Personally, The Rocky Horror Picture Show.
I knew it was going to be quite the experience before I went for the first time‡ but it was so much fun I had to keep going back bringing friends each time.
It’s still a fun tradition to do though we haven’t done it since last year, we’re probably going to try and go again in a few weeks.
‡ I had seen it many times before going to see it in theaters for the first time.
That best my top movie. Which is also Matrix, but I only saw it 3 times in the theater.
Cinema around 12 times (best friend was a Cinema manager back then), the rest at home. Occasionally I throw in the Blu-ray and watch it from time to time…