I think I have watched the first two Terminator films an unhealthy amount of times, but I can't help it when they are just so damn good.
Anyway, I don't count how many times I've watched films but I think outside of the terminator the films I have watched most would be.
Waynes world 1&2,
The Naked gun trilogy,
The original Star Wars trilogy,
The Monty Python films,
Father of the bride 1&2 (under-rated comedy),
The man with two brains,
The Jerk (In fact most Steve Martin films, I think I may just have all of them on DVD),
Die hard with a vengeance,
Baseketball.