There’s a good set of movies I rewatch a lot so I can’t say which is most often, but I’ll pick a couple.
The first Matrix movie is up there for me. I think it’s the best one and I’ve rewatched it the most. I’ve rewatched the following two, but not as much. I thought the fourth one was weird and produced too late so not going to watch that one again.
There’s an obscure movie called Hunter Prey (2010) that I’ve rewatched a lot. It’s a low budget sci-fi, but it’s almost like a play with limited settings, just a handful of actors, and limited special effects. I really like the story, actors, and setting plus the music is good. Probably most people would think it’s shit, but sometimes a low budget film can really nail it for me.