I'm late as usual, King Friday.
I came up with 25 and winnowed from there...
10. Fight Club
09. Reservoir Dogs
08. The Good The Bad and The Ugly
07. The Blues Brothers
06. Monty Python and the Holy Grail
05. A Night at the Opera
04. Caddyshack
03. Glengarry Glen Ross
02. Do The Right Thing
01. 2001: A Space Odyssey
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The 10 that came up short and why...
10a. The Matrix (doesn't hold up as well after multiple viewings)
09a. The Killer (goofy dialogue)
08a. Amores Perros (goes a bit too long)
07a. The Princess Bride (Columbo and Kevin)
06a. Blazing Saddles (ending gets ridiculous)
05a. O Brother Where Art Thou (too aware of itself)
04a. South Park: Bigger, Longer, and Uncut (not enough Terence and Philip!)
03a. Fargo (no good reason)
02a. Shaft--the original with Richard Roundtree (not enough action, the acting is awful, and you see Shaft's ass; however, if it's on, I must watch it)
01a. Adaptation (devolves into a standard Hollywood ending--which is really the point if you've paid attention. still, it does stand as an excellent commentary on the "art" of screenwriting vs. the "biz" of moviemaking)
And 10 to grow on...
Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb
I'm Gonna Get You Sucka
The Breakfast Club
The Truman Show
Raising Arizona
The Wizard of Oz
Being There
Jungle Fever
Pulp Fiction
Memento
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