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What movies are worth rewatching?
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Donnie Darko
Fight Club
Pulp Fiction
All three of those make much more sense the second time around.
In general, though, that's a matter of personal preference. I will never turn down Young Frankenstein, The Blues Brothers, Blazing Saddles, Groundhog Day, or The Princess Bride.
You make a good distinction. In my opinion this question can be answered in two ways:
A movie that holds up being just as good on a rewatch.
Movies where you either pick up on clues/details on further rewatches once you know the full movie. Or that are just so dense/layered that you just can't catch everyrhing the first time you watch it