So pennywise can't technically be taken by the entity? he wouldn't surrender either

It's just lore, they'll find a way to make the framing device fit whatever they decide they want to add.

The Entity is a "Dark Powers of Ravenloft" kind of deal -- it's intentionally vague so it can be whatever they need it to be.

I think the distinguishing point is that all the killers so far have been ordinary humans or monsters. Basically physical beings. To my understanding, Pennywise, like the DBD entity, is essentially a kind of Lovecraftian horror. While he can take a physical form, his existence is metaphysical. It goes beyond the supernatural, both of them are more like gods. That's why it's difficult to see how one could fit in with the other lore-wise without compromising the essence of their character.

"I bet you'd suck at this"

- The Entity, 20 minutes before a very drunk Pennywise accepts a humiliating challenge from an equally drunk spider buddy.

If that was the case then children would have to be added to the trials. And penny wise only preys on kids. So the adults would be useless to kill since he needs fear. And I doubt a child knows how to repair a generator or survive being on a hook

who's to say the entity and it can't make a deal. they both get an infinite source of food through trials so the entity could offer that.

no, pennywise will not enter the game.

I know this thread has aged but I'm gonna put my two cents in.

I saw something in this thread that....just isnt true. "Pennywise is stronger then The Entity"

Yes Pennywise is an Interdimensional Alien that feeds off of fear and transforms into the worst things imaginable. But here is the thing The Entity is also a Interdimensional Creature, but this one can displace powerful creatures from all time frames throughout the universe. From the dream realm to the upside down. Not only that but it has created it's own Dark universe using memories from broken minds to make torture maps for a endless sick game of cat and mouse where it feeds off of the hopeless nest and pain of the victims of each "trial" unlike pennywise who has a feeding cycle with a measurable gap inbetween each cycle. Time obviously works diffrent in the Realm of the entity so let's say Pennywise does get dragged in. I would say one of three things happen.

1. We know the entity can be Displeased, Please, and even Inpatient. However these are things that can be felt by any creature even ones with no emotion as these things arnt feelings but mindset. We have no clue if the entity can be afraid or not. If it cant be afraid then pennywise has no power AT ALL to go at it, and would easily surrender to the entity opting to live. Just like when the loser club was winning and he made the deal saying "ILL KILL ALL OF YOU...OR...I TAKE JUST ONE, THE REST OF YOU WILL GROW OLD AND LEAD HAAAAPY LIVES" he is absolutely willing to submit to specific terms to continue living. In the end pennywise is a coward in his own right valuing his own existence rather then ever completing a mission. So he would submit to the will of the entity, unhappy he would he doing so but submits nonetheless.

2. He would automatically accept the entity's grasp seeing just how much fear exists In this new place for him to feed on, and with such a F'ed sense of time he could feed endlessly but still not as much as the entity. The entity remains more powerful as the more afraid they are for pennywise to feed off the even more hopeless they are for the entity to feed from. Leaving the Entity always just out of the pennywise power ranges.

3. This last one is a little more Complicated. We know Pennywise is an Interdimensional alien, however we have no Book, Film, Lore, or Author information about him being able to travel ON HIS OWN outside of the dimension. He just stays in the one dimension with the title Interdimensional because he HAS been in another one of steven kings shared multiverse for a short time. So the entity could see how pennywise works from his realm and easily decide to put pennywise in a pocket dimension kinda like he seemingly has to the Man in the library of the Archives. Kept in this seprate dimension where the time works the same as the rest of the realm the seconds are like years and the seconds add up. Eventually with some minor difficulties. The entity would break pennywise with the threat of Starvation. Keeping pennywise weak. When the entity broke him pennywise would agree and do a few trials to feed and gain strength where the entity would throw him into that pocket dimension again to make sure pennywise starved longer always feeding him enough to keep him alive but never letting him get strong enough to pose even the slightest bit of a threat.

The entity is Obviously Omnipresent throughout the Multiverse as he drags the Horrors of all universes and the strong willed survivors from all universes after watching each universe as well as his own realm and other realms from the upside down to the dream realm to the spirit realm to the material plane etc. He is all knowing and seemingly all powerful.

Pennywise is nothing compared to this Monster, this Puppetaster...

This entity

well there’s the demogorgon which was never human and never had a past self. At least pennywise has shown some fear and vulnerability. I think he fits more than the demogorgon.