Putting this as a comment!
I just really thought writing about the lore behind the paintings would be fun.
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Obligatory Lore Behind the “Paintings” (1029 words):
In which Crackerjack tries to pick up a paintbrush.
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Colby “Crackerjack” Cutlass was 7 years old when he first picked up his dagger.
He was 29 when he first lifted a paintbrush. And as far as he was concerned, the dagger was more his art form.
He sat on his stool, brush balanced awkwardly between his thick, calloused fingers. Before him stood an easel holding an almost finished painting, one he’d spent most of the afternoon on. His hand shook a little as he attempted to add another detail, and after several unsuccessful strokes (of which he was increasingly starting to realize that the more he tried, the worse it got), he finally tossed it into the water cup with a CLINK and ran his fingers through his hair with a defeated groan.
He’d been trying to paint himself and his younger adopted brother, looking every bit the fearsome warriors they used to be. Instead, they looked like two awkwardly proportioned scarecrows trying so hard to look cool that they circled back around into looking lame. A child could’ve done it better.
Crackerjack rubbed his face, smearing dried paint on his cheeks.
Like, honestly…
He should just throw it away and forget about it. He wasn’t born with the talent for this. Just how in the gosh-darn world did people even DO this so well?!
“This is freakin’ awful.”
“Qu’est-ce qui est ‘awful’?”
Crackerjack looked over his shoulder.
Zeke “Stendhal” Cutlass stood behind him, holding a small tray of various cut-up fruits, meats, and cheeses. Crackerjack hadn’t heard him come in.
“Me. Apparently.” Crackerjack said as smoothly as he could manage.
Stendhal tilted his head. “What are ya’ doing?”
“Painting.”
“Ouooh? Whatchu paintin’?”
“Uhm. A thing.”
Stendhal hummed and approached, leaning over his brother’s shoulder to inspect the canvas. For a few moments, he was quiet. Crackerjack watched him expectantly.
Then Stendhal pointed. “Is that s’pposed to be a broomstick?”
Crackerjack slowly turned his head. “…Excuse me?”
“That thing there. That long brown one. Is it’a broomstick? Or a feather duster?”
"That’s you, stupid.”
Stendhal’s eyes widened. “Oh.”
A few awkward seconds passed.
“OoooOOOH! I see it now!” Stendhal scratched the back of his neck, suddenly looking rather sheepish. “Well, now that ya’ mention it, I can see the resemblance! That really does look like me. Good job!”
Crackerjack gave him a look. “You’re not saying that to make me feel better, are you?”
“What? No!”
“Stendhal…”
“I’m serious, Crackerjack! I think it looks good.” He pointed his chin towards the badly painted rendition of himself. “Looks kinda cute, actually!”
Crackerjack groaned. “Forget it.”
Stendhal chuckled, but his smile faded when his brother didn’t join him.
“…Crackerjack?”
When Crackerjack said nothing, he slowly placed the small tray down.
“Sorry… I just—I figured I’d drop by and give you a snack; I didn’t really mean to—”
“It’s fine. You’re fine.”
Stendhal didn’t look convinced.
Crackerjack stared up at the ceiling. “Wanna know something? I’ve done… so many, many terrible things as a pirate. And I don’t really know anything else to do outside that.” He looked toward the canvas. “Thought maybe it’d be nice to make something for once. Something that didn’t involve hurting anybody. But this…?” He gestured helplessly toward the canvas. “This is something else entirely.”
Stendhal said nothing.
“There are kids half my age who can paint things that look like they ought to be hanging in some rich bastard’s house.” He looked down at his hands. “Look at me… I’m pushing thirty now, and I thought doing this would be easy, but now that I’m here with everything I need to do it, it kinda feels pointless to even try.”
“Why?” asked Stendhal.
“Why what?”
“Why d’ ya’ think it’s pointless?”
“Because I’m awful at it!”
“So?”
Crackerjack looked at him incredulously.
“You’re terrible at it,” said Stendhal, “so what?”
"So I should quit.”
“No! nonononono!” Stendhal waved his hands. “Just—Just listen to me for a sec! Riddle me this, Crackerjack, what’s the point of ART?"
“…Making pretty things?”
“And?”
Crackerjack stared at him.
Stendhal looked at Crackerjack’s painting. *“*ART is about showin’ people how ya’ see things! Least, that’s how I see it. Everybody sees the world differently, don’t they? Ain’t much point in makin’ art if everybody’s makin’ the same thing.”
Crackerjack raised an eyebrow. “And your point is…?”
“Lookit this,” Stendhal said, pointing at Crackerjack’s painted face. “Your face is a bit… well…”
“Ugly?”
“Uh… I was gonna’ say… interesting.”
“How generous.”
“But look at ya’ painted your weapon!”
Crackerjack followed his finger.
“Ya’ got the hilts, and even the little nicks along it. You’ve really got an eye for detail,” Stendhal winked and flashed his lopsided smile. “Ya’ even got my missin’ tooth!”
Right… Now that Stendhal mentioned it, they did look a lot more detailed than everything else. Crackerjack had spent nearly an hour getting his dagger’s shape juuuuust right, carefully painting every scratch and blemish. He knew his dagger just as well as he knew himself.
Stendhal continued. “You’ve spent your whole life around weapons. I don’t think I know anybody else who knows what they look like, how they feel, and what makes one different from another more than you do, and it shows!”
Crackerjack said nothing.
“That’s a part of you, isn’t it? Weapons… And all those years you’ve spent sailing around the War Seas… Crackerjack, you’ve seen things other artists could only imagine, so why not paint those?”
Crackerjack frowned. “You’re saying I should just paint the things I know…?”
"Yeah! Whatever you know. Maybe people aren’t your thing. So what? Doesn’t mean you’re no good at painting. Quick! Tell me someplace cool you’ve been to before!”
“Ehrm… Ravenna?”
“Yeah?! And what cool thing did you see there?!”
“Blasted Rock. But only from a distance…”
“Aha! There’s your next thing to paint.”
Crackerjack looked at his painting of himself and Stendhal, then at a small pile of empty canvases and paints in the corner of the room (Stendhal and his girlfriend, Vivian, had graciously gifted him everything he needed for his birthday a couple of weeks ago). He was quiet for a long moment before saying, “Suppose I could give that a try.”
"Yay! C’est ça, l’esprit!" Stendhal pushed the plate of fruit, meats, and cheese toward him. “Now eat up! Can’t expect to get to work if you’re runnin’ on an empty stomach!”
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Thank you for reading!