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.
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I only usually rewatch films whenever I feel like I’d need a pick-me-up. Something light-hearted, so I’d usually go for The Secret Life of Walter Mitty.
But during my recent movie marathon, I discovered more films which are actually good contenders for a rewatch such as The Fundamentals of Caring (highly recommended) and The Land of Steady Habits.