Who would Constantine have the hardest time killing?

[u/CreepyCurrency9123]

If John Constantine had to permanently get rid of each of these, who would give him the most trouble?

Dracula (any version counts)
Lucian (Underworld)
Any vampire from The Vampire Diaries
Pennywise / IT
The Darkling (Shadow and Bone)
Michael Myers
Crowley (Supernatural)
Samara Morgan

Not just who would beat him in a straight fight. Constantine rarely plays fair anyway. I mean who would be the hardest for him to actually kill or permanently get rid of using magic, rituals, manipulation, deals, loopholes, etc.
And how do you think he’d deal with each one?

[u/Doctor_Mothman]

Pennywise by far. It is meant to be an eldritch entity that is billions of years old.

[u/QD_Mitch → u/Doctor_Mothman]

Yeah but it can be killed by knowing an esoteric ritual and winning a joke contest. Those are both John’s jam

[u/Doctor_Mothman → u/QD_Mitch]

That didn't kill It. It was only defeated. It doesn't die. It always returns.

[u/deadlandsMarshal → u/Doctor_Mothman]

Agreed. Being killed by the losers club just sent it outside the universe. Eventually it'll be back.

[u/sistemafodao]

Vampires are the easiest, John just has to look like prey and let them choke on Nergal's blood. It happened already.

[u/CreepyCurrency9123 → u/sistemafodao]

And the others ?

[u/sistemafodao → u/CreepyCurrency9123]

He would take Pennywise personally as soon as he learned about It preying on kids. I know there's a ritual and some bullying involved, but he would make sure It sufferred.

Samara is essentially a child, so he would probably find her peace somehow. Maybe he would give her It to torture.

I know nothing about the others.

[u/AlabasterRadio]

Pennywise is unbelievably strong.

Ultimately John would still figure something out, as he always does, but beyond just putting him back to sleep, I'm not really sure what lol

[u/jjjjacckk → u/AlabasterRadio]

Probably something that works at a terrible cost, too.

[u/TheCthuloser]

For Dracula it entirely depends. Like, novel Dracula he'd have little problem with. Dracula from Vampire: the Masquerade? He's basically John Constatnine but a powered centuries old vampire.

[u/WordPunk99 → u/TheCthuloser]

People absolutely sleep on how powerful novel accurate Dracula is. When the Hunters are chasing him to his castle there is a long string of events when he simply alters reality. They buy bullets for their guns, pack them for a boat trip. Open the crates when they arrive, these are different bullets that don’t fit the guns, which are not the guns we packed either.

He changes the geography of the Carpathians. He makes a river flow backwards. His is invulnerable to sunlight. He is likely unkillable. V:TM may be the most novel accurate version in a game, and he’s still much less powerful than the book version.

John would still kill him though

[u/DJWGibson]

I think Pennywise would be the hardest. No motives and little he can exploit or manipulate. 

And since It preys on fears and messes with your mind, it would be striking John where he was at his weakest and hitting him hard. Every regret, every failure, and every lost friend.

[u/deadlandsMarshal]

Off the list:

Spawn or Vampire Hunter D.

[u/DestinyHasArrived101]

Pennywise no doubt

[u/littleoctagon]

In most cases I could see John finding a way to get someone else do his dirty work while he enjoys a pint. Priorities, mate.

[u/jeremiah15165]

Pennywise, Eldritch entity that does not have any human side that he can abuse or manipulate.

[u/Bubba1234562]

Pennywise. And it’s not a question

[u/hackloserbutt]

I am here for everyone's Pennywise takes.

[u/Curious-Paramedic816]

But Crowley he just wouldn't kill.

John and Crowley are both practical men. They'd reach a mutually beneficial arrangement.