I agree on "The Greatest Game". It works because it's a drama - like a courtroom drama, e.g. The Verdict - that just happens to take place on a golf course. Its dramatic foundations/engines are as old as the sun: the underdog, the fish out of water, the coming of age, the father-son, the redemption. I like the mystical side of golf as much as the next fellow, but that approach doesn't work for the medium of film; it's best left to novels or poetry, where the mysticism is embedded in language itself and in the imagination responding to that language. (I can go on and on about how some golf architects make the same mistake, for my tastes.)
I also agree on Caddyshack - sometimes funny, mostly boring and often annoying. I think it's because I've never been a big fan of Bill M on film; there is always an under-current/unconscious level of anger in him. Nothing wrong with anger, per se, but I like mine more open and honest and direct, as in a Joe Pesci performance in a Scorcese film.
P