“Now just what do you think you’re doing?”

King Sombra jerked upward, momentarily startled. He’d been so immersed in his current task he’d not even realized the stern looking mare standing less than six feet from him, holding a clipboard atop a hoof for some reason.

He tilted his curved horn towards the immense power drill he was holding. “What does it look like? I’m drilling my way back inside the Empire.”

“I see.” The mare raised her clipboard and made a quick note with a quill. “And you do realize the Crystal Empire walls are close to twenty feet thick on all sides?”

“I… do,” Sombra replied awkwardly, sheepishly glancing at his progress—twelve inches inside the wall at best. He’d been working on it all morning, too. “But when there’s a will, there’s a way! And all that hippy-happy crap ponies say to make them feel better when they just plain suck.”

“By this rate, it’ll take you years to get in.”

“Uh-huh.”

“Is there a backup plan in place?”

“Nope.”

“I see.” She made another mark, grimacing sourly.

Sombra took notice, grimacing sourly himself. Only better. “Something I can help you with, Mrs…?”

“Harshwhinny,” the mare finished coldly. “And, no, I am strictly here to supervise and review. I…” She chewed on her tongue for a moment. “I… reviewed my room a little too harshly this morning, and now I believe it best if I hide outside the Empire walls for a while. So, tell me, what attempt number is this now?”

Sombra shrugged, setting down his overly large drill with a soft thud. “I don’t know. You think I keep track of this stuff? Second attempt, maybe? Forty-fifth? Eight-hundred and eight?”

Mrs. Harshwhinny wrote on her clipboard again, muttering to herself, “Clear lack of planning or scheduling; rudimentary equipment and materials; unimaginative break-in procedures; offensive body odour—”

“Hey!” Sombra barked. “You try living in the woods and smelling like a rose every day!”

Mrs. Harshwhinny raised a thin brow. “Are you not the current owner of an amusement park, a movie theatre, and a bar?”

“Doesn’t mean that I sleep in any of them!” Sombra answered sharply. “Or… installed showers in any of them. But that’s besides the point!” He glanced upward towards the Empire—a faint smirk on his lips. “If I’m going to sleep anywhere, it’s got to be in there! Where I belong! And that’s that.”

“That sure is that,” Mrs. Harshwhinny said, scribbling some more. She soon flipped to a fresh blank page. “And if this ‘drilling’ scheme takes years to pull off, just how does one make sure no guards accidentally happen upon it in mid-progress?”

“You think this is my first tunnel job? Please.” With that said, Sombra retrieved a rectangular poster from his shabby backpack and quickly slapped it over the small hole using wads of chewed up gum to hold it in place. “You like?”

The poster was of Sombra, spread out on a blanket in front of a fire with a single rose clenched between his sharp fangs.

Mrs. Harshwhinny stopped writing, lifting her chin up an inch. “I’m both tempted to give you marks for your boldness… yet take marks away for your cockiness. So, I’ll tell you what: remove that poster from my sight right this instant and I shall reward you one perfect point.”

“Out of?”

“One thousand.”

“Poster stays,” Sombra said with a laugh. “And as if the opinions of others matter to me in the slightest.” He then sneakily angled his head to get a better look at what was written on Harshwhinny’s clipboard.

Rolling her eyes, Mrs. Harshwhinny asked, “Let’s try something simpler, then: origin of evil. Go.”

Sombra winced. “What?”

“What made you the pony you are today?”

“Oh. Well, truth be told, my father was the King before me, and helped indulge my every fantasy. Food. Wealth. Mares. Silver spoons. I had it all. Corrupting me for life, it would seem.”

Finally, Mrs. Harshwhinny smiled. However faint. “Uh-huh. I see. Very good. Would you say your father—”

Sombra suddenly burst out laughing. “Nah, I only said that in jest. When I was younger, I got so lazy I just couldn’t get up anymore. So, I found a slave to do everything for me instead. Then that slave got a slave. And that slave got a slave. And one pyramid scheme later, here we are!”

Mrs. Harshwinny’s small smile disappeared into some unseen blackhole on her face, replaced by a scowl deeper than the pits of Tartarus. “I’ll have you know the only reason I even entered the reviewing world was because my mother was overly harsh on me as a filly. Every day, she’d tell me I wasn’t good enough. Nothing that I did was ‘up to code’. And now I use that same raw anguish to judge others just as she did. I know I may seem harsh to a lot of ponies most of the time, but that’s only because that’s all I’ve ever known.”

Sombra’s pointy ears dropped to his head. “I… I apologize. I didn’t mean to—”

“Now that’s how you monologue an origin story, Mr. Bra. In all honesty, it was I that reviewed my mother’s parenting so harshly she gave me up for adoption at age three. Following that, I reviewed my orphanage until it went out of business two months later. I must say, I’m rather good at what I do.”

Sombra took an instinctive step away from her. “I can see that. So… are we done here? You write enough on that clipboard of yours? I sort of need to get back to the whole ‘re-entering’ my Empire thing.”

“Yes, I do think I’ve seen enough. Here you are. I would say stick it on the fridge, but… I’m reminded you don’t have one.”

She then handed over the few pages she’d been writing on.

Sombra read them over hurriedly. “Three frowny faces. What does that mean?”

“My lowest possible score.”

“But that’s impossible!” Sombra exclaimed. “I’m me, damnit! Have you even reviewed a proper villain before?”

Mrs. Harshwhinny nodded. “Yes, many times, in fact. Queen Chrysalis, Tirek, Discord, Starlight Glimmer, a broken pinball machine—they all scored much higher than you, I’m afraid.”

Sombra sniffled. Then full blown cried. “But t-that’s… unfair!”

“Are you crying? Real tears? I thought you said the simple opinions of others didn’t matter the slightest to you?”

“These aren’t tears! I’m just letting out pure liquid evil, you jerk!”

In a snap, Mrs. Harshwhinny snatched her papers up again, adding colorful tears to all three frowny faces. She handed it back, stabbing it through the tip of Sombra’s horn. She then grinned, admiring her work—a fully broken adult pony coated in tears.

“Moments like these are what make me feel alive,” she said, more to herself than anyone.

Running away from the evilest pony he’d ever encountered up until that point, Sombra yelled back, “You’re going on my list, whoever you are!”

Mrs. Harshwhinny replied happily, “I’m on everyone’s list, sweetie!”

Then she went on to review the snow underhoof for being much too cold.

Sombra glanced down from the tall wooden bucket he sat on, eyes wide and clearly terrified.

“You sure this will work?” he asked the brothers. “Doesn’t look all that safe.”

“Safe?” questioned Flim, in that trademark singsong voice of his. “Why, safe’s my middle name! Ask anyone. Like my brother, Flam! The one’s that standing right next to me! Isn’t that right, Flam!”

Flam, indeed standing right next to him, nodded aggressively. “Sure is! Flim Safe Flam!”

Sombra pointed down at Flam. “So, what’s your middle name, then?”

“Unsafe!” Flam answered, about to pull the lever on the large wooden machine.

“Wait!” Sombra yelled. “What did you call this thing again?”

“A catapult, my dear richy-rich King!” Flim said, waving a foreleg at the contraption. “It takes an object and hurls it far, far away! Or, in this case, directly back inside your precious Crystal Empire. Ready to depart? Is your tray table in its upright and locked position? Did you want a complimentary packet of salted nuts for your flight? Only two bits per compliment.”

“How do I land, though?”

“Got your parachute packed, right?” Flam asked.

Chuckling uneasily, Sombra glanced at the pack on his back. “Oh. Yes. Of course.” He shifted his rump a small bit, causing the mammoth catapult to quiver. “Just how did you get a catapult all the way out here? I thought Twilight Sparkle and her friends were keeping watch over everyone?”

“Why we improvised, of course!” Flim told him happily. He knocked on the side of the catapult, causing it to shake. “See all this wood? Wasn’t there this morning!”

“Sure wasn’t!” his brother agreed.

“Then where did you get it all?” Sombra questioned.

“Rocking chairs!”

“Rocking chairs?” Sombra asked.

“You know how many retirees live here in the Empire? A lot! And you know what their number one pastime is?”

“Rocking in chairs?”

“Not anymore!” Flam declared. “Why should us working ponies be the only ones standing around anymore? Unfair, I say! Unfair to the max! Give me a ‘here here’, brother o’ mine!”

“Here here!” said that particular brother o’ his.

Flam stood next to the catapult lever. “And you know what else they say about rocking chairs, King deep pockets?”

Sombra tapped on his chin. “What?”

“They rock!” Flam said, pulling the lever and sending Sombra soaring…

…directly into the hardpacked ground roughly twelve feet in front of them.

A soft poof! told them both his parachute deployed correctly, somewhere underneath several feet of destroyed wood and metal.

“Hmm,” Flam said, straightening his moustache. “You know what, Flim?”

“What, Flam?”

“Maybe we should’ve unhooked that seatbelt of his first.”

He thought on that. “Maybe we shouldn’t have installed that seatbelt in the first place, Flam.”

“Comedy of errors, this one. Better luck next time. Got that shovel handy, best brother forever?”

“Sure do. Does that mean it’s time to hide another body?”

“Took the words right out of my mouth!”

Each taking a deep breath, they pressed their backs together to sing:

“Looks like it’s tiiiiiime to hiiiiide another boooodddy!

“Six feet deeeeep… with no marker should be good!

“Somewhere deeeeep in the wooooods! To protect all our goooods!

“Oh, yes it’s tiiiime to hide another booooodddy!”

Sombra suddenly groaned somewhere beneath the wreckage, causing both brothers to jolt.

“I thought he was dead!” Flim exclaimed.

Flam’s jaw dropped. “Worse. Alive! Which means he might sue us!”

“Then let us depart this confusing place, brother o’ mine!”

“Posthaste!” his brother agreed. And, so, they did.

And only once Sombra had successfully escaped the wreckage, did he add two more names to his ever-growing list of ponies to destroy:

Numbers 405-406: the nefarious Slim and Jim.

He may or may not have been suffering from a severe head injury at the time.

Atop the Crystal Empire wall, Applejack watched Sombra march back and forth carrying his trademark protest sign. “MAKE THE EMPIRE GREAT AGAIN!”, it read. Applejack sighed, lowering her head to rest on the chilly railing. She brightened once Fluttershy joined her, carrying a tray of hot apple ciders and cinnamon twists.

“Thanks, Fluttershy,” Applejack said with her newfound warm beverage. “Gets mighty boring watching the same fool do the same fool tactics day in a day out. Wish he’d change it up a bit, you know?”

“Oh, I don’t know,” Fluttershy said, blowing on her own steaming drink. “I sorta like the boring, quiet stuff. It’s so peaceful up here, out in the middle of nowhere with nature. And I have to give Sombra credit. He’s been doing this for quite a while now. What’s the longest a villain’s ever attacked us before?”

Applejack cocked a brow. “A day, I reckon. A weekend, tops. Still, some change would be—”

Fluttershy glanced down below with a gasp. “He’s stopped! I think he’s writing something new on his sign.”

Both mares held their breath as they watched Sombra erase his old message and start anew. What he wrote made Applejack laugh while Fluttershy held a hoof to her mouth.

“HUNGER STRIKE!” the latest sign read. “UNTIL JUSTICE IS ACHIEVED!”

Applejack let out a mouthful of cider as she laughed. She shouted to him, “You serious, Sombra? I don’t think I’ve seen you go a whole two hours without eating something!”

Down on the cold ground, Sombra narrowed his eyes as he searched for the source of the voice. “Damn. It’s that apple pony again,” he muttered grumpily.

Applejack only chuckled again. “Thinking about apples already, are you, sugar cube? I reckon you make it half-a-day before you’re begging for table scraps!”

Sombra, meanwhile, appeared on the verge of throwing up. “Is that your real voice, apple pony? Or are you just doing a character? I’m more apt to believe it’s the latter. Is this part of some stand-up routine you perform on weekends, perchance?”

Applejack rolled her eyes. “That theory’s crazier than a racoon covered in powdered sugar trapped in a donut factory.”

Sombra nodded thoughtfully at her. “So, it is true. Can I have tickets to your show, then? Do you have a bit where you say, ‘You know you’re an apple pony when?’”

Applejack furrowed her brow. “I have no idea what you’re getting at, Sombra.”

“You know you’re an apple pony when your momma ripped her dress coon hunting!” Sombra shot back, joyously. “Say, that was a good one!”

“Stop in now!” Applejack warned. “Stop it right now!”

“One more! Just one more! You know you’re an apple pony when you go to the family reunion to score dates!”

Angered, Applejack grabbed the plate of cinnamon twists off the railing and threw them down at Sombra—china plate and all. Sombra sidestepped the projectile easily and grabbed a single cinnamon twist out of the snow, popping it in his mouth.

“Now who’s the idiot!” Applejack shouted. “Hunger strike’s over! One whole minute! Congrats!”

Sombra only smirked at her as he chewed. “What are you talking about? I’m just on a break right now. I’ll get back to the strike right after this.”

“Hunger strikes don’t get breaks, Sombra. If you start a strike, you gotta stop eating for good.”

Down below, Sombra gulped dryly, eyes bulging.

“Hunger strikes don’t take breaks? Not even for snacks?”

Applejack shook her head. “Nope.”

“Then screeeeeeeeeeeewwwwwwww that!” Sombra said, trotting away in the direction of his bar. And three servings of some deep-fried mozzarella sticks.

Author's Notes:

So this is about half of some short (very short) Sombra/pony interactions I want to get to. Others including Luna, Celestia, Chrysalis and a few more.

Oh. And Flurry Heart. Always Flurry Heart.