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.
Honourable mention to Love Actually; thanks mum.
I’ve probably seen LOTR: Fellowship of the Ring at least 20-30 times. I’m guessing 15 or so for two towers, and 10 for ROTK.
But FOTR is the perfect movie and I could watch it again and again on repeat if I had to.
For me, it’s Teenage Mutant Ninja Turtles (1990). I was a huge TMNT fan, and I wrecked that tape by watching it so many times.
The Room actually. I feel obligated to show it to everyone, particularly with Rifftrax commentary.
Groundhog Day (somewhat ironically) and Ferris Bueller’s Day Off
I think I’ve watched Jaws 30-40 times. I used to know it word for word.