Who wins: Randall “The Walkin Dude” Flagg v. Pennywise

I prefer The Stand over It but Flagg did seem to have some blind spots so probably Pennywise.

I know Flagg is also in some of King's Dark Tower books which I have not read so I don't know how if he had some abilities in those that would change that

He’s the primary antagonist in the dark tower. He’s a powerful dude, but he’s still a dude with the backing of some demonic entity. Whereas Pennywise is a demonic entity. So Pennywise probably wins pretty easily

Would rather see Pennywise vs these guys

quote:

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A bunch of kids were able to beat Pennywise in a sewer by running a train on the girl in the group. It took a nuke in downtown Las Vegas and the sacrifice of 3 of the good guys to settle Flagg.

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Good rebuttal, it exposes a point many seemed to miss and that's weaknesses vs strengths.

Flagg:
--Strengths: Magic/Sorcery (can cast spells to manipulate reality and shapeshift to a small degree and teleport), psychic influence (manipulating others and then controlling them through charisma and/or fear), high durability (possible immortality) and the ability to identify and exploit psychologcal vulnerabilities.

--Weaknesses: Arrogance (underestimating his enemies), limited physical combat ability (relies on his powers more than brute strength) and vulnerability to divine powers (such as an inability to control Mother Abagail's followers, the glowing "Hand of God" which detonates the warhead in Las Vegas or his failed attempt to kill Roland as Roland's purpose is divinely ordained).

Pennywise:
--Strengths: Shapeshifting (can take virtually any form, often embodying its victims' worst fears), psychic dominance (induces hallucinations in order to create the fear upon which it feeds), strong reality manipulation (being able to alter portions of Derry), physical strength and near-immortality.

--Weaknesses: Dependent on the fear of others for strength (when victims overcome the fear, it is significantly weakened) which seems to have a cumulative component as group fearlessness can be even more harmful to it and being a cosmic entity it seems to be bound by certain cosmic rules.



The fight:

-Putting this fight in a neutral area (not Vegas, not Derry, etc) with no prep time, the fight goes to Pennywise as he seems to be a higher order being.

Pennywise seems to be at least on the order of the Crimson King (to whom Randall Flagg is subservient). Along with that, his greater ability at reality manipulation, his far greater physical strength and his probably stronger psychic defenses should be more than a match for Flagg in most settings. For Flagg, the keys to possibly winning would be fearlessness (to not feed Pennywise) and using his teleportation and magic to keep Pennywise off-balance until he could find an opening. That would be only if his arrogance wouldn't cloud his judgement.

Flagg is the Devil on Earth. Pennywise is just an alien. Hell, Pennywise probably ends up as Flagg’s pet.