This is odd, because I can't think of a single film I've watched more than five times of my own accord except one. That one would be the 1963 Jason and the Argonauts, which I've seen perhaps ten times overall. The two next closest - half a dozen times each - have been Galaxy Quest and Down Periscope, which are family favourites, so don't necessarily count.

Other than that there are the 'Bank Holiday' films. The ones that turned up regularly on TV at Christmas, Easter and on the Whitsun and August Bank Holidays. Zulu, El Cid, Ben Hur, Where Eagles Dare, The Guns of Navarone and so on.

I am not counting 'films that were on when I was in the room', because I was usually buried in a book while other people were watching them.

Then again, I've never claimed to be a cinephile! The number of books I've read multiple times is a different matter!