>>223816789
Depends on if Chuck is the God of the battle's universe. If Chuck is God, they rape anyone or anything in under two days maximum, no matter how improbable. If Chuck isn't God, however, they very well could lose against someone like Pennywise (although I personally would still bet my money on the brothers in the Pennywise matchup).

>>223816957
This. Everything they do throughout the entire show is purely because Chuck deemed it to be so. They are nothing without him, as evidenced by how it ended.

>>223816789
They have weapons that kill gods and devils, I love Jason but he's completely fucked. Jason X might stand a chance as most of him is covered in metal.

>>223816789
Are you talking about Demon-Dean Winchester with the Mark of Cain wielding the First Blade, fused with Righteous-Soul Purgatory-trained Dean, carrying the Colt (loaded with original bullets) and the Equalizer (The Gun made by God), wearing the Amulet of God-detection, possessed by Alternate Universe Archangel Michael while retaining full consciousness and control, infused with Grace, wielding Ruby’s Demon-Killing Knife and an Archangel Blade, boosted by Vampire-blood augmented reflexes, having performed the Cain Slayer Mark transformation, and backed by Death’s Scythe.

...ALL OF THIS paired with Gadreel-possessed, Demon-Blood-jacked, Soulless-Sam Winchester who completed the Demon Trials, wielding the Book of the Damned, fully attuned to Witchcraft spells from Rowena’s Codex, possessing psychic telekinesis and exorcism-by-mind-control, infused with Jack Kline's cosmic Nephilim Grace, brandishing an Angel Blade, protected by the Enochian warding carved into his ribs, and wielding the power of God-Sam after siphon-absorbing the divine essence of Chuck Shurley (God Himself).

And I'm referring to Dean and Sam Winchester who have dying-and-resurrecting immortality (having returned from Hell, Heaven, Purgatory, and time loops hundreds of times), backed by The Impala ('67 Chevy with trunk warding and weapons cache), possessing Gedou-level Anti-Possession tattoo protection, with Castiel (God-stuffed or Archangel form) as their personal summoning summon, empowered by The Darkness / Amara's personal favor, and possessing canonical Protagonist Plot Armor explicitly granted and revoked by the Almighty creator of the multiverse!

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>>223816789
>Sammy sacrifices himself
>Dean beats Jigsaw to death

>>223816789
Scenarios like Obsession, Weapons, Insidious, Annabelle, Lights Out, etc. would be pretty trivial monsters of the week stuff for them.

>>223816789
As another anon said, they're literally walking plot armors so they win against all of them. Even if they get killed as they did many times, they'll come back anyways and finish the job.