My record was 43 times for Star Wars (it happened to hit when I had first moved to Reno, didn't have any friends or anything else to do. The theatre was a stone's throw from where we lived and a cute usher would frequently let me in for free), Batman (with Michal Keaton) about 50 times and, of course, Rocky Horror. I couldn't even guess how many times I've see that, but it has to be nearly 100.
How about you?