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Already mentioned by Kramus, but I never get sick of watching Groundhog Day, but the topic begs the question "How many times must you see the movie to come to the conclusion that you 'never get sick of' it?"
Groundhog Day: I have seen it ~12 times. I'm not sick of it yet.
Mary Poppins: A great movie to my way of thinking, but after maybe 30 viewings, I want to hurt myself every time I see it. At 20 times, it was still palatable.
The Sound of Music: ~15 viewings and I'm tired of it. It doesn't make me want to hurt myself though.
Shrek: ~25 viewings. Same reaction as above, but not as good of a movie. I was sick of it around 15 viewings.
The Incredibles: ~15 viewings. I'm starting to get sick of it, but I still really like specific parts of it. (Especially the Edna Mode character).
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