• Published 3rd May 2016
  • 758 Views, 72 Comments

Woebegone - Lost_Marbles

The embodiment of bad luck comes to Ponyville, and anypony foolish enough to cross his path meets disaster. And he's very sorry.

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Chapter 1 - Something Unlucky This Way Trudges

A loud groan echoed throughout the halls of Twilight’s castle and into her ears as the floor beneath her shook. All of the books on the table in front of her slid to the right, as though they fell victim to an invisible force. Now, Twilight was a self-proclaimed expert on books, and she knew for a fact that books didn’t move on their own (no matter how alive some of them may seem), so something was definitely up -- or down, as the case may be. Books slipped off the table and plopped on the floor. Her tea saw its friends jump off the cliff and went to join them.

“No!” Twilight shouted and grabbed the tea before it could spill. Twilight had solved one of her dilemmas. Now she only had about a dozen more to go. All around her in the throne room, vases tipped over and rolled to her right and smashed against the walls. Banners and curtains all at once leaned toward the same wall the smashed vases collected on. Up above, the memory stones that hung from the chandetree intertwined and tinkled like a windchime.

“Twilight!” Spike clawed his way on the inclining floor down a hallway and through the door to the Element of Harmonys’ throne room. “What’s happening? The castle’s turning upside down!”

“I don’t know, Spike. I-- ah!” Her grip on the crystal floor gave, and she slipped down toward the dragon. She fanned out her wings to catch herself in mid-tumble, but it was too late. A wing smacked the door frame and knocked her off center. She collided into Spike, and the two tumbled down a long hallway, bouncing off of pillars and stairs and each other until they crashed through a window and landed on the grass with a thud. Luckily for Spike, she was able to break his fall with Twilight’s spine.

Spike climbed off Twilight, who moaned in pain and looked at the castle with its new slant. Tilted at a mere 45 degrees to the side, the whole right side of the castle was sinking into the earth. Twilight picked herself up and saw Spike getting a closer look at the hole. “Oh no! The foundation is crumbling! Spike, get away from there. We’ve got to evacuate the area before anypony else gets…”

A scream echoed throughout the castle and grew louder before Starlight Glimmer tumbled out of the same window. She fell with a thud on top of Twilight.


Starlight groaned as she crawled off Twilight. “Eh-heh. Thanks for breaking my fall.”

“No problem,” muttered Twilight as she rubbed her heroic, selfless spine.


“Thank y’all. Come again.”

Out in the marketplace, Applejack was selling her produce. Everything was going so well that the farmpony believed that nothing could possibly ruin her day. She smiled as she slipped the bits on the counter into her apron pocket. Today was especially profitable since Lyra had decided to set up shop next to her, and by “shop” she meant that she sat on a bench and played her lyre for the foals as the parents shopped about for their groceries. The parents were particularly happy for the distraction and would buy apples for themselves and their children as the foals danced about and listened to Lyra sing before continuing on with their errands. Perhaps Applejack may have to consider making this a regular thing. Her apple pies, apple dumplings, and apple fritters had almost sold out, and it wasn’t even lunch time. She was so happy that she had invested time into making a new wooden, wheeled stall with wider compartments to hold more goodies and keep them warm. She even admired the new sign on top that Pinkie had painted for her. The wooden sign was eye-catching and made her stall stand out even more than usual. She resisted the urge to puff up in pride, but how could she not feel like a million bits with her hard work paying off immensely? That was when the whispers stole her attention.

Applejack looked up and saw a lot of ponies clearing themselves from the center of the street as a slumped being dragged his heels through the town. Wrapped in a raggy, patched-up jacket and wearing a large top hat, the poor creature trudged his way towards Applejack’s stall. Above him was a small but menacing thundercloud that would occasionally flash and let out a small rumble while pouring rain on top of the downtrodden bum; in a useless gesture of defiance, he held up the broken frame of an umbrella. No cloth or plastic was on the bent and crooked metal skeleton to protect him from the punishing rain. With his eyes to the ground in front of his two-toed feet, the bipedal being’s face was hidden underneath the large rim of his oversized hat, but his matted red hair flowed all over his shoulders and down his back.

Dread filled Applejack as the bum approached without slowing its mired pace. Then, almost without warning, the ground crumbled into a hole at his feet, and he fell in face first. There was a metallic clang. Ponies trotted in place, unsure if they should give him aid or stay back. When no help came, a small green hand came up out of the opening, then another with an umbrella frame, and the bum pulled himself up. He muttered something under his breath and continued towards Applejack’s stall. Behind him, a small jet of water streamed up from the ground, as if a new fountain had sprung up in the middle of the road.

Once he was a considerable distance from the hole, ponies rushed up and looked inside the hole. “Goodness gracious,” said one. “He fell right onto a septic line.”

“And it’s leaking!” said another.

“That’s a huge dent!”

Applejack blinked, and there he was right in front of her. From underneath the large rim of the hat, two sunken, tired eyes looked up at her. The guy spoke in a quiet, defeated voice, “Can I buy something to eat, please?”

The pitiful voice plucked Applejack’s heart, and she couldn’t bring herself to respond as she took in every detail of the pony--er--being in front of her. Large, sad bags sagged under his eyes. Wrinkles trailed down the side of his large cheeks, and his tiny button nose sat on the center of his wide, droopy face. A four-leaf clover was stuck in the band around his large top hat, and it too slumped with exhaustion.

Before she could say anything, the little guy pulled out a coin bag from under his coat. It was a patchwork of different colors and patterns, and when he reached in to pull out a few coins, the bottom tore, and his bits spilled on the soakened ground beneath him.

“Oh no, not again,” he muttered as he got down on his knees and picked up his bits.

Applejack couldn’t stand the sight of it. She rushed around the stall and picked up bits alongside him. All the while, the poor guy apologized profusely for causing Applejack so much trouble, which she just as wholeheartedly denied. It was no trouble to help. He apologized for making her get up from behind the stall. She countered saying that it was an opportunity for her to stretch her legs. He apologized for getting her wet. Applejack replied that under today’s brilliant sun, she’d be dry in no time, and therefore it wasn’t a problem. Then he apologized for apologizing so much. Applejack told him to settle down.

Then he apologized.

With the bits collected and put up on the counter, Applejack resumed business as if nothing happened and as if there weren’t a large crowd of gawkers watching. She pointed to all of the goods she had available on her stall. “What’ll ya have?” she said with the cheeriest smile she could muster, hoping that her quality customer service would at least cheer up the bum, if even by a smidge.

The guy looked at all of the sweets and apples on the stall. “Oh, nothing much. Just an apple, please.”

Applejack nodded and took the two juiciest, plumpest apples she could find out of a basket and placed it in front of her customer before sliding one coin to her. “Here ya are, sugarcube.” The guy blinked at the second apple before looking up at Applejack. Before he could correct her, Applejack said, “I’m selling two for one today.” To admit she had given him a second apple out of pity would be rude. She didn’t want to offend this poor fella. Hopefully none of the other ponies behind him had heard her say that. “Limited offer,” she added for extra measure.

As the hobo was putting his remaining coins in one of his coat pockets, Applejack tried to start a conversation. “So, what’s your name, sugarcube? I’m Applejack of Sweet Apple Acres, home of the finest apples in all of Equestria.”

The fella looked up with a small smile slowly spreading on his lips, but it quickly disappeared. “Oh, you don’t want to talk to me. I’m bad luck.”

Applejack raised an eyebrow. “Oh, hogwash. There ain’t such a thing as being bad luck. Sure, sometimes bad things happen, but--”

The fella shook his head. “No, I’m serious. I’m cursed. Everywhere I go, bad things happen.”

At the mention of a ‘curse,’ Applejack flinched and snorted. “Cursed? Now that ain’t true.”

“Oh, but it is. A witch put this curse on me.” He pointed up at the storm cloud above him. “Ever since, this cloud has been haunting me. It is a sign. A warning to all of my bad luck. I’m just no good.”

The little guy reached for the apples and bid his farewells, but Applejack wouldn't let him go. “Oh no you don’t. You ain't leaving until you tell me your name.”

“Woebegone. My name is Woebegone.”

“Well, Woebegone--” Applejack raised her head and put on a huge smile. “--I don’t believe in such things as curses.”

“Whether you believe in them or not doesn’t change my luck. Thank you for the food, Applejack.” Woebegone dipped his head in a courteous nod and took a bite into an apple as he turned away. Applejack wouldn’t let him leave just like that. She’d tried to think of something to say--this Woebegone fella was so accepting of his defeated state that it irritated her. How could he be so willing to accept his suffering? Did he not have a sense of pride or self-respect?

Before she could call him back, Woebegone grabbed his throat and coughed violently before spitting up on the ground. The distressing noises hammered her nerves, and she rushed up to Woebegone and started beating him on the back.

“No, no. I’m not choking,” said Woebegone between coughs. He pointed to the glob of chewed apple on the ground. Applejack looked at it and flinched in disgust, and her heart sank because of her horrible mistake.

In the apple mush were a bunch of crawling, wriggling worms. She looked over Woebegone’s shoulder at the apple in his hand, and there were even more of the disgusting varmints.

“Oh, shucks, I’m awfully sorry about that.” She ran back to the stall and grabbed a new apple. “Here you go, sugarcube.”

Woebegone shook his head and dropped the wormy apple before taking the new apple from Applejack. “No, no. It’s not your fault. It was just my curse.” He took a bite of the new apple.

Applejack resisted the urge to roll her eyes. “It’s probably just a coincidence. You don’t have bad--”

A piece of unchewed apple fell out of Woebegones mouth and he shuddered. Applejack moved in closer to get a look at what was wrong. The sight made her gag. The entire inside of the apple was a mushy brown, as if it had rotted from the inside out.

But how!? It was so firm and a healthy red!

She snatched the rotten apple from Woebegone’s hand and threw it over her shoulder. “Like I said. Coincidences. You’re just focusing on the bad stuff. I’ll eat my hat if that other apple I gave you isn’t fresh and worm-free.”

Woebegone dismissively shrugged and took a bite of the apple. He looked down at the apple as he chewed and swallowed. “Blegh.”

Applejack chewed on her tongue to control herself. “What’s wrong with that one?” She took the apple and looked at the exposed apple flesh. “Well, pull my tail and slap me silly.”

Under the apple skin was a fresh and worm-free orange.

“I don’t like oranges,” commented Woebegone. “I’m terribly sorry, I’ll--”

“No!” interrupted Applejack. “You’re not going to leave my stall without some delicious apples!” She rushed behind Woebegone and pushed him back to her stall. Once he was in place, she rushed back behind the stall and grabbed several apples before pulling out a knife. She ignored Woebegone’s sudden step back at the flash of the blade as she chopped up several apples. With the job done without incident, she put the knife down beside her at the far side of the stall before inspecting each apple slice. A quick nibble on one piece proved the apples were great as usual and put the slices into a paper bag and hoofed it over to Woebegone, who never took his eyes off the knife. “There ya go! Fresh apples. No charge.”

Woebegone looked down at the paper bag and hugged it close to him to keep it out of the rain. He took out a piece, inspected it, and ate it, then hummed in delight and smiled as he crunched on the slice. “Thank you so much, Applejack.” He waved and turned around. “Well, I must be going. Have a nice day.”

Applejack waved back. What he needs is more than a pick-me-up. Proof that his bad luck isn’t a curse. If only…! I know! She trotted over to Woebegone. “Now hold on there, partner.”

Slowly, Woebegone turned to Applejack. “I’m sorry, did I do something?”

“You didn’t, sugarcube.” Applejack shook her head. “Listen, I’m still not convinced, but if you really think you have a curse, I know just the pony who can help you.”

Those little eyes of Woebegone opened wide from their usual half-lidded gaze. “Are you sure? Several have tried to help me before… and…”

“Phooey! Come on, I’ll take you to her. Let me just close my stall and--”

A loud crack interrupted her, and she whipped around just in time to see the sign fall from one of the supporting beams. The corner slammed into the stall below and knocked the center board loose, catapulting the knife away from the cart and down the street. It whizzed through the air and in-between a pony’s ears and sliced through a bag another pony was holding before lodging itself into the side of a building. The first pony, Rarity, wailed as she tried to recover her curly purple mane from the ground, and the second one, Derpy, mourned the muffins that poured out of her bag and into the mud.

A shiver went down Applejack’s spine. “Tell you what. I need to do some cleaning up. I’ll meet you at Sugarcube Corner in a few, then I can take you to see my friend. Okay?”

“Where’s that?”

“Just turn a left at that corner, then a right. It looks like a gingerbread house, can’t miss it.”

Applejack watched as Woebegone trudged around the corner, and as he passed Lyra, a chord on her lyre snapped and whipped her in the eye. She said words that made the foals cry.

Twilight is gonna be busier than a one-armed monkey with two bananas with that one. She turned around to clean up her stall and apologize to Rarity and Derpy, but before she could do any of those, she noticed a large commotion coming from the septic pipe from earlier.

Many more streams of water were spraying in all directions with an unsettling amount of force, and ponies backed off in a panic as one pony holding a wrench climbed out of the hole and screamed, “The pressure’s too much! Everypony back, she’s gonna blow!”

There was a loud boom, and the whole street was painted brown.


Twilight’s ears twitched when she heard the boom echoing from town. She looked up from the book she was reading just outside the lopsided castle. “What the hay was that!?”

Spike scratched his head. “I dunno. Sounded like an explosion of some sort. Doesn’t seem like a monster attack, though.”

Starlight jumped up alert. “Is Ponyville under attack?”

“Nah,” Spike said with a wave of his hand. “Stuff like that happens here all the time. If we were to check out every explosion, scream, or some other disturbance, we’d get nothing done.”

“Still, I don’t think that was a good noise.”

“You’re right.” Twilight closed her book. “Once we’re finished here, let’s go check it out. It’s not like we’re going to be using the castle for a while.”

They wouldn’t have to wait long before investigating because the carpenter they hired walked back from underneath the castle. “Well, Princess Twilight. I have gone over the damages.”


“The castle’s foundation is fixable. But since we’re talking about a solid crystal castle on top of soft earth, it won’t be cheap to fix.”

Twilight bit her tongue. “How much are we talking about?”

The carpenter handed her a rolled-up piece of paper. Twilight unfurled it, glanced over it, and sighed. “Oh, that’s not too much. I was expecting a lot more.” She took another look at the numbers before her. “Why do you have three zeros after the decimal? Are you that precise with your estimates?”

The inspector walked up next to Twilight. “That? That’s a comma.”

“Ffffffudge muffins.”

Author's Note:

Woebegone is a Gen 1 character that almost gets pony babies killed and causes a wildfire that destroyed a whole forest. How did someone so brutal not get a story on this site until now? And Troubleshoes doesn't count!