For me, it’s either the Matrix or Pulp Fiction. I have seen both a lot of times but certainly not more often than say a dozen times.
“The thing” is always a great watch and worth coming back to.
Ghostbusters. Saw it hundreds of times as a kid. Still watch it every few years.
Man of Steel
Without a doubt “Monty Python and the Holy Grail”.
It’s only a model.
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Everytime it was on.
Or came up in my /r/fullmoviesonyoutube feed. Which reminds me, we need that community here…
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Lost Horizon (Frank Capra) and Freaks (Tod Browning)
When I was a kid, Mrs. Doubtfire and The Santa Clause. I don’t rewatch movies as often as an adult.
Superbad
The Dark Knight.
Groundhog Day, Wedding Crashers, Zombieland and then 2 odd Disney movies would be Luca and Coco
I bet it felt like Groundhog Day watching that film over and over.
Star Trek: First Contact
Not a movie but Band of Brothers is on top of the annual revisit list for the past 15 years
Closely followed by 5th Element & Starship Troopers
Just Because I didn’t see it mentioned:
The Good, the Bad, the Ugly and Tombstone
For me it’s Casino. Easily my favorite movie.