The Nightmare Before Ponyville

by Grim The Pony Reaper

Rating: everyone
Tags: Adventure, Princess Celestia, Crossover, Main 6, Princess Luna, My Little Pony: Friendship is Magic, Cutie Mark Crusaders, Other
Length: 2832

Just a few Halloweens after that... incident....Jack Skellington opens another one of the doors, but what he finds isn't just a holiday...

Just a few Halloweens after that... incident....Jack Skellington opens another one of the doors, but what he finds isn't just a holiday...
Watch Jack stumble through adventures in the most unlikely place possible!

My first crossover.... Constructive criticism is welcomed. Anything for me to become a better writer.
I hope you enjoy!!

Published 2015-05-17 04:30:02 UTC
Last updated 2015-05-17 04:30:02 UTC

Prologue

It was a few years after the events known as The Nightmare Before Christmas, and unfortunately, Jack Skellington was running out of ideas, and began to become bored. Now, we both know what happened the last time the King of the Pumpkin Patch was bored: that certain holiday that everybody knows about. So, soon after a idea popped in Jack's head, Jack went to town square, and called a meeting.

"Citizens of Halloween Town!! I have an announcement to make!!" As the townspeople looked on with interest, Jack announced, "I will be taking a leave for a while, but do not worry, for I shall return, with grander ideas for next Halloween!" The townspeople were both nervous and excited, but the excited part seemed to triumph with most.

Jack once again started journeying through the woods past the graveyard. A few minutes later, without too much of a walk, Jack found The Doors. He put his bony hand to his chin, wondering which door to go through. Then he spotted something in the corner of his eye socket, something that he never saw before. A door hiding behind all the others, neglected.

The door was shaped like a horse, rearing up, but something was...off. This wasn't like a skeleton steed he found in the wilderness. In fact, it seemed like it would be ....

Alive...  Jack thought, just like last time.  He slowly opened the door, taking caution as he did so. He looked up.Nothing. He looked down.Still nothing. But soon after, when his back was turned, he saw something. A leaf. Then he saw two, then three, and then a barrage of them came and swarmed his field of vision. Soon after, a strong wind accompanied the leaves, and pulled the skeleton in.

After what seemed like forever, Jack landed on solid ground. He seemed to be in a forest, but he quickly realized that it was not the same forest he was in just a few minutes ago. The trees back home never had apples on them.  However, when he started to walk, he almost instantly noticed that it wasn't the only change.

He was literally changed into another thing, in the same shape of the door.Well, at least i'm not all changed. It was true, even though he was an animal now, he was still his skeletal, bony self. He even had his old suit! The only problem was he didn't know how to walk like this. An even bigger problem however, he didn't know where to go. His thoughts were distracted, however, when a small voice came buzzing by his skull.

"Well howdy, mister! Nice costume!" Jack turned around, yet saw nothing. Left, right, up, nothing. "Down here!" Just as the voice instructed, Jack looked down and saw a strange creature with a bow on its head, similar to him. Is this what everyone looks like? Once again, the strange newcomer talked. "But, why aren't you at Ponyville celebrating like the others?" To this, Jack's curiosity peaked.

"Ponyville?", Jack responded. When the creature heard this, it slowly pointed with its hoof in a direction Jack forgot to look towards.  When he turned his skull, he could see a village celebrating some sort of occasion.  He walked(for some reason, it felt natural) towards the town, but before he did, he concluded the conversation with the pony. "Ummm... thank you."

When he got there, he noticed a banner near the entrance of the town that read,"Happy Nightmare Night!!" Jack was instantly confused, but when he looked around, he noticed something amazing. There was trick or treaters, monsters, candy, bobbing for apples, scary sights, the works, but the strangest thing is that they were all pony-like! Jack hid behind a stack of hay, and took everything in.

What's this?

What's this? There's ponies everywhere!

What's this? They're flying through the air.

What's this? I can't believe my eyes, I must be dreaming, Wake up, Jack, this isn't fair!

What's this?

Jack started to trot down the street.

What's this? Well, this I can't believe!

What's this? It's just like Halloween!

What's this? How was this all brought? Halloween can't just be taught! Maybe all this is a thought?! What is THIS?!?

What's this?

Jack, almost instantly, jumped up to the rooftops.

This is so very strange, I almost can't believe my eyes.

The one thing that I see is the very one I left behind!

And there are all these ponies! And they're all just singing songs!

I truly feel this happiness I left for so darn long.....

What's this!?!?

Chapter 1

While Jack was singing his song elsewhere, Twilight Sparkle was getting a schedule ready for the night. When she finished, she started to walk out the door, but a certain assistant of hers wanted to ask her something.

"Twilight? Why don't you have a costume on?" The newest alicorn turned to her assistant and responded,

"Unfortunately, since I'm a princess now, I'm in charge of supervising the entire celebration, and that sort of means no dressing up. Speaking of which, though," Twilight looked at Spike with confusion, "where's your costume?" Spike simply replied,

"I have my costume! I'm going as a dragon!" The two stood still in awkward silence for a while, when Twilight finally said,

"You do know you are a dragon, right?" Spike just responded with a chuckle,

"That's why it was so easy for me to get ready!"Another awkward silence filled the room, but soon broke when a pink pony came bursting through the door, catching her breath.

"TWILIGHT!!" Pinkie Pie shouted, still trying to catch her breath. Twilight sighed, knowing if Pinkie was involved, her schedule was probably moot. She turned around to talk to her.

"Yes, Pinkie?" The party pony stopped catching her breath instantly, and yelled,

"Theresthisnewponythatshowedupjustafewminutesagoandhecameincostumeithinkhesherefortheholidaybutimnot..."

"PINKIE, SLOW DOWN!!!" Twilight boomed. Both Spike and Pinkie looked at Twilight with surprise. Twilight started to look a little sheepish, and almost whispered, "Sorry, I'm still getting used to the Royal Canterlot Voice. Sorry. Ummm, please continue." After she said this, Pinkie started bouncing up and down and exclaimed, " There's a new pony here, and I think he's here for the Nightmare Night party!" Twilight seemed a little surprised at this new information.

"Well, this is a little sudden. What do you think he's here for?" Pinkie just kept bouncing on the walls, completely unfazed by Twilight's slight concern.

"I don't know, but what I do know is that I have to find out where he lives so I can throw him a PARTY!!!" As soon as Pinkie said this, she zoomed out the door, but suddenly ran back in. "Oh, and he looks like a skeleton in a suit." And she zoomed off again. Twilight, once again, sighed.

As Jack was admiring the town, he started to see something in the distance. He looked at it with interest, and quickly noticed it was coming closer, and closer.........and closer really fast. It's still going. It's... not slowing down.... Oh no. That was the last thought he had before something almost hitting Mach 2 crashed into him with full force.

The only thought Jack had immediately when he saw his blurry vision was, simply,If I wasn't dead already, I would be now. Literally everything was sore in his bones. Luckily, it wasn't too sore, for some reason. "Hehe, um, excuse me?" As he heard this, he started to focus his sight on the blue blob directly in front of him. After a few seconds of complete disorientation, the pieces started putting themselves together, and Jack's vision came back to reveal... a winged pony.

"Sorry, just lost control for a few seconds. You okay?" Jack just nodded. She extended a hoof out to Jack, which after a few seconds of confusion about the situation, he took and pulled himself up. "Sure you're okay? That was a pretty big crash." The skeleton cracked his spine, and replied,

"Well, if I wasn't dead, I wouldn't be." Rainbow (We all know who she is except Jack) looked at him with confusion, then saw all of him, and got the "joke".

"Heh, funny. Nice costume, by the way." Pointing to Jack. Now, it was the skeleton's turn to be confused.

"What is it these ponies keep saying about a costume?" Rainbow chuckled a bit at the supposed humor, then looked at the dead serious face of Jack. Her smile slowly turned into a frown, and then her jaw hung open a bit.

"Wait, you're... serious?" She stepped up to him, which he backpedaled a bit to in return, but not much. She, with a little hesitation, touched his skull. It feels... real. Then she touched a different part of his skull, only to find the same outcome. Then, she did something that she had to force herself to do.

She reached out to his eye, seeing if he would flinch. Jack didn't too badly. Then she tried to touch the fake black lid that was obviously covering his eye. She didn't find it. She reached further, trying to touch it. Still, she didn't find anything. Then she reached further, and further, and she finally touched something, however, it was not fabric. It was bone. Then Rainbow looked at her hoof, which was, undoubtedly  lodged in Jack's eye socket. She reached back incredibly quickly. "Oh... my.... CELESTIA!!!" And with that, she took off with amazing speeds. To this, Jack just shrugged.

As Pinkie was running towards Jack, eager to formally welcome him to Ponyville,  Rainbow slammed into her. "Wowie, Dash, what's the rush?" As Dash caught her breath, she got out,

"Pony *wheeze* skeleton *gasp* not alive." When Pinkie heard this, she realized she must have been talking about the new pony.

"You mean the new pony dressed as a skeleton in a suit that came here for Nightmare Night is ACTUALLY a skeleton?!?! IN A SUIT?!?!?!" To this, Dash just nodded with fear in her eyes. " That... is... AMAZING!!" Pinkie started sprinting for the new pony, and soon after, Rainbow tackled her.

"No!! Don't go! That pony can't be good!" To this, Pinkie just wiggled out of her grasp and giggled.

"Don't be silly, Dashie! Just because a pony isn't alive doesn't mean they don't have a heart! Oh, wait, it does... I mean feelings! That's what I meant!" To this, RD just facehoofed. But then she thought about what she could do in this situation.

"Fine, you can greet him," Rainbow pounded her hooves together with a sinister look on her face, "but I'm tagging along." At this, Pinkie smiled and nodded, completely unaware of what was going to happen.

Jack still was travelling Ponyville, but something was definitely on his mind.This has been an extremely eventful 4 minutes... "THERE!!", he heard someone scream, and then something caught his eye. He turned to the right on the crossroads he was on, only to find unluckiness. For there he saw two ponies traveling in his direction at incredibly high speeds with no signs of stopping.

........uh oh.

Chapter 2

"I'M COMING FOR YA, YOU UNDEAD FREAK!!!" Rainbow shouted with anger. Pinkie shouted, with joy instead of hate,

"Me TOO!" Jack didn't know what to do. His mind was racing, trying to figure out how to shake these ponies of his metaphorical tail(not his real tail, mind you). What do I do? What do I do? Then he noticed something: The moon. It was a moonlit night, which meant Jack could use his skills.

"He's leaving!" Rainbow picked up speed, trying to catch up to the skeleton pony, who was currently going to an alley. She got to said alley in mere seconds, but when she got there, however, there was nopony to be seen. "What? Where is he?" Pinkie, totally oblivious to Rainbow's worry, exclaimed,

"OO, he's fast!" Most ponies would've given up at this point, but all we all know, Rainbow Dash hates losing. She waved a hoof at Pinkie, trying to get her to move.

"Come on! We gotta keep looking!" Pinkie just OKed her and bounced along. Little did they know, Jack was hiding in the shadows of the alley, waiting patiently for them to leave. A few seconds later of their departure, he sprinted in the other direction.

He kept running, and running, and didn't stop for a good while, until something stopped him for him. More specifically, knocked him on the ground. When he got back up, he saw something to behold. A castle, made entirely out of crystal. Stranger and stranger..., Jack thought as he knocked on the door.

"Door's open!" Twilight announced loud enough for the pony outside her entrance to hear. As she heard the familiar creak of the door, she turned away from her potion making kit to welcome the unexpected guest. "Hello, how can I help..... you...." Twilight finished with uncertainty when a pony she never saw before in town came in. Although she remembered Pinkie saying something about a new pony.... "Oh, and he looks like a skeleton in a suit!" Realizing this pony fit the description, she started to feel a little calmer now that she knew something.

"I'm sorry to intrude, but could you help me? There are two ponies chasing me, and I have no idea WHY!" Twilight thought of various reasons why someone would be chasing a new pony.

"Does somepony have a grudge against you?" Jack thought for a few seconds, putting his bony hoof to his muzzle, and he came up with an answer.

"I wouldn't think so, I just got here today. I'm traveling from from a distant place you see." Twilight thought of a similar case with Zecora.

"Maybe because of your appearance?" Then she realized, It's Nightmare Night! Just because I can't dress up doesn't mean other ponies can't! "No, that couldn't be it.", Twilight said out loud, disproving herself. She tried to come up with another logical reason. "Maybe it's because of the ponies themselves. What did they look like?" As Jack tried to remember, the two mentioned came bursting through the door.

"Like that," Jack answered calmly, pointing to the two Elements of Harmony. Twilight looked at her friends and Jack with confusion. Why would they be chasing...

"YOU!" Twilight's thoughts were interrupted with Rainbow's shout and immediate chase. Luckily for him, Jack's assaulter was stopped by Twilight biting on her tail, using her own wings to try to push both of them back. This was followed by Pinkie giving the pegasus in the room a disapproving look.

"Rainbow Dash! I thought we agreed on no violence!" Pinkie scolded. As an argument brewed between the friends, Jack finally stepped up with a shout.

"WHAT IS GOING ON HERE?!?!" All others looked at him blankly. Jack continued his questioning with a look that just said, "Well?" After a short silence, Pinkie finally spoke up.

"Well, I always try to welcome the ponies that are new to Ponyville. But... why did you tag along Dash?" Everypony looked at her, expecting an answer.

"Well ya see.... I...." Rainbow stuttered out nervously. "Well, I'm not always like.." Twilight rolled her eyes and waved a hoof, motioning for her to go on. Rainbow looked a little nervous still, and then hung her head in shame. "I get violent when I'm scared."  You could hear a facehoof from everypony in the room.

"Again, really sorry, but taking a second look at ya, you look pretty metal." Rainbow's statement made Jack confused.

"Ummm, metal?" Rainbow waved a hoof, trying to calm his uneasiness.

"It's fine, not a lot of ponies here know about it, but some of it is really good! Have you ever heard of Three Days Graze?" To this, Jack just shook his head. "You should hear it." He just shrugged, and walked off. Twilight, however, took his place.

"What I can't understand, Rainbow, is why you were so scared of him. I mean, it's only a costume." Pinkie magically appeared next to them to join in on the conversation.

"That's the thing, Twilight! IT ISN'T!" Pinkie yelled, all the while keeping a smile on her face.Twilight looked at her friends with disbelief.

"You mean, you think he's actually..." Twilight let out with a mix of disbelief, laughter, and condescension. They both nodded their heads, although Pinkie nodded much more rapidly.

"Uh, Huh! Prove it, Jackie!" Pinkie ended with a point to the skeleton pony. Jack looked at them, and then pointed to himself with a confused face. When Pinkie nodded, he responded.

"All right, then." He stood on his hind legs, put his hooves on his skull, and took his head off. All of the ponies in the room dropped their jaws at this sight. He then proceeded to wave, while the head in his hoof smiled. What got everypony's attention, however, was the lavender alicorn unconscious on the rug. Jack put his head back on with a confused look on his face. "Was it something I did?"