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Yes. The thing about Happy Gilmore that just makes it a better movie overall is that there are multiple story lines to it. The grandma, the hockey, the PR lady he's trying to swoon, the villian (Shooter), the boss w/ a nail in his head, CHUBBS, the alligator, Lee Trevino and the love for Top Flite, miniature golf, Bob freakin' Barker, etc etc etc. .
I would say it could go north south too since Happy Gilmore has a lot to do with hockey.
Happy has my vote.
"Son what the H*ll are you doing?"
"364 more days till next years hockey tryouts I gotta toughen up"
"During high school, I played junior hockey and still hold two league records: most time spent in the penalty box; and I was the only guy to ever take off his skate and try to stab somebody."
"Is that net regulation size or what? Jeez."
I love both, but voted Caddyshack. The candy-bar in the pool scene can make me laugh for hours. I'm laughing right now thinking about it.