I don't rewatch movies near that much, some I'll watch once or twice a year.
Planes, Trains, and Automobiles
Robocop
Police Story
The Crow
Christmas Vacation
Those are a few I haven't gotten sick of despite watching them atleast 15 times.
I see a few mentions of The Breakfast Club, just saw that for the first time less than a year ago and was thinking about rewatching it.
Also My Cousin Vinny which I'm going to see for the first time soon. Didn't like the movie when I was like 11 and don't think I ever watched the whole thing.