I reckon I watched the VHS edition about 30 times...then the original DVD another 10 times or so...and then the special edition DVD with commentary perhaps another 10 times.
For me it tenRAB to be films with either visual flair or a good soundtrack or both. The experience is a bit like playing music or having a picture on the wall. It's comforting rather than new and surprising.
Examples for me include:
Hero
Silent Hill
Moulin Rouge
I do, however, get bored of them eventually. There are a few films I loved when I was young, and watched a lot, but don't even own now because they are all watched-out. Blade Runner is an example.
Christmas films will be watched over and over again in our house and as we have many of them, for example just about all the Scooge films that have been made (cartoons, musicals the lot) We start watching them in August (one/two per week) to get them all in before the big day. I like "Scrooged" with Bill Murray and watch that one all year round.