As a kid I spent probably a week sitting under a table in my room, rewatching A New Hope on a portable dvd player over and over and over. I thought that I should watch it until I had every line memorized, and then move onto ESB (which I never did for obvious reasons)
So probably ANH, followed by any other SW movie, then Mad Max Fury Road and Sicario
As a kid, Tremors, Aliens, and Police Academy 4. Those were films we had on VHS (recorded from the TV). The first two were on the same 4h cassette, recorded in glorious long play mode and the write protection tab broken out for safety.
More than a dozen watches for each of those.
As an adult, there’s a few had multiple watches. No idea what’s the “most” but the ones that stick out are: Charlie’s Angels - the mid 2000’s one with Drew Barrymore, Cameron Diaz and Lucy Lu. Blade 2 The fast and the Furious The terminator Kill Bill
I used to fall asleep watching Twister on VHS. Something about the substandard quality and tracking sound really sealed the deal when I needed to catch some Zzz’s.
I watched it so many times that I wore out the tape.
Same here, must be over 50 times since 99 when it first came out on dvd. Most of those in the first few years showing off my flash new dual disc dvd player!
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