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Not completely by my own choice, but I feel like I've seen National Lampoon's Christmas Vacation - at least in part - once or more per holiday season since it was released.
The same is true of Elf, but obviously that movie is quite a bit more recent.
For movies I've watched the most by my own choice, it's probably the Kill Bills or Inglorious Basterds, but those have got to be way behind in raw count. Goonies and the Back to the Future series probably have honorable mentions because of how long they've been around and continue to be a fun watch.
Good call! I'm not big on rewatching movies, but I definitely see Christmas Story, Elf, and Christmas Vacation every year, so I've probably seen A Christmas Story more than any other movie in the past 40 years.
Runner up might be having Disney's Robin Hood on repeat when I was about 6. Oooda-lolly!
Shit, I was gonna say three way tie between Spirited Away, Eternal Sunshine of the Spotless Mind, and 21 Jump Street, but if I count what I've watched at school then National Treasure wins lol