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Most watched would be The Rocky Horror Picture Show by far, particularly when I include all the times I went with friends to midnight audience participation sessions. I've watched the 'original' Batman movie (i.e., the Adam West one [yes, I really mean the Adam West one]) a disturbing number of times, because they always played it last at the dusk-to-dawn drive-in sessions in my hometown. I've watched The Life Of Brian and Monty Python and The Holy Grail a lot of times. Definitely The Princess Bride as well.