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I like your question. Never heard anyone ever ask which 5 horror movies you could have on a deserted island. Reason I say that is, although I'm a lifelong horror fan, if I could have a very limited number of movies at a deserted island, I don't know I'd take any horror. Being on a deserted island always sounds nice in one way, but honestly, I think it would pack plenty of it's own horror. :) (I know, way to take the fun out of a question!)
I agree with knifefight, rewatchability would be important. And I'd probably try get 5 documentaries on how to survive on a deserted island. If that didn't fly, I'd keep my definition of horror really wide and go for some uplifting, inspiring, musical, etc, movies like: Yellow Submarine, Gandhi, Hitchhiker's Guide to the Galaxy (BBC TV 81), Grease 78 and Jesus of Nazareth 77 (6 hrs).
If those movies wouldn't fly, I'd go for a second round:
Evil Dead 2
Aliens
Ghostbusters
Bill & Ted's Bogus Journey
Hitchhiker's Guide to the Galaxy (BBC TV 81)
If they didn't allow Hitchhicker and Bogus Journey, I'd replace them with some combo of Se7en, Poltergeist or The Thing 82.
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