When I was a kid, Nightmare Before Christmas. Must've convinced my parents to take me to see it at least eight times. I've watched it at least once every year since then, and it stayed my favorite movie for most of my life, until Everything Everywhere All at Once finally usurped it almost 30 years later. Saw that in theaters four times.
Oh, and Lord of the Rings. Saw all three in theaters at least three times each. And, for some reason, Superbad. Went to five showings of that.