Pennywise vs Sam is a what-if death battle between Pennywise from It and Sam from Trick 'r treat
Description[]
Wiz: Fear, to many people it's just a simple emotion.
Boomstick: But then there are some who use it as a weapon, like Pennywise the dancing clown.
Wiz: And Sam the trick or treating demon.
Boomstick: He's Wiz and I'm Boomstick.
Wiz: And it's our job to analyze their armor weapons and skills to find out who will win a death battle!
Pennywise[]
Wiz: In the small town of Derry, Maine, a creature so menacing was lurking and stalking the citizens of the seemingly peaceful township.
Pennywise (1990 version): Hi Georgie!
Boomstick: A clown!? You really expect me to be afraid of a clown?
Wiz: Yes, Pennywise is a ferocious shapeshifting monster who appeared in Derry before the dawn of time and has been terrifying the town ever since.
Boomstick: Holy shit!
Wiz: He may not look like much, but Pennywise is a fear master, able to get inside his prey's mind and feed off of their worst fears.
Pennywise (2017 version): I'm not real enough for you Billy? I was real enough for Georgie!
Boomstick: Pennywise uses his fear manipulation to literally feed off of everyone's worst fear. Although he can go after anyone he wishes, his preferred prey is children because they are easier to scare.
Wiz: This is all thanks to his shapeshifting abilities. He can easily transform himself into a werewolf, sharks, a school of piranha...
Boomstick: The fuck?
Wiz: And even a swarm of flying leeches.
Boomstick: The double fuck!?
Wiz: His ultimate weapons however are the deadlights, which can drive a person insane, leave them catatonic or even kill them. Even though he is a fear master and uses shapeshifting skills a lot, Pennywise does have his own attributes without them.
Boomstick: Pennywise nearly wiped out all of Derry with a massive hurricane, survived an explosion that nearly destroyed the planet and killed people without anyone's knowledge for eons, literally getting away with murder. Is there anything that can stop this circus bastard?
Wiz: There are a few things. For one, he often underestimates his opponents believing that nothing can kill him. He also needs to feed once every twenty-seven years or else he'll literally starve to death. He also has a fear of the turtle, who created the universe.
Boomstick: ...That has got to be the most ridiculous thing I've ever heard.
Pennywise (1990 version): Yes Georgie... they all float... and when you're down here with me... YOU'LL FLOAT TOO!! *grabs Georgie's arm and proceeds to kill him offscreen as Georgie screams in terror*
Sam[]
Wiz: Halloween is a holiday full of treats and many tricks.
Boomstick: But the holiday has three rules; Hand out treats, wear a costume and never blow out a jack-o'-lantern. Disobey one of these rules and you'll be visited by the pint-sized demon named Sam.
Mr. Kreeg: Who the hell are you..?
Wiz: Named after the Celtic holiday Samhain, Sam takes it upon himself to uphold the traditions of Halloween. Those who break tradition pays the price.
(A woman named Emma is slaughtered by Sam and her decapitated head is ironically used as a Halloween decoration)
Boomstick: Even by demon standards, that is fucking gruesome! Sam's powers are usually standard teleportation and telekinesis, but he also has shapeshifting abilities, necromancy and the ability to reattach severed limbs.
Mr. Kreeg: (sees Sam's severed hand come to life and leave the room) You've got to be fucking kidding me...
Wiz: He also has his makeshift lollipop that he can turn into a blade should he need to kill up close and personal. His powers alone allowed him to gain attributes of his own. He can survive three shotgun blasts to the head, chest and arm, tackled a full grown man and helped an autistic girl get revenge on a group of kids who pulled a prank on her.
Boomstick: With that in mind, Sam I am does have his own flaw; turns out he can only kill someone who break tradition and will leave anyone who doesn't alone. So if you're following the rules, you're good.
Sam watches as Emma blows out a jack-o'-lantern, looks at his lollipop and runs across the street
Battle[]
Twenty-seven years pass and a monster roars as it awakens. Meanwhile Sam, after massacring twelve people for breaking Halloween tradition, reaches into his bag and grabs a jawbreaker. He suddenly loses the candy and it falls into a sewer grate. Sam peers inside and sees It under his Pennywise persona approaching him.
Pennywise: Hiya Sammy! Do you want your jawbreaker and maybe a balloon?
Sam thinks about it then excitedly nods his head. He reaches inside the sewer grate for his jawbreaker and a balloon, but Pennywise grabs his wrist and drags him into the sewers with him.
Fight!
Sam kicks Pennywise in the face and angrily bites down on his lollipop, turning it into a blade. Pennywise grips the wall with his fingers and transforms himself into a horde of locusts. Sam swats at the locusts, killing several at a time. Sam teleports away and grabs his candy bar knife and throws it at Pennywise's neck. The demon jumps from the platform he was standing on and kicks the knife deeper into the clown.
Pennywise: Oooh! I needed some acupuncture for a while!
He then transforms into a swarm of flying leeches and the knife drops harmlessly on the ground, to Sam's confusion. Pennywise transforms back into his clown persona and kicks Sam to the ground. Before he could deliver the final blow, Sam uses his fear manipulation powers to show Pennywise his worst fear. The clown suddenly sees the turtle coming towards him, causing him to cower in fear. Pennywise then sees something behind the turtle.
Pennywise: What the..?
He sees that the turtle's legs were moving inconsistently and uses his own fear powers to make the illusion disappear, to Sam's shock. The demonic clown then transformed into a werewolf and slashes at Sam's head, ripping off his mask in the process. Sam reveals his skull/pumpkin face and screams angrily at Pennywise.
Pennywise: Okay... that's comedy...
Sam uses his necromancy to raise six dead children and have them attack the clown while he slashes at him with his lollipop blade. Pennywise, clothes torn and bloodied and exhausted, backs away into a corner and raises his hand up to Sam.
Pennywise: Wait, let's talk about this for a second. Having all of these bastards help you? That's no fair, is it?
Sam halts his attack as Pennywise coughs up blood, apparently starving from lack of fear.
Pennywise: It was only the two of us, a fight to see who is the master of fear. Now that you have help, it's no fun anymore right?
Sam thinks about it for a moment and agrees with Pennywise. He holds the clown up by the neck and prepares a killing blow.
Pennywise: Just one last thing, capiche? Sometimes the best victories are the ones you don't see coming!
Pennywise suddenly opens his mouth and reveals the deadlights to the demonic guardian of Halloween, leaving him catatonic. Pennywise then transforms into a bloodthirsty ape and rips and crushes Sam's head, transitioning between roaring and laughing.
KO!
Boomstick: Halloween, we're going to need a guardian!
Wiz: This was a close call. Both Pennywise and Sam easily countered each other with their respective powers, whether or not they were perfectly affective.
Boomstick: So the deciding factor was durability and experience. As said before, Pennywise was durable enough to survive a cataclysmic impact that nearly destroyed the earth and didn't even flinch. Sam's only known worst thing he had to endure were three shotgun blasts to three parts of his body and he was unconscious after that.
Wiz: Pennywise's experience also trumps Sam's since he was literally born before time began. But most importantly, the deadlights can leave anyone who looks at them insane, catatonic or dead. Once Pennywise had Sam in his sights, it was only a matter of time before he delivered the final blow.
Boomstick: This clown definitely is the king of fear and tradition.
Wiz: The winner is Pennywise.