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Which film have you seen the greatest number of times?
(kbin.social)
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By choice? Monty Python and the Holy Grail or Fired Up. I watched them both roughly monthly for a half a decade and could recite them both nearly line for line in high school.
Under duress? Spirit: Stallion of the Cimmaron. It was the only movie in my dad's SUV for about a decade and I've probably seen that movie more times than literally anything else because of that.