The most extreme I've ever gone with one is Hot Rod. I feel like "I've seen it easily over one hundred times" is usually seen as hyperbole, but I am being completely genuine when I say it. There was a period when I was in middle school for a month or two where I would get home from school and just go "guess it's time to watch Hot Rod again" every single day.
Though I haven't reached near those heights since then, some more recent ones for me would probably be Tremors and Saw. I've also seen Con Air quite a few times.