The Last Dragon or Ghostbusters, probably. I still watch those both at least once a year. So probably 50+ times for both of those.
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American History X, Pulp Fiction, Heat.. I could go on and on
The original Matrix movie
Definitely the Avatar movie, I mean the blue ones not TLA. I watched it when it came out, watched it several times with my family and friends. Lastly I watched it at IMAX, was a fantastic experience. Sadly second movie did not live up to my expectations.
There are few of them for me, but maybe Warrior (2011) is the favourite go to movie for me. If I'm overwhelmed by anything, it helps me reset myself and put things in perspective and get me in the mindset to fight back and stay strong.
Maybe Thor Ragnarok
Alien, Aliens and Predator. The Big Lebowski and the John Wick films are gaining traction more recently.
For me it Lord of the Rings and/or Harry Potter. Can't count how often I watched these masterpieces.
Practical Magic. It might be tied with Nightmare Before Christmas.
It was comfortable for me to watch them both often when I scored a VCR in my room.
Star Trek: First Contact or Insurrection
Hateful Eight. The acting, pacing, dialogue all 10/10 IMO. It just feels cozy watching it.
For me it's Casino. Easily my favorite movie.
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.
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
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
The fast and the furious 1,2,3
Shaun Of The Dead
Pee Wee's Big Adventure as a child and too many Michael Bay Transformers sequels as an adult due to their frequency on FX and now Pluto TV. I think Dark of the Moon is aired most often.
For me American Pie (was the first movie I've watched in English, when I was finding out you could switch languages on dvd), followed by the Matrix.
The Batman. Dune