Episode 17: Rarity on the Daily Show

Like always, whenever Jon got sent to Equestria he usually did so in an instant, to the point where on more than one occasion he would miss the transition completely because he blinked. In this case Jon was so lost in his thoughts that he barely noticed that he was now staring at a wall. That was not the only thing he noticed; when Jon took a step back he bumped his leg on something hard and low to the ground. When he turned around to see what it was, fearing that it might’ve been a wayward pony, he soon realized that he was a foot away from huge gaping hole in the earth otherwise known as a water well.

“Jesus, Twilight.” Jon pressed himself against the wall he moments ago staring at. “Cutting it pretty close aren’t ya.”

Like before Twilight’s powers weren’t as focused as her mentor so when she sent Jon to Ponyville she did so aimlessly within a certain radius. It wasn’t as dangerous as Trixie teleporting Jon to Cloudsdale, but the random factor meant there were odd, often dangerous, results like this.

However, dangerous opportunities aside, Twilight did get her spell right in that Jon was now on the Eastern end of Ponyville.

“Alright,” Jon thought as he began to walk down an adjacent, and empty dirt road. “Time to catch a ride.”

What most people, incorrectly, assume about Jon Stewart is that he was born and raised in New York; but this was only half the story. He was born in New York yes but his family then moved to New Jersey; it was only later in his life did he move back to his beloved city and start his life as an entertainer. And it was during this jovial return did he discover a proficient, and completely necessary, talent at memorizing street layouts.

If you are ever lost in New York and need to go somewhere, Jon could give you directions better than any talking GPS and tell you the best restaurant along the way. This talent also extended to Equestria as well.

Jon was proud in his knowledge of the Ponyville layout; especially since he’d only been here a few times. He knew roughly what attractions and where some ponies lived.

If you want a good slice of cake you go to Sugar Cube corner on Apple avenue on the west side. If you want to buy a souvenir or wish to sell goods to some traders you go to market street. If you want to talk to the mayor or apply for a permit you head to the financial district in the very center of town. And of course if you want to ride a hot air balloon or take the train out of town to say somewhere like, Canterlot Castle... you head towards the west side of Ponyville, otherwise known as the industrial part of town.

As Jon made his way down his current street he knew that he was a few blocks away from hitching a ride on any number of public transportation. From there he would go to Canterlot and catch a lift on one of the trolleys straight up to the Castle.

And, although he hated having to rely on this, his plan, for if he caught some slack for trying to go to the castle, would be to flaunt his celebrity status and remind those that he and the Princess were business partners. The plan was solid in Jon’s head; right now he just needed a ride.

Because of the human world and Equestria existing in completely different universes on two completely different solar systems, their respective calendars were nowhere near in synch. Sometimes when Jon arrived in Equestria it would be night while back home it was morning, on some occasions their time zones would be relatively the same (bar a few hours or so) but in this case while it was almost time for Jon to go to bed, here in Equestria most ponies were still sleeping because it was very early in the morning.

A cold wind blew through the empty streets of Ponyville forcing Jon to button up his sports jacket all the way up. It was still too early for most ponies to be up and about, and for Jon that was most preferable, it meant that he didn’t have to waste any time talking to would be fans. At least that’s what he thought; that cold wind could very well have been a warning for what was flying right behind just a few inches away.

“What’cha doing?” A voice chimed.

“GAH!” Jon yelped as he jumped forward and spun around with his hand over his heart. It took a second to identify the Pegasus hovering in front of him.

The first thing he noticed, which was this pony's most apparent feature, wasn’t the blonde hair, grey body, or awkward flying... it was her eyes.

“D-Derpy?” Jon asked. Hearing her name caused the carefree Pegasus to squint her eyes and give a judgmental stare.

“How do you know my name?” She asked, as she flew higher over Jon’s head almost to the point where she was hovering upside down. “Have we met?”

Jon couldn't tell if she was joking or not; then he realized who he was talking to.

“Y-you’re kidding right? Derpy... i-it’s me, Jon... Jon Stewart?” He said which only seemed to make her more confused. “I had you on my show?”

“Ummmm.... wha?” She said, scrunching nose in confusion.

“Oh come on, seriously!” Jon blurted. “You were the first pony I ever had on my show! You brought your book and everything! Don’t you remember.”

In response to his claims Derpy flew in uncomfortably close to Jon’s face. With eyes in all directions and nose still krinkled she examined Jon’s face and even starting to smell him to see if anything would spark.

“Well?” Jon said. Finally she spoke. “You remember me?”

“Nope.” She chuckled, as she rubbed the back of her head and stuck her tongue out innocently.

“Seriously!” He bellowed. “You told me it was the best night of your life! And you don’t even recognize me!”

Again Derpy flew in close, this time pressing her face against Jon’s, like a child making funny faces on a surface of a window to get a better look. He would have sighed in discomfort but his entire face was smothered. In time however Derpy recoiled back and gasped so loud Jon thought she might wake up the entire town.

“Holy crackers!” She yelled, her eyes now sparkling. “You.... you...”

“Yeeeeeees.” Jon said leaning forward in anticipation.

“You’re Stephen Colbert!” She announced. A silence once again found it’s place in the empty streets of Ponyville as a devastated Jon Stewart turned on his heels and continued on his way without so much as a word.

As he turned a corner Derpy followed close just overhead.

“Why are you here in Ponyville?” She asked, flying so close that Jon could feel the wind coming off of her wings.

“Well it’s not like you’d even remember but if you must know I’m on my way to Canterlot Castle.” He answered. “I got some... work to do there.”

“I got work too!” She cheerfully announced. “I’m on my way to the post office... I get to deliver all the mail... even the big ones now!”

Stopping for a moment Jon looked behind him then back at Derpy.

“Isn’t the post office over there?” He pointed to the opposite end of where he was heading.

“Yep!” Derpy acknowledged as she continued to follow Jon down the street.

“Aren’t.... aren’t you going to be late?” He asked.

“Late for what?” Derpy asked back.

“L-late for work!” He said in a loud tone so she could hear her.

“Oh... wait where do I work again?” She said causing Jon to slam his palm against his forehead.

“OKAY! How bout this!” Jon yelled as he reached into his coat pocket and took out a piece of paper. It was a report card he received from one of his kids the other day, that he had left in his coat pocket but never got around to actually looking over. “Derpy, take this!”

“Okay!” She trilled, grabbing the note with her mouth. “Now what!”

“Listen carefully Derpy... I want you to deliver this letter for me.” He explained. “I want you to deliver this note for me as fast as you can... first class mail... Can. You. Do. That?”

“Why sure I can!” She boasted as she tried to salute with her hoof only to accidentally wack herself on the nose. “Who do I deliver it to?”

“Listen very, very carefully Derpy.” Jon said, causing her to lift her ear in the wrong direction. “I want you... to deliver this letter to someone called Jon Stewart... I repeat... deliver this letter to Jon Stewart... can you do that, Pony Express?”

“I will do my best!” She assured him and she turned around and flew to where she thought was up in the sky but in fact was towards the ground due to her being upside down. With her flank in the air and her wings dragging her head across the floor she slowly crept along the dirt road while Jon just stood, shaking his head.

“And yet she she’s still better than FedEx.” Jon chuckled as she soon vanished around the corner. As she disappeared something caught his attention from the same area. Another figure emerged going the opposite way of where Derpy was heading; it was a pair of ponies who were as bewildered by Derpy’s actions as one might expect.

Jon’s first instinct was to turn around, walk away and pay no heed to these newcomers, but unfortunately he knew these two, which caused him to freeze in place, unable to move. The two ponies walking caught a glimpse of Jon which shook him down to his very core.

The scene of two parties facing each other on opposite sides of a dirt road looked like something out of an old Clint Eastwood film, only instead of a heroic cowboy who doesn’t follow the rules there was a petrified Jew starting at two little ponies.

One of the ponies Jon only vaguely remembered. She was an Earthpony, her coat was cream colored and mane streaks of dark blue and pink. But the other one Jon knew all too well... he recognized her sea-foam green coat and cyan mane.

“Oh no,” Jon groaned in fear. “Not Lyra.”

Jon had nothing against the lively Unicorn, it’s just that whenever she was around Jon seemed to get hurt. It all started when they first met a few months back and he almost choked to death after being full on tackled by her, and that was just her greeting. Jon’s fear of her only got worse when Queen Chrysalis invaded his show disguised as Lyra, and while Jon knew it wasn’t actually her he couldn't help but equate Lyra with pain when he was being thrown around and suffocated.

That same cold wind once again flew through Jon’s hair, reminding him he needed to be somewhere. Carefully he took a step back, then another hoping that maybe he could get out of here in once piece; no such luck.

“HEY IT’S JON!” Lyra yelled as she bolted in his direction against the wishes of her companion. Change of plans; Jon’s new mission in life was to be anywhere other than where Lyra was.

“FUCK NOT AGAIN!” Jon yelled as he ran down the nearest alleyway as fast as he could without regard for anything in his path.

Despite his age and lack of fitness Jon could run somewhat faster than most ponies (though not for very long) because of his longer legs. Though long legs or not Lyra was fueled with such desires to meet him that she was quickly closing the gap.

All of Jon’s knowledge of the town’s layouts was being put to good use as he ran from street to street in random order to avoid his enclosing heat seeking missile that was Lyra Heartstrings. A few twists and turns later Jon now found himself more towards the center of town, making him an open target.

“Shit!” He thought. “I need to hide!”

The sound of galloping coming from nearby ally made a very nervous Jon Stewart lunge for the first door that he could persuade to open for him. Jumping into whatever establishment he just intruded on he quickly shut the door as quietly as he could and ducked down into a fetal position against its frame. Jon had no idea where he just barged his way into and he didn't care. He could hear the sound of hooves pounding against the ground almost as quickly as his heart was beating and didn't move till the sound of hooves on cobblestone dissipated.

Slowly standing he peered through the window of the door to see a confused Lyra looking all around her before desperately choosing a street to continue her hunt. Jon slumped back down to a sitting position just in time to miss Bon-Bon chasing after her.

“Thank god.” He sighed, trying to catch his breath. After a moment of quiet meditation he opened his eyes to take stock of where he was; and what he saw surprised him.