For some reason I actually didn't watch the full-length unedited Caddyshack until I was in my early 20s/the mid 90's. I did not find it nearly as funny as my older friends who had seen it many times.
The first time I saw Office Space I really enjoyed it - definitely more than Caddyshack.
But the edge here overwhelmingly goes to Caddyshack purely on replay value. Caddyshack gets better each time you see it and I think it has aged extremely well - unbelievably tough to for a comedy to do.
I actually saw Caddyshack 2 in the theater. Bringing up that movie to a Caddyshack fan is like the time at work a co-worker of mine said he was seeing Styx in concert. At the fair I presume
And my response was "Ohhhhhh, you mean that group that did Mr Roboto?"