This often gets comments about whether or not I actually watch the movies I own, more than once.
Now, I think any good film is re-watchable. However, some movies are massively re-watchable.
Here's a list of some of the films I own that I consider to be the most rewatchable.
I like to joke that I can watch Groundhog Day over and over and over again, but really it is true. Something in this film speaks to me. The premise is fantastic (if not 100% original), the humour is pretty solid, and the film has real heart, without getting too mushy (although it's a bit mushy). Anyway, I think this the number one film in my collection that I am always willing to watch, even if I have recently watched it.
The Rocky Horror Picture Show
I first saw Rocky Horror on TV, and knew it was special. Then a few years later, I rented the video, watched it, rewound it and watched it again. I think I watched it about 20 times before the weekly rental was up. Then I discovered the joy of seeing this film at the cinema, with audience partici... pation. Of course, sadly, it's been about eight years (gasp) since I've been. I really should go back.
The Princess Bride
Do I really need to talk about this one? If you go by my peer group, this is easily the most popular film of all time. It is quite possibly the most quoted film of all time. I feel a little sorry for Wallace Shawn, he must get the word "inconceivable" yelled at him all the time. Then again, that might actually be kind of cool.
The (original) Star Wars and Indiana Jones trilogies
I'm lumping these two together because the reason they are re-watchable is the same for both. Good, old-fashioned, "swash-buckling" entertainment. These movies are just plain fun, and I think that, in a nutshell, is why they have endured so long with such a following, and pretty well sums up the reason why the Star Wars prequels just don't cut it.
The Emperor's New Groove
Family-friendly cartoons (ala Disney, Pixar and Dreamworks) are pretty re-watchable as it is. The Emperor's New Groove is absolutely, hands-down, the best of the bunch. Yes, that means I am claiming that it is better than Aladdin, The Lion King, Shrek, Toy Story, etcetera. Just watch it; you won't be sorry.
The Big Lebowski
Fuck it, Dude, let's go bowling.