The Princess Bride is infinitely watchable and enjoyable every single time.
OMG YES!!! There are so many great things in that movie, such as... The battle of wits: Andre the Giant rhyming: The swordfight where the actors actually had to learn fencing (all the swordfighting was done by the actual actors, the flips and such were stunt doubles.)
I could watch Transformers 1 and 2 and Iron Man over and over. I think that movies that end dramatically or lets say someone dies, those are harder to watch several times. Maybe because you know what will happen and it makes you sad and not encouraged to keep on watching. I'm not really sure but it could also be if there is a big obstacle on the way to the goal in a movie it could be harder to watch over and over because even if you know that something good will happen you don't really want to experience these hard things again.
Zombieland, funny/horror movie, but if scaled, funny would be the benefactor. Grown ups is another, its for the whole family, and the Other Guys is in my opinion, a hilarious buddy cop movie.
Could watch these 3 over and over again for a long time.
there's only one movie that i can watch over and over no matter how many times i watch it i dont know why but i can continue to watch it lol its 8 mile with Eminem in it i dont think he would be my fave artist i just think that hes a good actor for the great movie