I don't think I've watched a movie more than 3-4 times. Shawshank Redemption is one and the one below is another I've seen several times.
Another I have watched more than 10 times...
Same goes for Back to the future films.
Infact I can't think of a film that has been out in the last 5 years I have seen more than twice. Last films I have seen a few times are the American pie films.