I would venture to say that the best golf movie is caddyshack hands down. With the classic bill murray, rodney dangerfield, and chevy chase, it was obviously going to be a box office hit. There hasn't been much to come since then that was even nearly as good as caddy shack. That little gopher or whatever it is that bill murray tries to run around and blow up the entire movie makes me laugh just to think about. And Happy Gilmore is up there somewhere too. Just a different twist of comedy, but monumental nonetheless.