The only movie that I actually laughed so hard that I cried was Bruce Almighty... you know the part... Where Jim Carrey makes the guy from "40 year old virgin" go insane infront of the camera and he gets fired. That part is pure comedy gold.
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It's so hard to narrow it down to one movie.....some good ones have been mentioned already in this thread (Dumb and Dumber, Zoolander). For me it's a toss up between Old School, Trading Places and So I Married An Axe Murderer.