Personally I don't re-watch a ton of movies. I have a meager movie collection, basically takes up 3/4's of a standard, 6 foot tall, bookcase, mixing regular movies with anime, and some concert stuff. I love watching new stuff, and while I do buy some to put into my collection, I only go back to certain movies on occasion. I was realizing that there were certain ones I very much put in like once or more a year sometimes and that I've probably watched them a lot.
My first movie is Legend of the Drunken Master or just Drunken Master 2. Possibly Jackie Chan's best movie. The action in it is next level good. Like I think I could almost say that there wasn't action that good again till like...The Raid in recent years. I might be exaggerating slightly, but man Jackie Chan back then was incredible.
Another in a more feel good way is the old Disney Robin Hood cartoon. I use to work at Blockbuster in the early 2000's, and there was always a movie playing if we didn't have the usual advertisement stuff going. Generally we couldn't put on anything really higher than G-rated, PG if it was more due to action and such, but a few movies got put on regular rotation. Sometimes it burnt the movies out for people, like Aladdin, I watched that a ton. Robin Hood was always a feel good movie and I watched it not too long ago again on Blu-Ray and it holds up just right for me. It's such an enjoyable and chill movie.
Sidenote, is there a good video list website like this place is for videogames or My Anime List is for Anime? Don't need anything fancy or for the community aspect, just for basic tracking. I feel like there are some movies I'd like to start collecting and it would be nice to keep track of them.