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Comedies are tough..

Airplane!
Monty Python
Princess Bride
Hangover
Sandlot

Yeah, Airplane. Silly as hell,but was brilliant because they got a bunch of dramatic actors, many of whom started in some of the disaster movies of the '70s, to be in a movie spoofing disaster movies.

In no real order of favorites...

The Big Lebowski
Dirty Rotten Scoundrels
Tropic Thunder
Mash (the movie)
Catch 22 (although somewhat a dark comedy)
Most of the Cohen Brothers comedies, particulary Fargo and Raising Arizona, and Oh Brother Where Art Thou
And can't leave out Animal House
 
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Also big on Christmas Vacation.

Haven't seen in years but Tropic Thunder had me laughing the entire time. Not sure how it would stand up now.
 
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