The Lord of the Rings
The Big Lebowski
Hot Fuzz
I watched that movie stoned off my ass and with the catchphrases the characters do, I thought I was in a time loop. 10/10
Also adding Shawn of the Dead/anything Edgar Wright
Everything Everywhere All at Once, Interstellar, Fight Club, Arrival, The Sixth Sense, Primer. I’m sure I could go on but all of those are great on a rewatch.
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:
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A movie that holds up being just as good on a rewatch.
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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