I don't often watch a movie more than once. At least not intentionally. I will watch bits and pieces of a movie a second (or twentieth) time with DH but as for sitting down with the intention of watching it again, it rarely happens for me. I also don't read a book more than once. As soon as I know what will happen I just have no need.
Anyway, one movie I have watched many, many times is Dirty Dancing. I stopped counting how many times I had seen it when I hit the 100's. It really is my favorite and, for some reason, it doesn't matter how many times I see it or if I can recite it or not it still seems new to me every time.
I did see a LOT of great movies on your lists though. Some of my favorites on there are Everafter (DH bought me that one, I don't recall ever watching it after he bought it for me but I LOVED it the first time), Coyote Ugly (listen to the soundtrack a lot still), National Treasure movies, You've Got Mail and Avatar. I also like When Harry Met Sally and I know I've saw that one more than once because I watched it once with DH.
Angie mentioned Breakfast Club. That is a movie we've watched together more than once. Back in high school we had this group of kids in our physics class. I graduated a year before DH so this was his junior year, my senior. Anyway, for his English class in senior year he wrote a comparison of our group to the gang in Breakfast Club. In his paper he compared himself to John Bender and me to Molly Ringwald. We still laugh about it because in the end we got together and those two got together at the end of the movie.
