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Rewatchability is a big factor in this list, skewing results away from movies I love, but don't want or need to see over and over.
Animal House
Apocalypse Now
As Good as it Gets
Better Off Dead
The Big Lebowski
Blues Brothers
The Godfather
Fight Club
Jerry McGuire
Kill BIll I & II
Monty Python's Holy Grail
Noises Off
Pulp Fiction
Raising Arizona
Say Anything
School of Rock
South Park - Bigger, Longer, and Uncut
Pink Floyd - The Wall
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We need the kind of courage that can withstand the subtle corruption of the cynics - E.W.
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