Have you a movie/movies that you love so much you'll happily watch/listen to more than once within a week? There's an Irish animated movie called Song of the Sea, and I love it so much that when I watch (though mostly listen to whilst I train) it, I'll put it on again the next day or a couple of days later. It's such a lovely story and the animation style is so pretty!

https://en.wikipedia.org/wiki/Song_of_the_Sea_(2014_film)

Lilo and Stich and Ten Things I Hate About You are my go-to "in the background" movies that I watch more times per year than I want to admit. Lmao.

Shaun of the Dead. Don't ask, I don't know why I'm like this D:

Oooh, Ten Things I Hate About You for sure. Also massive LOTR nerds so we watch the entire extended trilogy usually 2x yearly, once at christmas (just about to start!) and once in the summer.

ETA - Skell, Shaun of the Dead gave me zombie nightmares for ages after watching it (aged 11, tbf), even though it's meant to be a comedy xD

Labyrinth is my favorite movie of all time and The Princess Bride is the perfect movie in my opinion, so I definitely watch those two multiple times throughout the year. I'm a creature of habit so I tend to just watch my favorite movies/shows rather than new ones, I'm terrible. =)

When I lived in a little house alone in the woods, I had no cable and just DVDs. I loved the Shawshank Redemption and it was my go-to movie for background noise or white noise while I slept. That DVD must have played three million thousand times... I finally got satellite lol 

Disney's Aristocats, for sure. and High Society. And I could watch 13 Going on 30 every month or so, but maybe not more than once a week, if I had to.

The Pirates of the Caribbean (the first 3) movies are ones I could watch on repeat. I think the music is a lot of the reason for that. ^^

Any horse movie (Spirit, Black Beauty, Spirit Rider, Coyote Summer, Misty, Breaking Free, Nico the Unicorn, The Little Unicorn, The Black Stallion, The Princess Stallion, Dreamer, Shergar, Seabiscuit, Secratariat, etc I have a ton more!)