I'm not a die-hard Caddyshack fan. As much as I enjoy pointlessly killing time in ugly pants, I don't play golf, but the movie doesn't require any tremendous knowledge of the game to enjoy it, nor must one find themselves playing golf in order to find opportunity to quote the movie.
I really don't know when the last time I watched Caddyshack, but it's been at least a decade. Possibly two.
The movie offers up a great snapshot of comedy in the US circa 1980. Chevy Chase at his Vacation-era best, Bill Murray doing that thing, Ted Knight as Ted Knight, Rodney Dangerfield as Rodney Dangerfield, Harold Ramis directing, Bryan Doyle Murray playing Bryan Doyle Murray and also lending his talents to the script. And let us not forget Cindy Morgan, who totally made sense in context.
Perhaps one of the things that marks the movie as a product of the 20th Century is that it's still a "little guy versus the establishment" movie. We really are no longer fans of what I'll call The Bugs Bunny Idea. In 2015, it wouldn't just be taken for granted that a moneyed judge was uptight and a bully. He'd have to do something evil and underhanded instead of just showing up and showing off his privilege. Sometime circa 2003 we kind of decided we either did identify with the privileged character or strove to identify with privilege as ballers and players or whatever we're calling ourselves these days. But the 20th Century wasn't that kind of era. Bugs Bunny was the guy who didn't have a lot, and certainly didn't appear to have the upper hand when Elmer Fudd came around with his hunting rifle and rabbit season on his side. And when you have a Great Depression on your hands, it's a lot easier to identify with the guy who only has a carrot and his wits to overcome challenges.
Right on the poster for Caddyshack it states "Some People Just Don't Belong!", and an alternate tagline promises a battle for "The Snobs Against The Slobs!" It's stuffy Ted Knight versus the freewheeling, coked-up Chevy Chase and the beleagured Danny, who isn't going to school, is one of thirty kids, and can't catch a break. The caddies' survival (and the grounds keeper's) is dependent on the largess and extra spending power of the wealthy, creating the power vacuum between the two.
I have to assume that in 1980 as we struggled through a bit of inflation and the ripples of the Carter-era recession, even middle class folks were pretty aware of the discrepancies between their suburban households and the mansions, and The Bugs Bunny Idea still held pretty well. Now, I'm pretty sure the plot would be tortured to explain why the two groups seemed at odds. While I'm not one to promote class warfare, I'm also not sure what it says when we've lost The Bugs Bunny Idea. It seems like we got talked out of something kind of important somewhere along the way.
All in all, though, the movie holds up. You can't say it isn't formulaic, but the plot isn't really the point. It's a goof and a chance for the personalities to share screenspace. You always want more movies like this, but they do try, and it doesn't work out super well every time, especially when they attempt a sequel no one was asking for.