TOD: As much as I wanted to be among the ones who professed to seeing "The Sound of Music" hundreds of times, I believe I only managed abuot six viewings of the film in its initial theatrical run.
That said, I worked as an usher during summer/fall/early winter of 1965 and the one film I saw the most while working was "The Yellow Rolls-Royce", which I viewed straight through about 13 times.
Home video is something else again. I've held annual marathons over the years during which I watched all the "Rocky" films, all the "Die Hard" films, all the "Lethal Weapons" films, all the Astaire-Rogers films, all the "Star Wars" films, etc., etc., etc. I couldn't even begin to speculate how many times I may have seen any of those films.
Over the last decade, the films I've watched more than a few times include "Meet Joe Black", "Field of Dreams" and the "LOTR" trilogy.