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?"
“Most men lead lives of quiet desperation and go to the grave with the song still in them.” --Henry David Thoreau