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Notes -
You know, I generally agree with you, but in fact Bear's buddy wishes for a million dollars and it comes in stacks of hundreds falling harmlessly from the ceiling, which complicates the monkey's paw claim.
Giving someone a billion dollars will turn them into a demonic asshole a lot quicker than any dark magic.
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I would chalk it to either an angler fish strategy, or the OWW having a sense of dramatic irony.
Since there are enough OWWs in the word that you can see other people's wishes granted, maybe the OWW lures people in by granting a subset of wishes not touching on human agency in a completely straightforward way. That way, it generates positive word of mouth and gets more people to use it for the kinds of wishes it likes to corrupt.
Alternatively, maybe the OWW just knew with high probability that the guy would never get to use the money because of Nikki, so it was happy to grant the wish for the dramatic irony his death would produce.
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I may be misremembering the movie, but didn’t Bear’s friend go to Bear’s house to brag about the money then immediately get shot by Nikki? That sequence of events was caused by the money, and would be a monkey’s paw.
In the original Monkey's Paw, it gets them their money by killing their son. I wouldn't consider a perfectly-fulfilled wish with bad consequences to be a Monkey's Paw.
It's the difference between:
A: I want a Porche 911 here right now!
Genie: Okay! Vroom, Smash!!
and
A: I want a Porche 911 here right now!
Genie: Okay!
(After years of enjoying it, his aggressive driving led to a fatal collision)
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Difficult to say. Certainly I'd say that it wasn't "caused" in the same way that Bear's wish caused Nikki to become possessed. If we're stipulating that there's no free will in the Obsession universe and Ian could not have chosen otherwise but to go brag about the money when Nikki was home and therefore get shot then that has some significant implications on Bear's culpability and questions about monkey's paws and what caused what become somewhat moot - the whole sequence of events was predetermined anyway.
Im a believer in compatibilism, so I don’t think there is a contradiction between determinism and free will. My personal headcanon is that any wish from the one-wish-willow either directly causes something bad, like Nikki’s possession, or indirectly causes something bad like the above sequence Friend gets money -> Friend goes to brag about it -> Friend gets shot by Nikki.
We are getting into death of the author territory at this point, so this is just a personal rationalization of the mechanics of the movie.
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My personal interpretation is that the One Wish Willow cared more about screwing over Bear than Ian, because he had more to work with psychologically, but also it knew that Ian was doomed anyway because he'd wander into Bear's house minutes later. But it wouldn't be in-character for the One Wish Willow to kill Ian by dropping money on his head, anyway, because it's demonic, it cares about corrupting the soul; if it's going to corrupt a wish for money, it's going to do it by provoking further doubling-down on avarice.
So no free will in the Obsession cinematic universe? Difficult to assign blame then, or discuss whether the genie is an asshole.
This btw seemed a very weak part of the movie - Bear has already seen the money, wtf is Ian barging into Bear's house for?
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