There are several that you have to watch multiple times to just try and keep up with the jokes:
Planes, Trains and Automobiles--Steve Martin's scene at the counter where he drops the FBomb about 30 times is an all time great scene.
Airplane--Is there a funnier movie?
Three Amigos--Truly just an awesome show.
Anything by Christopher Guest but specifically Spinal Tap and Best in Show.
As mentioned, some other very funny movies include Old School, Hot Shot, the Jerk, Office Space, Young Frankenstein and Fletch.
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