I figured Caddyshack was going to win because let's face it there are very few movies that you could put up against it and win. The only way Caddyshack loses one of these is if we pitted it against a will ferrell film. Elf or Ricky Bobby would blow Caddyshack out of the water.
The **** they got away with in Airplane! would never even be attempted these days. The subtitles for the two black guys who are "shooting the breeze." The newsstand with a section called: wacking material. lol Airplane! was ahead of its time.
I don't golf, so maybe that's why I don't love Caddyshack, I do however love movies about gladiators. And this is Comedy Gold (minor spoilers-BUT WHO THE HELL HASN'T SEEN AIRPLANE??): Spoiler
Tough. Both movies represented the gold standard of their era, but I probably would choose to watch Caddyshack if both were on TV at the same time. Try telling that to George Zipp
Just on pure volume of the gold, as well as the fact that Airplane! was the innovator between the two, it has to be Airplane!. Caddyshack was great, but Airplane! exists on a higher level of importance, so to speak. Caddyshack was a funny movie, but it didn't break any new ground. Airplane! was the first of its kind, and Hollywood has been copying that template ever since. Airplane! in a landslide.