Which film have you seen the greatest number of times?
I've definitely seen The Prestige (2006) the most in my adult life, it was my taste-barometer when showing a new friend or date when I was in my 20s.
But we had the The Mummy (1999) recorded from TV on a VHS growing up and I recked that shit. I probably watched that film 30-40 times, between childhood days off sick and rewatching intermitently in adulthood.
The Blues Brothers is one of my all time favorite movies. I got some beefy speakers and the neighbours have been enjoying this movie with me many times.
Somewhat unusually I enjoy BB 2000 as well, it would be unfair to expect it to be as good but it's a nice movie, except for the ridiculous zombie playoff part.
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.
The Lost Boys, cheesy vampire movie from the '80s. I used to watch it every night when I was a kid, and I still watch it every now and then. I've probably seen it hundreds of times.