Why choose a lesser evil?

This story (Jeff the Killer vs Laughing Jack round 1) involves Jeff passing out drunk, having a weird dream, and waking up to meet laughing Jack. It's an extremely weak encounter. Laughing Jack says that he has seen Jeff's murderous activities that day (I guess Jeff kills someone everyday in this story) and he's mad about it. Not that it's explained why. This could have been a territorial thing, but instead it just has Jeff stabbing Jack repeatedly, and dropping a one liner. The end.

Continuity: I'm considering this just a drunken dream.

Battle stats: None to speak of. Jeff defeats Jack through the power of one liners, and knife-y stab powers.

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"There is only room for one of us."-- Laughing Jack

And now lets swing the other way entirely. (Laughing Jack vs Jeff the killer round 2) This story opens with Jeff killing someone, which is his whole character. Jack on the other hand has found a new kid to befriend before killing. I will say this story offers some character descriptions at least, for those less familiar with Creepy Pasta's favorite son, and the ever popular psychotic clown... thing.

Convenience abounds when Jeff takes to killing in the same city as Jack. And more specifically, the same house. Which Jack takes exception to, having staked out this family for his own sadistic pleasures.

Jeff doesn't even get a hit in as Jack teleports behind him, and slammed him into a wall, then squeezed Jeff's wrist till it cracked. Then to add insult to injury he tossed Jeff out a window. No introductions are made as Jeff's reputation seems to have preceded him. Jeff isn't surprised at all by Jack's supernatural abilities, but that is believable if this is canon with Jeff vs Slender Man

It's strange that the police seem to have heard about Jack. If anyone had survived an encounter with Jack, I doubt the police would believe it anyway.

Round 2 of this fight has Jeff circling the neighborhood, and just so happening to find the house of Timmy's grandmother, and sees Jack through one of the windows. Jack did his thing of making kids love him with free candy, before killing Annie in a brutal manner. But he doesn't get to kill Timmy because Jeff has beat him to it.

This time Jeff stabs Jack with a knife toss, but gets tele-pawned again. Jack throws him across the room, then knocks him to the ground, first dislocating Jeff's shoulder, then ripped the arm loose altogether. At this point it stops being a fight and becomes a joke as Jack beats Jeff with his own severed arm.

It should be noted that Jeff's supposed pain resistance is absent from the story.

Continuity: This could canon, but only if it is the last Jeff story ever, since I don't believe he can regenerate an arm.

Battle stats: Jack displays speedy reflexes, and superhuman strength. Though his originality in kills were unimaginative, except for filling Jeff's corpse with butterscotch candies.

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“You have no idea clown, how long its been since I had a real fight. This is going to be fun!"-- Jeff the killer.

But the fight isn't over yet sports fans. (Jeff the killer vs Laughing Jack round 3) In an unnamed small town, that is also apparently Jeff's home town, Laughing Jack has come to play his violent games. This is lucky since Jeff is in the mood to rumble, and is thinking about his past fights with Jane, and Slender, and the Rake.

They engage in some incredibly weak smack talking, and by weak I mean bad. Jeff takes a stab at Jack, who teleported behind Jeff, then swung a baseball bat at him. Jeff ducks and stabs Jack in the hip, and this time it works. Jack seems surprised at this, but he shouldn't be as he has never been an immaterial being. Jack taunts Jeff, then knocks him out with the bat.

Jeff awakes in an abandoned amusement park, complete with decrepit park attractions, an old circus tent, and of course the dismembered bodies of Jack's past victims. Jack brings the dead children to life to attack Jeff, but most of the zombie children just wander about aimlessly. So maybe not the best power Jack has ever exhibited.

Jeff uses a severed zombie head to knock Jack from the trapeze. Stunned from hitting the ground, Jeff kicks him in the stomach hard enough to make him cough blood. Jeff stabs Jack again, but this time it has no effect. Jack swings his bat again, but Jeff snatches it away and smacks Jack in the head again. But as he goes for the killing slash, Jack teleports away with one last taunt.

Jeff passes out again, and wakes up in the ally again, vowing revenge.

Continuity: This may be canon with Jeff the killer vs Pinkie Pie, but not with the mainstream Creepy Pasta U.

Battle stats: Jack shows more vulnerability then other fights, but compensated with the ability to teleport his opponent, and raise revenant children.

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"Wow, this will be more fun than I thought!"-- Laughing Jack.

(Jeff The Killer vs Laughing Jack round 4) Another story that starts with Jeff tired out from a hard day of serial killing. He falls asleep and finds himself in a creepy dream carnival. This is similar to the scene from the last story, which raises interesting questions. Jack seems to know Jeff, but if he's in Jeff's mind, then I suppose this isn't so strange. Jack says he's coming for Jeff, but before he can deal a death blow Jeff wakes up.

Jeff gets up and goes for a walk, and slaughters a family with ease. But as he goes to kill the last kid, he finds they have been killed and disemboweled. Jeff returns to the shed he is staying in, and struggles to stay awake, having surmised that Jack is a sleep-killer now. Jack manipulates reality to make chains appear and tie up Jeff to the couch, but instead of killing Jeff he makes weak villain taunts. Just as he is about to disappear Jeff breaks free and grabs Jack, and is taken to the creepy dream carnival.

Jack teleports behind Jeff, and kicks him to the ground. Jeff manages to find a crowbar, and uses it to wipe the smile off Jack's face. Jack teleports again, slashing at Jeff's back with his claws. Jeff slammed his elbow back into Jack's face, but Jack slashed Jeff's face with his claws, then drives a knee into Jeff's face. Finally, after some taunting, he kills Jeff by stabbing his claws into Jeff's stomach.

Continuity: This one is actually plausible. Yes, Jeff dies from his wounds (apparently) but the story does end with the rumor of Jeff returning to killing. Whether it really is Jeff, or a copycat killer is unknown. But slashers do have a history of returning from the dead.

Battle stats:Once again Jack uses teleportation to his advantage, and he is shown to be dangerous with just his claws. Jeff is shown to be capable with improvised melee weapons.

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"Whens the bullsh*t going to end?" --Jeff the killer

(Laughing Jack vs Jeff the killer round 5 audio log only.) Once again Jeff is tired after a long day of murder and mayhem, and has fallen asleep in his childhood home. And he dreams of a creepy decrepit carnival, of course. Interestingly enough, Jeff hears Jack singing the song of the music box, from Candy Pop and Candy Cane. Though of course Jeff doesn't know this. But it does suggest a connection to Candy Pop & Candy Cane, if you accept it as canon to Laughing Jack.

Jeff, who has become a child in the dream, sees dozens of mutilated, dead children littering the carnival grounds. Jack raises this army of zombie children to attack Jeff, who gets mauled, but wakes up before they can kill him.

Shaken by this dream, Jeff sees Jack in the mirror, standing behind him, then smashes the mirror. Going to to find some unaware victims to kill, he begins to see children in the distance, stalking him. Becoming more and more unhinged, Jeff finds one child blocking his path, only to discover it's just a doll.

Upon leaving town Jeff feels the need to lay down, and think about these bizarre events. Perhaps he nods off, because soon he hears the carnival music again, and realizes he is back in the creepy carnival. Jeff and Jack square off, with some very nice banter, before Jack disappears.

He reappears, and the fight really begins. Jack gets a cheap kick to Jeff's chin, before running into the fun house for some fun and games. Jack appears in every mirror, and taunts Jeff.

Jeff smashes mirror after mirror, but to no avail. Jack suddenly leaps from a mirror and stabs his claws into Jeff's stomach. Before he can make the killing blow, and perhaps surprised at Jeff's ability to react at all, Jeff stabs Jack in the back of his shoulder. Perhaps even more surprised at being hurt and bleeding, Jack is knocked to the floor, and Jeff fall on the crazed clown, stabbing Jack again and again in the chest. With one final twist Jack dies, and turns to black smoke, and the carnival disappears.

Continuity: This is the only one of the lot I would consider canon. There are some odd things stated in the dialogue, but overall the fight is fairly even, and according to the original chronicler, Jack fled the fight, rather then dying. So this could very well be canon with the respective Jeff the killer, and Laughing Jack myths.

Battle stats: Jack uses misdirection to get a few blows in, and uses psychological terror to well effect. Jack also has apparent dream invasion powers, or mid-level reality warping. Jeff displays high level pain tolerance, and speed attacks.

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“Now, now we have to play nice, we don’t want anyone getting hurt now do we?”-- Laughing Jack

This story (Jeff the killer vs Laughing Jack round 6) starts out very straight forward with Jeff wandering around around some unnamed town bordering on some woodlands. Hearing strange music coming from the woods he decides to investigate, and finds an old, abandoned amusement park. (Naturally)

They exchange some bad smack talk, and Jack lures Jeff into the fun house. Once again Jeff stabs Jack in the shoulder, but in this story it has no effect. And eerily, once again Jack drives his claws into Jeff's stomach, only this time he rips out Jeff's entrails, and Jeff dies with no fanfare.

Continuity: This story bares similar elements to other stories, but canon is doubted. Probably just a retell of round 5.

Battle stats: Jack is invulnerable.

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Things to take from these battles/common elements--

Jack teleports about for sneak attacks.

Jack has either dream powers or low level reality warping power.

Jack often seem to occupy old Amusement parks/carnivals/circus tents. These may exist in the real world, or in a dream world.

Jack seems to have the power to re-animate past victims.

In none of these battles did Jack use shape shifting, but relied mostly on his claws for melee attacks.

Jeff has fast reflexes, allowing him to get a few unexpected hits in.

Some pain resistance.

Jeff shows some ability with different melee weapons.

Final conclusion:

I think Jack would beat Jeff in the real world or dream world, two out of three times.

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“Well, let’s see how much fun we can have before you die.”-- Laughing Jack

In this fight (Slenderman vs. Laughing Jack - Spinpasta Wi) Laughing Jack's box appears in a school, in a town that Slender Man has basically killed off. It's not really explained why Jack's box would reappear, or why he would be in it to start with.

There's not much in the way of dialogue, as Slender does not speak, and Jack's comments are less then stellar.

Slender Man also thinks Jack's smack talk is weak sauce and knocks through a wall, but it doesn't seem to hurt him much.

Slender Man does a Jack move and teleports behind Jack, but Jack spins around and shanks Slender with a rusted knife. Slender Man makes a strategic retreat to lure Jack into the woods. To Slender's home turf if you will.

What happens next is easily the best beat down in any cp vs cp fight yet. Slender slams Jack into the ground, and a few trees, repeatedly. Then he tosses Jack into the air, and slams him into the ground.

But before Slender can beat Jack into jelly, he cut Slender's tentacle with his trusty rusty knife. Jack decides he's tired of taking it, and deals some damage of his own with razor playing cards.

Slender drives a dozen tentacles into Jack's body, but Jack catches him somehow, and forcibly knocks him away. I assume its some sort of telekinetic power.

Jack uses the power of evil bandages to incapacitate Slender, then shreds him with more razor cards. Slender escapes somehow, and Jack decides its time to go, except Slender is pissed now, and appears before Jack no matter where he turns.

Slender wraps his tentacles around Jack and squeezes him to death, which causes Jack to revert to his colorful form for some reason. Or else Jack faked his death, since his eyes open after Slender leaves.

Continuity: Nothing about this specifically breaks established canon, so this could be canon with either characters myth.

Battles stats: Slender Man displays above average strength, shape shifting, and teleporting.

Jack displays some invulnerability, fast reflexes, the ability to use throwing weapons with extreme accuracy, and bandage control power.