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Since Joker has 1 years of prep what stops him from literally getting some nuclear weapons and....nuking Derry or something like that? or maybe create some kind of Joker Venom weapon,also he's very smart and unpredictable due to his insanity,i vote Joker via his intelligence,being unpredictable,and skills in combat.
It's worth mentioning, Pennywise isn't just gonna sit there and wait for Joker to come to him, he's gonna use mind manip and social influencing to make Joker's prep worse- Not that I think it'll have much effect on him. However, he might simply use Memory Manip to outright have him forget he's supposed to prep at all.

However, this is a stomp, since the OP doesn't specify Pennywise's key, and Joker should have no way of hurting the Deadlights- Bravery weakens him, but I'm not sure if it's enough to kill him.

I think we should think about this a bit more before voting, unless I'm missing something.
I mean, Pennywise can't affect you at all if you aren't even a little afraid of him in the movies, or at least that was what I understood after watching IT Chapter 2. The kids literally beat him by making fun of him, they didn't have Gan helping them or anything so Joker can definitely win easily. Joker isn't afraid of anything.
Joker has been afraid multiple times in the comic books, just as many as he's been completely unafraid of incredibly scary stuff, he's not exactly consistent in this. But fair enough, I don't think he'd be scared either... Hold on, what if Pennywise copied Batman, and started having him act in a murderous way? I think he could find some sort of Batman-related fear.
I don't think he'd be scared. One of Joker's main goals is to prove to Batman that all it takes is one bad day to be dragged to his level and he wants to see Batman kill. So I can see one of two things happening: Either he starts laughing because a murderous Batman would be funny to him, or he gets pissed off because it was spoiled for him. I'm thinking Joker gets pissed because that's his beef with Batman Who Laughs in the canon comic.
Looking it up, some of the ways the Joker has been scared are:

Being irrelevant or losing his reputation, in a (non-canon, obviously) cartoon episode he's scared of being killed by a random goon and being forgotten. This also is in Arkham and other things, none of them canon to the comics obviously but it does make sense.

More interestingly, I found some stuff about him being scared of Batman dying, after all that leaves him with no purpose.

... Anyway, I don't think either of these would be easy to exploit for Pennywise. Gamer probably wins this.
I know this is 5 days ago but i don't think Joker really needs to fight Pennywise directly,if anything Joker could use one of his disguises and then strike at the right time.
Normally we couldn't add this cause of the whole Forum move thing, but the thread *was* over before that happened. I'm not sure if we can
Armorchompy said:
Normally we couldn't add this cause of the whole Forum move thing, but the thread *was* over before that happened. I'm not sure if we can

Thankfully, this was made before the 14th of April, so i think it might stay on the wiki..
In case you were all wondering, this was base Pennywise.

My apologies for taking a while to answer some questions. Anyway, can this be added or nah?
Joker obviously. He can't be scared (unless its the IRS). If Pennywise can be beaten by a kid named Richie with a baseball bat simply by NOT being scared, then I can see Joker being able to do the same thing. His Joker gas has been able to affect non-human/superhumans before, so Pennywise can be affected by it as well.