Both have knowlege on eachother
To the death or knockout
Fight takes place in a graveyard
I'm leaning towards Dean. Ash wasn't born to a monster hunter as well as raised to do that very same thing. Dean's got the testicular fortitude to face down Lucifer and demand things from Angels. Also, Dean's a pretty good shot with his M1911 and generally has a shotgun or two on him. Plus, given that he has full knowledge on Ash, he should be able to take him down.
Tough fight for both have come back from death, killed a crap load of monsters, both can take alot of pain in fights, resourceful, inventive, and are lucky as hell when they are backed into a corner.
Dean has faced bigger fish, but Ash has a lead for magically making weapons appear out of thin air.
Ash has toon force durability, any amount of blunt force punishment is laughable to him. If this comes down to a fistfight he will undoubtedly win. With prep this is tricky, but since this is essentially gonna be a gunfight... hm. Both are crack shots... I honestly am not sure. I think Ash out of greater willingess to kill a normal person, will win. He showed very little care for human life in Evil Dead, once he started losing it he just shot people down with no pity or remorse. I'll go with Ash. Hail to the king, baby.
So I'm watching Supernaturals season 2 Episode Hollywood Babylon...and they are making all of these Evil Dead references...there's even a "character" named Ashley, then towards the end of the movie there's a trailer for the "horror movie" Hell Hazers II....it's Evil Dead all over again, I love it! I have to be realistic though....like somebody pointed out Ash was just thrown into this hunter lifestyle. It's in Dean's blood to hunt and kill all things supernatural....so why would this fight even be going on? They would totally respect each other.
Dean is more skilled, but Ash has more strength, arguably, more speed, and his biggest advantage is his durability. He is able to get whacked around by an immortal, who was going all out against him and can easily snap people's necks, at an old age. And that's not even his best durability feat. His best is TANKING A BLACK HOLE. This is why Ash is stronger and more durable, he was durable enough to tank it, and somehow strong enough to pull his head out of it. Black holes are strong enough to even pull light, so it's ridiculous he could pull his head out. Ash absolutely curbstomps
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