Pee-Wee's Big Adventure vs. Caddyshack - X versus Y

At the exclusive WASPy Bushwood Country Club, a young caddy named Danny (Michael O'Keefe) sets out to win the caddy scholarship. Winning that scholarship would be his ticket out of permanently working in a lumberyard. In order to secure his chances, Danny must get in the good graces of the snobby Judge Smails (Ted Knight) and win the caddy golf tournament which the judge sponsors. Danny also finds himself in a love triangle and faces many foes during his stint at Bushwood. Aside from the stiff WASPs, the club also has a few peculiar regulars. Chief among them is Al Czervik (Rodney Dangerfield), a nouveau riche land developer who want to turn the club into a condo complex, Ty Webb (Chevy Chase), the Zen quoting playboy son of the co-founder of the club and the gopher-fixated groundskeeper Carl Spackler (Bill Murray). Al goes out of his way to get under the Judge's skin. After a lot of shenanigans, the two decide to take it to the course in a winner-take-all match.

All's well that ends in a Kenny Loggins' song. Harold Ramis really set the bar high with this classic. Simply, this is one of the funniest movies of all time. Who doesn't love Caddyshack?

Memorable dialogue:

Ty: I like you, Betty.
Danny: It's Danny, sir.
Ty: Danny. Danny, I'm going to give you a little advice. There's a force in the universe that makes things happen; all you have to do is get in touch with it. Stop thinking...let things happen...and be...the ball.

Czervik: Judge, give someone else a chance! You lucky devil! Come here, honey! And loosen up! You're a lot of woman, you know? You wanna make 14 dollars the hard way?
Mrs. Smails: You...you...you're no gentleman!
Czervik: I'm no doorknob, either.

Carl Spacler: Cinderella story, out of nowhere, former greenskeeper, now about to become the Masters champion. [swings, pulverizes yet another flower] It looks like a mirac- it's in the hole! It's in the hole!