NOTE: I thought of this story when I heard the demo of "Oogie Boogie's Song" that Danny Elfman sang. It sounded like an evil younger Jack, so I decided it would be a good story.
Jack: Another Side
Chapter 1: Halloweentown Trouble
It was a dark day in Halloweentown…This of course was usual. Halloween had just ended and everyone was celebrating. Only the citizens didn't know that it would be their darkest time ever, and not in the good way. But nothing hinted it yet…
The Mayor as he did every year was handing out awards for outstanding achievement during the night. Of course Tim Skellington had won first prize. He was the Pumpkin King of Halloweentown. His teenage son, Jack, was very proud of his father, but didn't feel the same as him about Halloween. He wanted to do more than just scare. Of course he knew he couldn't do anything of the sort, it would mean exile. Halloween isn't for evil things. But Jack wanted it to be, he felt like something was missing from his life. An empty place inside of him. He was going to be crowned the Pumpkin King in just a few Halloweens, but he wasn't ready yet. He just didn't feel right about it.
Even though Jack wasn't really in a Halloween-ish mood, he still went and celebrated. He felt a little like staying away from his father though, because every time he came near him during Halloween, it was always the talk about responsibility about being the Pumpkin King soon, and that it was going to be so great. Jack never had the heart to tell him that he didn't want to be the Pumpkin King. But of course as he walked around greeting everyone in the town, he ran into the Mayor. This was also one of the people Jack hated running into.
"Why if it isn't the soon-to-be Pumpkin King!" He said as he embraced Jack in a hug that was much too tight. "How horrible has your Halloween been tonight, Jack?" he asked jollily.
"Oh, just horrific!" Jack exclaimed half-heartedly. He wasn't really in the mood to talk to a Mayor who has a meltdown if you said the littlest thing to hurt his feelings.
"I know this is a little early, but I have some special plans set aside for Halloween when you're King. Want to go over some with me?" He asked as if Jack had no choice.
"You know sir, I would love to, but I really have to go see my father right now to…to congratulate him on this year's Halloween!" Jack quickly said without thinking to get out of the conversation.
"Alright Jack, but sometime I want to read these over with you!" He said pulling out some blueprints for upcoming Halloweens.
"I'll try to find some time sir!" Jack called as he ran off towards where his father was. Of course he didn't really want to, but if he didn't go, the Mayor would get suspicious. You see, the Mayor talks with Tim about EVERYTHING, and it would eventually come up in conversation. So Jack walked through the crowds of monsters and ghouls. Coincidentally, he ran into Sally, the rag doll.
"Oh, hello Jack! How's your Halloween?" She asked him.
"Oh, it's just great Sally!" He said as he tried to walk away from her.
"Jack, is there something wrong? You look sad," she said to him with a puzzled look on her face.
"No, no. Everything is just fine! Now if you'll excuse me, I have to go see my father.
"Oh, of course Jack," she said and waved to him as he scurried off. "There is something bothering Jack, what could it be?" She asked when suddenly she was grabbed.
"Sally, what did I say about running off? I told you to stay at the lab and you disobeyed me! You are getting a punishment for this young lady!" Dr. Finkelstein as he pulled Sally away from the crowd.
"Oh please, you never let me do anything! I want to go out into the world!"
"Ideas like that will get you into places you don't belong, now COME ON!" So as Sally was dragged away, Jack was off to find his father, who not surprising was crowded by all the creatures of town.
"Dad, can I talk to you alone?" he asked as the other monsters welcomed him to the conversation.
"Why, of course son! Guys, if you don't mind, a little privacy." So now the town square was just Tim and Jack.
"Father, I came to congratulate you on this year's Halloween! It sure has been great!"
"Why thank you Jack! You know, in a few years it will be you with all this fame. Are you excited?" He asked excitedly.
"You bet I am Dad! I can't wait until I'm the Pumpkin King!" Jack lied to sound nice.
"Well that's great! I've heard that the Mayor wants to talk to you about the next Halloween plans! Why don't we both go tomorrow? It will be great!" He asked Jack.
"That sounds just fine Dad, but if you'll excuse me, I think I've been Halloween overloaded. I'm going to go back to the house."
"Sure thing Jack. You're probably too excited to stay out any longer! I'll see you in the morning!" He waved to Jack as he walked back toward the Skellington house. And that night, Jack had no sleep at all, worrying about the next day…