I would think it would be the other way around since Caddyshack has crude humor that appeals to younger people, while Office Space is more relatable to people +30 that have worked in an office before.
Caddyshack "What an incredible Cinderella story, this unknown comes outta no where to lead the pack, at Augusta. He's on his final hole, he's about 455 yards away - he's gonna hit about a two-iron I think. Oh he got all of that one! The crowd is standing on its feet here, the normally reserved Augusta crowd - going wild - for this young Cinderella, he's come outta no where, he's got about 350 yards left, he's gonna hit about a five-iron, don't you think? He's got a beautiful backswing - that's - Oh he got all of that one! He's gotta be pleased with that, the crowd is just on its feet here, uh - He's the Cinderella boy, uh - tears in his eyes I guess as he lines up this last shot, he's got about 195 yards left, he's got about a - its looks like he's got about an eight-iron. This crowd has gone deathly silent, the Cinderella story, outta no where, a former greenskeeper now - about to become the Masters champion. It looks like a mirac - It's in the Hole!"
Office Space******* The first 90 minutes or so of OS might have been the funniest thing ever put on film. Course they had to ruin it by trying to insert some kind of plot. I haven't seen Caddyshack though, so OS gets the nod. I still can't belive Airplane didn't win this whole tournament. How the heck did that happen.
Office Space This is a comedy for everyone who has worked in a crummy job, got downsized, stole from the company and wanted to destroy either the fax machine or the !#@^ing copier.
20 minutes left. Office Space is making a run down the backstretch. Caddyshack - 23 Office Space - 27