[imported_The Vibesman]

Office Space and Lebowski was an easy choice for me, I am just not a huge fan of Office Space. I will usually watch and laugh through the first 45 minutes or so on TV, but the last half of the film always loses me. Lebowski is, IMO, sublime comic genius. Tough one for me was Groundhog Day vs. Holy Grail. They're funny on such different levels that I have a rough time comparing them. Eventually I went with Holy Grail for pure belly laughs, and for virgins asking to be spanked.
Airplane vs. Caddyshack was a bit tougher as well, but I've always been a fan of ZAZ movies, so despite the love I have for Rodney Dangerfield I went with Airplane.