In high school I thought Hamlet was a comedy. All the characters seemed deluded to the point of foolishness. The ending is a perfect comedy of errors. My feeling was good riddance!
Comedy and Tragedy are a matter of perspective. I've seen Titus Andronicus performed as a comedy (And also as a comedy cooking show) - what seems dramatic can also seem melodramatic as a matter of portrayal. The darkest of realities can be the lightest of jokes, ever heard a dead baby joke? Likewise, most good comedy has a serious core at it's center. I have no doubt that by changing the stakes slightly, Caddyshack could be a serious statement on the human condition: Make the scholarship the make-or-break for Danny's college chances, put Spackler on the edge of feeding his kids. Comedy and Tragedy are simply how much distance we put between ourselves and the characters.