Yeah the key thing for owning a movie is does the movie warrant and/or stand up to multiple viewings. But there are so many different reasons why a movie would be rewatchable. Here's a list and why I find each one rewatchable.
Mad Max Fury Road. This is the only movie where I watched then immediately went back to the beginning and watched the whole thing over again. There are so many reasons to rewatch: amazing cinematography, great sound design and sound track, mind blowing action sequences, subtle world building and small details you can pick up in later viewings.
Chicago. I think musicals are inherently rewatchable if it has catchy song and dance performances. And Chicago has that, plus a cool vibe and great performances throughout.
Aliens. I can't even count how many times I've watched this. Just a perfect action flick. I might call Alien the better movie, but I've watched Aliens a lot more.
Tremors. Another movie I've watched a billion times. I just love stories that involve everyday people working together to survive extraordinary situations. So many great characters, scenes, and sequences. The Rec room scene is worth it alone.
Lion King. One of my most memorable theater going experiences. I felt I got my money's worth just in the opening sequence. And another case where the music alone makes the movie infinitely rewatchable. You could probably add several movies from this Disney era: Little Mermaid, Beauty and the Beast, Aladdin, etc - but this is my favorite of the bunch.
Matrix. Spectacular visuals, action sequences, and world building. Its one of those movies that really requires a couple watches just to fully understand, and you can pick up other details with each additional viewing.
Brazil. If you put Monty Python into a dark dystopian nightmare world you get "Brazil". Many interesting shot choices, but its the dark ironic comedy and social commentary that keeps me coming back for more watches.
