if you could only watch one movie ever again

It's rubbish on pretty much any objective level but The Replacements is a film I could watch over and over again.

If it was a film that is objectively good then either 12 Angry Men or Casablanca. I think the latter probably has slightly more value for repeated watching but the former is simply an exceptional film.

I'm a little surprised not to see more love for the Shawshank Redemption - regularly recognised as an all time great film but not perhaps the most watchable on a repeating basis.
 
I read the question as 'films that you wish you could erase from your memory and enjoy for the first time all over again'

I'd put Pulp Fiction, Usual Suspects and Memento in this category.

Films that make me feel good no matter how many times I watch them are Almost Famous and Eternal Sunshine of the Spotless Mind.
 
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