Author's Note: Time for Halloween Town to receive its resident rogue. So, how did Oscar Bogart become Oogie Boogie? Only one way to find out. But, once again, I must state that I had no part of The Nightmare Before Christmas. You can all thank Mr. Burton, Mr. Elfman, Disney, Touchstone Pictures for that. Gamers, if you wish, give props to Capcom for the continuation. The plot of this story is mine though, as is one of the stars and narrator, former Pumpkin King Henry Cadaver. He'll take things from here. (Re-edit comment: Coming up with this part was actually pretty fun. Not so much the demise as everything else.)
Now, if any of you are looking for a moral to Oscar's story, it is simply this: never, ever, double-cross people in power. They will find out, and they will get you. Besides, it's not a very honest thing to do. Power is not worth Oscar's fate, as you will see if you can bear to watch. Alas, it is rather tempting to become all-powerful, but it comes with much responsibility. Apparently, no one bothered to tell Oscar that before I officially met him.
— Henry Cadaver
October 31st, 1927
Where the hell was she? Oscar had been waiting in the alley since eight o'clock in the evening. Mr. Bogart impatiently tapped his cane over and over on the ground as he checked his pocket watch. Ten-thirty. Miss Brown had him waiting for two and a half hours. Oscar was beginning to think she ditched him. This didn't go over too well with the Bronzeville Baron.
"Lousy dame, think she can stand me up, me?" Oscar asked himself, catching a glimpse of trick-or-treaters stop by the front of the alley and look at him. "Get lost, you twerps."
Oscar shook his cane at them, scaring the kids away. He chuckled to himself a bit before noticing a feminine figure walk after the kids. Oscar would have ignored, but then he saw that her right leg stuck out from the corner, taunting him, daring him to come over. It was Jane.
"About time, kitten," Oscar said as he walked to the front of the alley and turned to the right.
"Sorry I'm late, Oscar. I've got to look my best for you, and that takes time, sugar," Jane said.
"Got any place in mind for your prize, Miss Brown?"
"The Navy Pier."
"Navy Pier? What's that?"
"Actually, it's the Municipal Pier. They changed the name not too long ago."
"Why the hell do you want to go there?"
"Come on, Oscar, what kind of girl do you think I am? I need to get to know you a little better before we get serious. You said I could spend a night with you, you didn't specify what we'd be doing," Jane said, crossing her arms and smiling victoriously.
"Damn. Alright, we'll go the pier. There better be booze, I'm telling you that right now," Oscar said as he led Jane towards his car.
"It's Chicago, Oscar. What place in this burg wouldn't have booze?"
The drive to the pier was relatively short. Overlooking Lake Michigan, the Navy Pier would have been hard to miss anyway. Although competition from movie houses, clubs, and speakeasies was giving the community center a hard time, it was still a popular place to eat, drink, and be merry. Halloween was in full swing here, although, Jane seemed to go away from the festivities.
"Where are you going?" Oscar asked Jane as she made her way towards the lake. "The party's where the actual food stands are."
"Come on, Oscar. The lake looks great from back here," Jane's voice carried as she walked further and further away. "Look, we can rent a boat."
"Girl, I get seasick," Oscar said as he walked towards her, seeing that she was already walking into a boat.
"Come on. I'll make it worth your while," Jane said flirtatiously.
"Sure, doll. Just don't complain when I throw up on you."
Oscar walked up to Jane before hearing something drop. The platform that connected the boat to the pier had plunged into the lake. The boat was already being steered by someone, someone who wanted to get far away from prying eyes. This is when Oscar realized that he had been tricked.
"You bitch! What are you really planning?" Oscar yelled as he swung at Jane with his snake-handled cane, only to have it wrenched from his hands by a looming figure in a fedora and long coat.
"Right on time, Mr. Capone," Jane said to the figure who now held the cane.
"Capone? As in Al Capone?" Oscar asked, growing slightly pale.
"You know, Oscar, it's not nice to double-cross people who help you," said Mr. Capone.
"He called me a bitch, Al."
"He'll pay for it, Jane. Go downstairs and tell the boys to bring Oscar's going away present.
"Al, buddy, everything's good," Oscar started, nervously watching Jane disappear down the steps that led into the boat's main cabin. "Don't trust that chick, she's a liar."
"Please, Oscar. We're all grown men here. I know what you've been doing behind my back."
"Really?" Oscar asked as he gulped in fear.
"Jane isn't the only pair of eyes I have out on the streets looking at you," Al said as Jane returned from the cabin with Walter, Tom, and Jim, who were all carrying a very large burlap sack.
"You guys were in on this?" Oscar asked the doorman and pair of poker players.
"Why the hell else would we lose to you almost every night?" Tom asked.
"So you want to rule the streets, Oscar? After Bugs and I kill each other off, right?" Al Capone asked in a sinister tone.
"Come on now, Al. It was a joke."
"You must have paid a lot of money to have that joke made into a silver grip for your fat-handling stick," Al pointed out as he looked closely at the cane.
"You can't disrespect me! I'm Oscar Bogart, the Bronzeville Baron!"
"I made you the Bronzeville Baron. You owned Bronzeville because of me."
"Owned?" Oscar asked, feeling sick ad the boat stopped in the middle of the lake.
"Bronzeville is under new management," Al said as he motioned for Tom and Jim to open the burlap sack. "This is what you rule now."
Oscar looked into the bag and almost vomited at what he saw. It was half full of snakes, rats, insects, almost every kind of disgusting creature imaginable. He wondered why it was only half full. Then, he was pushed into the bag by Jane and Walter. He screamed as he was bitten by snakes and rats and clawed at the opened of the sack before it was drawn tightly closed.
"Looks like he didn't mind working for bugs until now," Jim said, making Mr. Capone chuckle.
"Good point, kid."
"Please! Let me out, I can't stand it!" Oscar yelled from the sack.
"You're nothing but a bug to me, Oscar. It's about time I squished you. Throw him over," Al Capone said to Jim, Tom, Walter, and Jane.
The four lifted the squirming bag of vermin and threw it into Lake Michigan. The boat sped back towards the pier as soon as the sack hit the water. As Oscar sank deeper and deeper in the lake, his began to lose consciousness. Some of those snakes must have been poisonous, for he could no longer really see well or hear anything. Soon enough, water filled his lungs as he sank deeper and deeper, until Oscar Bogart breathed no more.
Suddenly, the burlap sack seemed to be going upwards. Oscar's soul didn't notice it, but Henry Cadaver was dragging the burlap sack back to the surface, albeit a completely different surface than Chicago. As he kicked upwards, Henry could make out a small, circular opening. It would be difficult to pull Oscar through, but he had to do it. Henry paddled harder and harder, until his head went above the water, and he looked at his surroundings.
All of Halloween Town had gathered around this well. Henry had dived into it no less than an hour ago and had just returned. Quickly, the Mayor ran over to the well and extended his right arm to Henry. The Pumpkin King got most of himself out just fine. However, he seemed to be holding on to something in the well.
"Henry, dry yourself off first," the Mayor said in a worried tone.
"Don't worry, I can't exactly catch my death of cold," Henry replied as he pulled at what appeared to be a large piece of burlap.
"Ha, good one," the Mayor said, face turning around to she the change in his mood.
"Can I go back in yet?" asked the fish woman who usually resided in the well.
"In a minute," Henry said as he pulled and pulled until the burlap he was pulling at practically flew out of the well and landed on the ground.
It was one of the strangest things Halloween Town had ever seen, and that was a great accomplishment. Henry had brought a massive burlap man from the Real World. He had nubby arms and legs, if one could call them by those names. The top of his head ended in that way as well. As for his mouth, it was a wide open black hole with a snake tongue hanging out of it. When he opened his eyes, he sat straight up and looked around. He was as confused as everyone else, that was for sure.
"Capone? Get your cowardly ass back here!" he yelled as he got up.
"Sir, mind your manners," Henry said to the burlap man as the rest of Halloween Town stood in shock.
"Who the hell are you? You look dead."
"That's because I am dead."
"AHHH!"
"So are you."
"I am not! No one kills, uh... hmmmm... Hey, Dead Boy, do you know who I am?"
"Yes, but it's better if you remember yourself," Henry said. "At least you know who Capone is."
"All I know is that he has a cowardly ass. Help me out here, Dead Boy."
"My name is Henry Cadaver."
"Yeah, yeah. Who cares?" asked the burlap sack man.
"They do. I'm their Pumpkin King," Henry said as he looked towards the Halloween Townsfolk.
"Big whoop. Screw this, I'm out of here."
"Maybe you should let him leave, Henry," the Mayor whispered to the Pumpkin King.
"I can't, Mayor. He's one of us now, no matter how annoying."
"I heard that, Dead Boy. Wanna start something?" asked the thing formerly known as Oscar Bogart as he shook his right arm at Henry, who pulled a loose string on the hem holding it together.
Some insects fell from the newly formed hole as the burlap creature screamed in pain. He drew his arm back to himself and nursed it as if it was broken. He gave Henry a dirty look before backing away from him slowly. Henry Cadaver was no one to mess with, and the new member of Halloween Town learned that the hard way.
"Now that I have your attention, I have to properly welcome you to your new home. This is Halloween Town, where the odd and spooky are celebrated every day of the year. You are our new boogie man."
"Boogie man? What do I do?"
"You scare people, cast your shadow over figures trembling in fear. Though, by your girth, you can probably cast a shadow on the moon."
"And just what the hell is that supposed to mean?"
"Please refrain from cursing, or I'll have to undo your other arm."
"He'll do it too," the Mayor said, beaming at Henry.
"Do I have a name?" the burlap manasked the Pumpkin King, who shook his head.
"It's better if you remember it yourself."
"All I remember besides Capone is Oogie Boogie. Kind of fits, since I'm the boogie man now."
"If it works for you, you can keep it," Henry said.
"Works for me. Now, who wants to sew up my arm?" the newly named Oogie Boogie asked.
A pair of witch sisters volunteered and took Oogie to their house to fix him up. Soon enough, the crowd of townspeople thinned until only Henry and the Mayor were left at the fountain in the center of the square. The Mayor's face switched to a grim mood as he looked into the green water of the fountain. He didn't like Oogie Boogie, not one bit.
"Henry, are you sure he has to stay here?" the Mayor asked.
"I get my orders from higher up, and they specified that he be brought here," Henry said.
"He's not going to replace you one day, is he?"
"Oh, no. It's going to be a while before I find a worthy heir. Unless you want to volunteer, that is."
"No thanks," the Mayor said. "I don't trust my decisions all that much."
"I understand," Henry sighed. "Let's call it a night, Mayor. Something tells me we'll need all of our energy to put up with Oogie Boogie tomorrow."
Present
In his life, Oscar Bogart was a philandering turncoat who was little more than a coward on the inside. In his after life, well... he didn't change all that much. The Mayor and I were the only ones patient enough to put up with him on a day-to-day basis. Luckily for us, help was on the way. Of course, that was bad news for the one who would provide it- Doctor Frederick Finkel.
— Henry Cadaver
