

It’s hard to say until it happens.

The Diffident Crusader

The other three party members have little or no formal backstory, but I did my best to work with each player to draw out what they imagined their character looked like and how they might decide to dress.

Ea here, played by Kevin, is a Tiefling Paladin. Paladins are passionate crusaders for good sworn to serve a god or an ideal, and during our first session, Kevin declared that Ea served the god Helm, patron of guardians and protectors. Then we took a two-month break because people’s schedules suck, and when we came back, Kevin retconned and re-declared that Ea served no particular god and no particular philosophy. She was just a stern lady who protects people.

With, yaknow, magic beams of holy light. That she draws from apparently nowhere.

Goddamnit Kevin. ~_~

This left me without much to work with on the concept front. I tried to resolve this impasse by designing her in a badass suit of Paladin plate armour, but Kevin nixed this idea, saying that she was very simply dressed in basic chainmail and leather.


I struggled to make anything out of his description for weeks, but for the life of me couldn’t make “paladin of nothing dressed in level 1 starting gear” look interesting. However, after weeks of agony, Kevin accidentally solved the problem.

“Just make her look like Ronda Rousey.”

I… can work with that, actually.

I don’t think the likeness turned out very well in this case, but it gave me enough of a foundation to build on. Because while it may be tough to imagine what sort of outfit Ea, Paladin of Ehh I’ll Decide Later would wear, it is somewhat easier to piece together the battle garb of Ser Rousey, Paladin of Beating the S*** Out Of People.

The Pointy Punchsmith

And then there’s Jay.

Jay is hard to adequately describe. He’s quiet, and he hates science fiction, and no matter what campaign we run, he always plays something like an elf, and always plays something like a ninja. Jay knows what he likes, and he will find a way to make it happen.

I admire that sort of philosophical certitude.

This time around, Jay’s particular avatar of the God of SmoothPrettyPointy Martial Artists is Rolen, a wood elf monk who punches kobolds for justice and harmony and all that nice business.

By this point in the exercise, I had figured out that all of the characters were going to be based on celebrity caricatures (though with the understanding that I’m not actually very good at drawing likenesses). However, it was impossible for me to imagine Rolen as anyone other than Jay himself. Rather than fight against this, I went and dug up the only photo of Jay I had access to, which was a 20-year-old picture his wife posted on Facebook.

D’awwww. 🙂

That was basically all I needed to get started. 😀

I did not, in the end, manage to make the character look anything like real-life Jay. Rather than admit to my own shortcomings, however, I choose to believe that Jay’s inherent jayness is ephemeral and impossible to capture in a still image.

It was an act of bald hubris for me to even make the attempt.

The Nautical Huckster

Oh, and Tom was also there.

He was playing a dwarf sorcerer called Farg Beardpickle or Forvorgen Stonewhangle or some other godless abomination of a name, and he wanted it to be a pirate because Spud hates pirates and Tom is an asshole.

We worked out a backstory wherein Floorgrim Bojangle had been captured as a slave following the Dread Helen’s one ill-fated attempt at a naval battle (after which she cut her losses and declared the seas unworthy of her rule). It turned out that the unassuming little dwarf had a skill for resource management, and became the horde’s de facto accountant and quartermaster for over a decade, ensuring that everyone was fed and paid and that their captured booty was accounted for. On the rare occasion where Helen deigned to purchase goods rather than take them from the corpse of their former owner, she would simply grunt to Forgegrain Bonedangle to “Pay the man!” and walk off, as Helen had absolutely no interest in keeping track of any of her own vast wealth.

Floorplan Belljingle realized very quickly that his employer’s disdain for material goods meant that he could pilfer as much of her treasury as he liked and she would never notice or care. As a result, Foreboding Darkjungle spent the last eleven years of the Helenic Horde’s existence siphoning gold away and stashing it in dozens of caches across three continents. After the horde disbanded, he was free to travel around collecting his booty, consolidating it within a massive ship that he had built to contain it.

Fellreaver USBDongle had nearly completed his task and was all set to begin enjoying his retirement, when out of nowhere, his supposedly retired boss came stomping back over the horizon and informed him that she had a new quest that he would be helping her with. Too terrified to argue or run, Floopdewhoop Balljuggle simply whimpered and jogged off after her, hopeful that whatever nonsense she was getting up to could only last for so long before fate caught up with her, freeing him up at last to sail off with what he now regarded as his rightful property.

It’s John Ratzenberger.

As a dwarf pirate.

Let’s not cheapen this with words.


Click to embiggen

And now, after a series of unlikely inciting events, our four heroes are running around the world, trying to resolve a series of dragon-themed contrivances with violence and polyhedra.

It’s going pretty well so far.




2 thoughts on “Freelance Murderthieves

  • horrid74

    Love the backstory for your character. Have you ever read A Crown of Cold Silver? This is a great variation that really made it your own. Awesome character concept!

  • Captain Spud [Post author]

    I don’t read much fantasy fiction, outside of Ice and Fire and Discworld. Helen was primarily inspired by Cohen the Barbarian. 🙂

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